sailing trip

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North America

Central america & caribbean, south america, north africa & middle east.

Few travellers make it to this icy continent, but the lucky ones who do get to explore a frozen Eden ruled by the elements and teeming with wildlife.

G Adventures Land

G adventures sailing & cruises, g adventures private travel.

Whether it’s a family retreat or a girls trip, you can surround yourself with a hand-picked crew and customize a tour that fits you all perfectly.

The Geluxe Collection

Our new line of premium active adventures is officially here. With perfectly paced itineraries, one-of-a-kind accommodations and elevated dining, this is adventure at its finest.

National Geographic Journeys

Go deeper into the cultures and habitats of the places we explore. More is included and you’ll enjoy greater hands-on exploration, interactions with local experts, and freedom to roam.

National Geographic Family Journeys

Are you an adventure-loving family in search of meaningful ways to discover the world together? These tours are specially designed for travellers seven and up and their inquisitive families.

Jane Goodall Collection

Step deeper into the animal kingdom while respecting all of its inhabitants. Our incredible collection of wildlife-focused tours is endorsed by the world-renowned ethologist.

Roamies by Hostelworld

The thrill of adventure. The awesomeness of hostels. Get ‘em both on these immersive small group trips for 18 to 35-year-old travellers.

Why choose us

As the leader in small group travel for 30 years, we know how to do it right: flexible itineraries, freedom to roam, safety, peace of mind, and locally based guides.

Change the world just by having the time of your life. When you travel with us, you become a force for good by acting responsibly and creating positive impact.

Together with our non-profit partner, Planeterra, we ensure local communities touched by our tours benefit from our visits in as many ways possible.

Trees for Days

Leave your destination even greener than you found it! For every day on tour, we’ll plant a tree in your honour and ensure that our forests get to live their best lives.

Travel resources

Last minute deals.

Looking to have the time of your life in the next 90 days or so? You can save big if you’re ready to book now.

Loyalty discount

Back home from a G Adventures tour? Submit a quick trip evaluation to save 5% on your next tour with us.

Student discount

Got proof that you’re pursuing higher learning? Then we’ve got a travel voucher with your name on it.

All travel deals

New ways to save pop up all the time. Here’s where you’ll find every hot deal in one easy place.

The greatest adventures on surf

No matter how far inland we live, there’s something about the sea that calls to us. It’s wide. It’s deep. It’s blue. It’s a canvas upon which we can paint adventures we otherwise can’t do on dry land. Okay, so you probably don’t have your own private yacht waiting to spirit you away to distant shores. But we do. Plenty of ‘em. (And a couple of catamarans, too.) Climb aboard and explore the Greek Islands, the Turquoise Coast, the Adriatic, the Andaman Sea, and other exotic places with a small group of fellow adventurers and a skipper who knows your destination’s every isolated cove, pristine beach, and secluded coastal village. Billions of years ago, we emerged from the sea. Isn’t it time you went back?

Where can I sail with G Adventures?

Canary Islands

Sail for seven days aboard our 15m (52 ft) yacht, with time for hiking, snorkeling and relaxing.

Croatia & Montenegro

Italy & Croatia

Discover peaceful coves, hidden inlets and secluded beaches on this 10-day sailing trip from Italy to Croatia.

Featured Sailing Posts

Sri Lanka and the Maldives: A match made in heaven

From the tea and spice scents of Sri Lankan countrysides to snorkelling from 'home' on a dhoni boat

Written by: Pippa Brumwell , 20 Sept. 2022 10:45 a.m.

Cruise through our Insta-worthy European sailing pics

Set a course for your next adventure with inspiration from our Instagram posts featuring Croatia, Greece and Greenland marine adventures

Written by: G Adventures , 10 Feb. 2021 06:21 p.m.

Top 5 moments on the Greek Islands

It’s the place to slow down a fast-paced lifestyle for a while - and what better way is there to soak up the Greek Islands than by sailboat?

Written by: Robin Wu , 11 Sept. 2020 01:53 p.m.

Sail the high seas from your sofa

Join CEO James for a virtual sailing tour of the Greek Islands!

Written by: G Adventures , 3 Sept. 2020 05:12 p.m.

What’s life like at sea?

Adventuresome days.

Squeeze the most adventure out of every port stop. With no fixed itineraries, you’re free to explore on your own terms and at your own pace. Each stop will bring you to great restaurants, scenery, lively entertainment and closer to the culture as it’s lived everyday.

Relaxing nights

By night, our boats anchor in the most beautiful bays and picturesque harbours you’ll find. Sleep in your bunk or camp out on the deck under a blanket of Mediterranean stars. The choice is yours.

Small groups

We believe that small is best when it comes to group size on our yachts, so that you can get the attention and service that you deserve. No more than nine people will be on any boat, including the skipper.

Sample the fabulous fare of the local tavernas, or maximize your travel budget by pooling your cash with your shipmates and preparing your own meals on board.

Sailing Season is Here. Join Us for a Sail!

Welcome Aboard!

Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II , for a true sailing experience in Annapolis, Maryland.

Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing Capital.” Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay. As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging and enthusiastic. Sail away with us!

Make your sailing experience a memorable one! Sail away with us!

Schooner Freedom Charters

Tall Ship Sailing Daily from Saint Augustine

WELCOME ABOARD THE SCHOONER FREEDOM

**celebrating our 23rd year in st augustine**, our family invites yours to join us on a sail.

Reservations are recommended for all sails Please call 904.810.1010

The Freedom is the largest United States Coast Guard Certified Sailing Vessel in St. Augustine. We are dedicated to providing an exceptional and safe experience to all our guests. We are certified for 41 passengers, but we have reduced our capacity on all our sails to provide a comfortable and relaxing experience  for all.

T he Schooner Freedom is St. Augustine’s Premier tall ship.  76 feet of steel, Freedom was built in Norfolk, Virginia and brought to St. Augustine in 2001 by owners Captain John Zaruba, and his wife, Admiral Sarah.  Freedom is the only schooner charter vessel between Charleston and the Florida Keys.  With nearly 2400 square feet of sail, she is an honorable testament to naval history and to the privateers of the early 1800s. 

Freedom is a gaff-rigged topsail schooner, and a highlight to any Saint Augustine vacation . Family owned and operated, love, grit and honor is poured into every crevice of this ship, and it shows in our Captains’ and Crews’ vast knowledge of sailing history and their deep passion for the ocean.  If you don’t happen to catch Captain John or Admiral Sarah on a sail, chances are one of their children Capt Jack or Sydney will be onboard. Come for a sail on board, learn about the unique history of our nation’s Schooners and beautiful Saint Augustine, the nation’s oldest city.  Hoist sails and enjoy a drink on the waters, you won’t regret it

The Schooner Freedom  has been sailing the waters of historic St. Augustine since 2001 and is listed as one of the top ten attractions in St. Augustine by USA Today. We offer relaxing Day, Romantic Sunset, and Enchanting Moonlight Sails, as well as a variety of special events throughout the year. Our family invites your family to join us for an amazing sailing experience.

Schedule is subject to change.   Call for the most up-to-date information. Reservations are recommended for all sail times. Please call for more information on available sails.

(904)-810-1010

Join us  Aboard St Augustine’s only Tall Ship

  call for future reservations 904.810.1010 or email us at [email protected].

**Gift Certificates Available**

 it’s never to early to book a great day on the water call for reservations and availability 904.810.1010 or email [email protected],                                       “in the heart of old town”,                                                                                                         full moon sail,                                               thursday may 23rd,                                                                             8:45 pm 1 hr 15 mins                                                                                         live music,                                                      $55.00 plus tax refreshments included                                                             **reservations recommended**.

Seating is limited for the Comfort of our guests

Enjoy the beauty of St. Augustine bathed in moonlight, listen to the waves lap the hull or dolphins surfacing. Live music sets the mood. This sail takes place every month on the day before and the day of the f ull moon – keep an eye on our calendar.

***PLEASE NOTE – due to bridge opening restraints we will be sailing south on moonlight and full moon sails.***

Length of Sail: 1 hour 15 minutes

Complimentary refreshments provided.  $55.00 per person plus tax Complimentary Refreshments Included

Limited seating on all our Sails for Comfort

Gift certificates are available either online through our ship store or, by calling 904.810.1010, fins and freedom sail may 17th.

1:15 2 hr day sail

Hosted and   Narrated by Terran McGinnis Local Biologist and Community Educator of Marineland. The best in the area!

904.810.1010

Set sail with Marineland and Schooner Freedom Charters, Inc. for a one-of-a-kind sailing experience! Come on board, help raise the sails, and then kick back and relax while you learn fascinating new facts about St. Augustine’s local marine life and their habitats. It’s very common to see wild dolphins, turtles, birds, and more, on these trips, so come prepared to ask lots of questions! Complimentary refreshments are provided onboard the boat. Passengers may bring snacks or a picnic. Your Fins and Freedom charter includes a pass to use for future admission to Marineland! $60.00 per adult $45.00 per kid 2-16 under 2 free

Learn more about our Fins & Freedom Sail Here

WE ARE DOG-FRIENDLY!!

***** ***Schooner Freedom Charters and it’s employees are not responsible for any lost or damaged items while on board.  Please remember this is a fully functioning working schooner and things move around.  Please be sure to secure all valuab

Dump out your bucket list.

This is the adventure you’ve been looking for..

Windjamming is, quite literally, like nothing else on Earth. By turns exhilarating, relaxing, surprising, and nurturing, it’s like no other vacation you’ve ever experienced.

Wake up to the quiet solitude of Maine’s coast, find renewal in the wind and sun, and surprise yourself as you help steer the ship. Aboard our vessels, with itineraries tossed to the wind, our guests find both a spark of adventure and time to reflect.

Is there a sailor in your soul?

Welcome to the Maine Windjammer Association – the largest fleet of traditional tall ships in the Americas. Our iconic windjammers offer multi-day, all-inclusive, sailing adventure cruises in one of the most acclaimed cruising grounds in the world.

When you sail aboard a Maine Windjammer Association vessel, you can be sure that your hosts hold themselves to the highest standards of safety and quality. As your captain and guide they will treat you to honest, heartfelt Maine hospitality and personalized attention.  Explore our fleet and offerings to find your perfect cruise.

The Windjamming Experience

Simply put, windjamming is about reconnecting with our essential enjoyment of life. It’s about gorgeous scenery, human connection, soul-nourishing meals, and taking time for both adventure and reflection. Our playground is the sparkling sea and the spruce-clad granite islands that rise from it.

Whether you join us for a three-night cruise or a week, we promise you a total escape from the ordinary. Be prepared to get closer than you ever have before to breathtaking wildlife like eagles, seals and porpoises, to visit some of North America’s most spectacular coastal scenery, charming villages and unspoiled islands, and to savor the freshest, fire-cooked Downeast fare. With only 16-31 guests on our ships, you’ll experience the kind of honest, heartfelt hospitality that keeps our guests coming back year after year.

Welcome to the only place in the world where schooners play in abundance. Where steady breezes, glittering bays, and literally thousands of islands make Penobscot Bay one of the most revered cruising grounds on earth.

On our small ship cruises, we have complete liberty to explore secret anchorages, remote fishing villages, and charming gallery towns. Schooners have been an intrinsic part of the Maine Coast for centuries, and there is something very special about rounding the point and arriving at anchorage under sail. Come touch this culturally distinct, pristine and physically breathtaking part of America.

Explore by Schedule

Use our cruise finder below to explore sailing options that fit your schedule. If your dates are flexible, or you just want to learn more, visit our fleet page and each vessel’s website. Reservations can be made directly with the Windjammer of your choice. Have fun exploring! Whichever vessel you choose, you are sure to have the sailing adventure of a lifetime.

Find My Trip

It was a super trip. Beautiful ship, thrilling when under sail. Two gorgeous days and two rainy ones that didn't diminish the experience... relaxing in the cabin and in the galley chatting (and on deck watching the coast go by in the rain.) Excellent food at every (very generous) meal. Friendly crew, friendly passengers... all in all, a wonderful experience.

Stay in the Know

With our monthly newsletter, you’ll receive tips and hints from folks who have sailed as well as information about the best dining and attractions the area has to offer, special packages, windjammer history, events, and more!

You can request a mailed or digital packet of brochures, or you can find individual ships’ brochures under each listing on the fleet page.

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We sail April 19, 2024 to Nov 3, 2024

Sail Selina II

Relaxing chesapeake bay sailing tours, sailboat rides & sightseeing boat trips in st. michaels, md, we sail april 19,2024 to nov 3, 2024, clean & safe, thank you for supporting small business, our popular st michaels maryland sailing charters and relaxing chesapeake sailboat cruises.

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2 Hour Relaxing Chesapeake Day Sail

Want to relax? Join our friendly crew and learn about St. Michaels while cruising in a comfortable well-maintained historic sailboat on the Chesapeake Bay. Enjoy the sun on your face and the wind in your hair as you sit back, relax, and enjoy outdoor scenery on your personalized sailing boat tour!

Chesapeake Bay Champagne Sunset Sail

Experience a breathtaking Chesapeake Bay sunset while savoring a glass of Champagne or handcrafted beer or wine on this romantic St. Michaels, MD sunset cruise. Book now to embark on an unforgettable journey that’s perfect for couples looking for a unique and romantic date night activity.

Moonlight Cruise

Enjoy free Champagne while taking in the breathtaking beauty of a sunset or the rising of the moon on Chesapeake BY aboard this romantic Moonlight Cruise!

• User Ages 21+

St. Michaels Wine Tasting Cruise

Come aboard Sail Selina II in St Michaels MD and learn the basics of wine tasting and sample great vintages with Capt. Iris and her crew during this 2hr outdoor excursion.  Our wine cruise is just an hour from Annapolis, making it the perfect day trip.

Beer Tasting Cruises

Looking for a fun and refreshing way to quench your thirst with a cold beer while exploring the St Michaels area? Sit back and enjoy some great Maryland Craft breweries aboard the Selina II!

Private Sailing Lessons

Embark on an unforgettable sailing adventure with our seasoned team aboard the historic yacht Sail Selina II. Experience the freedom and exhilaration of sailing while learning new skills and building confidence on the water. This introduction to the basics that will transform the way you connect with mother nature.

• User Adults only

Marriage Proposal Engagement Cruise

♥Getting engaged♥? Surprise your fiancé with a nautical wedding proposal on a private yacht with this Engagement Package. If you’re looking for a creative engagement on a boat this is a unique way to pop the question!

• Users 6 or More

Nautical Wedding Package

Looking at weddings on a boat? Get married in St Michaels MD on a sail boat and have an unforgettable nautical elopement or sailboat wedding ceremony aboard Sail Selina’s yacht! You have two wedding packages to choose from:  boat weddings are either a Ceremony Under Sail, or a Wharf-Side Wedding.

Sail Selina Swag

Sail Selina has perfected the art of sailing, and now we’re proud to introduce our collectable high-quality logo apparel that will have you looking as good as you feel on the water.

Best Relaxing Luxury Sail Boat Tours on Chesapeake Bay

Looking for a relaxing Saint Michaels, Chesapeake Bay boat tour? Want to get out on the water, unwind and spend some time in nature? If you’re wondering about things to do in St. Michaels MD or seeking top attractions in St. Michaels Maryland, look no further than the luxury sailing yacht Selina II. Unique, upscale, and exclusive, she limits her passengers to just 6 guests for an intimate taste of the history of sailing.

With freshly varnished mahogany, brightly polished brass, and comfortable seating, let Sail Selina II, the premier sailboat in St Michaels, MD, be your sightseeing charter boat. Hop aboard and experience another time and place.

Come join us outdoors on the water for a relaxing 2-hour sailing trip on this nostalgic river boat cruise. Your St Michaels, Maryland sailboat ride includes a personalized informative tour with our knowledgeable 1st-class captains and friendly crew. We know you’ll love all the boating trips aboard our meticulously-restored historic 1926 sailboat Selina II, including romantic sunset cruises, our super popular day sails, and our specialty outings like sailing lessons, wine tasting tours in St. Michaels MD, beer tasting cruises, moonlight sails and more.

For private sailing tours, the Sail Selina II is docked at the Harbour Inn & Marina in the heart of St Michaels, MD, a charming eastern shore town known for its wonderful seafood restaurants and quaint small-town feel.

If you are looking for day trips to St. Michaels Maryland or if you want a sailing charter on the Eastern Shore of the Chesapeake Bay, Sail Selina II’s relaxing sailboat trips are just 90 minutes from Philadelphia, Baltimore and Washington D.C. and just 60 minutes from Annapolis.

Outdoors in nature, our sailing boat offers your choice of a public or a private boat ride in one of the best places to sail. Chesapeake sailing is known for its beauty and gorgeous sunsets. Your sailboat charter includes a boat sail through the harbor and then out into the Miles River for spectacular views and sometimes even wildlife viewing like Osprey & Bald Eagles. This year there have even been porpoise sightings.

Looking to relax? We are the St Michaels MD harbor cruises to choose!

Learn more about the history of our sailboat and all the fun outdoor activities in St. Michaels, MD here:

The #1 Boat Tour in St. Michaels on TripAdvisor!

A friend was visiting from Baltimore and we went sailing last night for the sunset cruise. It was amazing, the sailboat was gorgeous, the Captain and her first mate were exceptional, and the beauty of the river was breath taking. I am so glad I discovered Sail Selina II, I will be taking many friends and family members on this beautiful adventure when they come to visit me in Easton. Thank you for a remarkable memory and such a beautiful experience.

A golden opportunity to sail on a captain owned historic wood yacht! It was a dog day of August with precious little wind, yet we enjoyed every minute of our trip. Captain Iris was a gracious host, passionate generational owner, not only captain but articulate professor of both sailing and ship building. We highly recommend sailing aboard the Selina ll. The crew is fabulous as well.

Hubby and I spent a sunset afternoon on Selina 2 with Captain Iris and first mate Jesus. We had a lovely cruise drinking champagne and listening to Captain Iris talk about St Michael and the history of her family sail boat. What I loved was she was mentoring a future captain in the making - a twelve year old from the area who wanted to learn more about sailing. This is so worth it and I very much encourage you to go!

My wife and I had a great time on this vintage sail boat. The Captain and First Mate were great hosts teaching us a lot about sailing and the history of the bay at the same time. Loved that the boat holds only six guests at a time, only four aboard for our trip, making it a very intimate experience!

The two hour cruise In the company of Captain Iris, Crewman Chris, and four other guests provided the best evening of our August vacation. The generous hospitality (nice selection of wine and beer if champagne was not your preference) was supplemented by the unexpected and pleasant opportunity to observe several races and Captain Iris was generous with her knowledge of sailing the Tred Avon areas of the Chesapeake. The Salina II will see us again when we return.

Took a moonlight cruise on the Sail Selena II. Had a lovely evening star gazing, sipping wine, chatting with the other couple aboard. Cap’t Iris and her ever so sweet (and personable) first mate were both kind and knowledgeable. We enjoyed the evening immensely. We would recommend this outing without hesitation. Such a great experience!

Being a motor-head all of my life never really let me get the deep appreciation of the sea as I experienced when I sailed on the Selina II. To cruise along with nothing but the sound of the waves, wind and seagulls was a truly eye opening experience for me. Captain Iris was absolutely enchanting with the stories of Saint Michaels and her beloved Selina II. The cruise was intimate with only 2 other couples and was an experience I will long remember.

Captain Iris runs a fabulous operation out of St. Michaels. This was our first time visiting the town and this was such a great way to experience St. Michaels and the Chesapeake. The Sunset Champagne cruise was fun and intimate as only 6 people maximum. The two other couples we met were so sweet. Sail Selina II is a must do in St. Michaels!

Why Sail Selina II?

Rated #1 on tripadvisor.

When looking for things to do in St Michaels MD, o ur reviews tell the story! Limited to just six guests, Sail Selina II is ranked the #1 Maryland sail boat tour in St. Michaels and has been for 18 years running.

Everything Is Included

Sit back and relax. Want a drink? We’ve got it! Cold beer, red & white wines, Champagne, and soda are available for sale on all our Maryland sailboat rides and are included on our evening charters.

Over 96 Years of Experience

Sail Selina’s top-notch skippers have a combined sailing history of 90+ years, and her friendly crew has a combined sailing history of 30+ years. We all love to sail and we love taking people for sailboat rides!

Spacious & Beautiful Boat

All our relaxing sailing boat charters are in a gorgeous setting. Sail Selina II was built as a gentleman’s yacht in the Gatsby era and is finished in freshly varnished mahogany and brightly polished bronze. Her spacious cockpit is the perfect setting for a Maryland sail on the ultimate charter boat in St Michaels, MD. Join us for a sailing charter boat tour and unwind with an authentic taste of the history of sail.

The Best Captains

Our St Michels boat tour captains are known for their storytelling skills and offer a boat trip balanced with some touring, some sailing, and some time to simply relax, unwind and kick back. When sailing on the Chesapeake in St Michaels, choose from a basic sailboat ride, or opt for a specialty outing like a local craft brew beer tasting cruise or a sunset champagne charter.

• Ticketed Cruises

Take to the water and fall in love with NYC from the decks of one of our classic yachts. Renowned for our hospitality and our beautiful and elegant yachts - you can find respite, romance and refinement on all our excursions.  Learn more »

Architecture Tours

Join us for a round-island tour of Manhattan with the American Institute of Architects (AIANY) as your guide.  This is the most comprehensive and elegant tour of the New York City skyline today. Learn more »

Private Charters

Host your own private event aboard a classic yacht in New York Harbor.  Office gatherings, client entertainment, weddings, birthdays for 2 to 120 guests across our fleet of 6 elegant USCG certified boats. Learn more »

Classically designed for a contemporary experience….

Join us on Yacht Kingston»

This is the most intimate sightseeing experience in NYC!

Urban Naturalist Tour»

Join us on our classic yacht for an Urban Naturalist Tour: Abandoned Islands of the East River at Sunset! (Limited Engagement: June 9 – July 21)

NYC Sailing Boat Rides»

Sail with us in NY Harbor for a Day Sail, City Lights Sail or Sunset sail!

Happy PRIDE month!»

Join us for our fundraising sail and cruise to support the Hetrick-Martin Institute!

Join us for 4th of July»

Celebrate 4th of July with us and enjoy the best seats in the house for the famous Macy’s Fireworks display!

SEE MORE TICKETED EVENTS

Classic Harbor Line: New York City’s Classic Style Charter Boat and Tour Boat Fleet

Dedicated to helping locals and visitors alike enjoy the unique wonders of New York City, Classic Harbor Line hopes for the privilege of escorting you on a relaxing, inspiring, and breathtaking NYC cruise through the waters we proudly call home. Our five classic yachts — the  Schooner  Adirondack  and the  Schooner  America 2.0  (our sailboats),  Luxury Yacht  Manhattan , Yacht  Manhattan II , Yacht  Kingston  and the Yacht Full Moon (our motorized yachts) are reminiscent of the classic boats that cruised the NYC waters in the past two centuries.

Whether buying tickets for one of our New York Harbor sightseeing boat tours to cruise out to see the Statue of Liberty or privately chartering one of our large sailboats or motor yachts for an office outing, you are sure to find yourself on a beautiful boat, surrounded by warm and friendly service, plying through the majestic New York City waterways.

We offer a wide range of ticketed sightseeing boat tours in New York City. Whether you are a fan of cruising on an elegant motor yacht to see the entire New York City skyline with comfort and speed, or if you are inclined to take a more adventurous escape on our swift, double-masted sailboats, you are sure to find a cruise that will suit you with service that treats you like royalty.

We offer a variety of cruises!

NYC Architecture Tours: We collaborate with the American Institute of Architects New York Chapter (AIANY), offering different Architecture sightseeing boat tours around the island of Manhattan. From the original AIANY Around Manhattan Architecture Tour to our brand-new NYC Climate Change Tour, you are sure to learn about the many iconic sights NYC has to offer. Enjoy one of these NYC Harbor cruises aboard our classic-style yachts. Learn More »

NYC Sunset Cruises: Watch the sun set behind the Statue of Liberty on one of our Sunset boat tours. Take in the sun's golden rays as they splash over the skyline of New York City, creating a wonderful collage of colors. These magical NYC sunset harbor tours are aboard our large sailing boats and motor yachts with plenty of space for passengers to move about along with premium customer service. Our NYC Sunset Cruises are relaxing, peaceful, and iconic! Learn More »

NYC Sightseeing Cruise When in NYC, you must do a sightseeing boat tour! Our yachts will bring you to see all of the major iconic sights New York Harbor has to offer. Crowd free, cruise with us in NY Harbor and grab some photos of the Statue of Liberty, One World Trade Center, Ellis Island, Governors Island, the Brooklyn Bridge, and more! Learn More »

NYC Fall Foliage Boat Tour Take to the water and join us for an epic Fall Foliage Boat Tour on the Hudson River. Cruise with us to the Grand Palisades for a sightseeing boat ride to take in the last leaves of fall. This is the perfect leaf-peeping cruise to enjoy a day on the water with friends and family. Don’t miss out on this Hudson River Fall Foliage boat cruise! Learn More »

NYC Holiday Cruises Everyone loves NYC in December! We host holiday shows and cozy sightseeing boat tours aboard our classic boats. Cruise with us on one of our heated yachts decked out in holiday décor and take in the NYC sites of the Statue of Liberty and the New York City skyline. Sit back and relax and enjoy the sounds of holiday jazz music, or grab the family and sing along with us on our Cocoa and Carols Cruise! Learn More »

Private Boat Parties Plan your next private NYC event and rent one of our boats! Our yachts are perfect for any occasion. Enjoy a private boat ride with us into NY Harbor as you and your guests take in the sites and sip on cocktails. Learn More »

Schooner America 2.0 »

Offering our most premium sailing experience in New York City, the Schooner America 2.0 is the newest, largest, and most elegant sailing vessel designed for our operation. Added to the fleet in 2010, America 2.0 offers the most exceptional day sailing one can find in New York Harbor. She is the fastest, most refined, and the most comfortable sailing vessel in our fleet and perfect to sail NYC!

The past meets the future aboard Classic Harbor Line’s Schooner America 2.0 . She is modeled after one of the most famous maritime icons of all time, the winner of the first “America’s Cup” of 1851, Schooner America . The “2.0” aspect of the vessel refers to the eco-friendly aspect of her cutting-edge construction by the designers at Scarano Boat Building, of Albany, New York . Rather than finding a diesel-consuming engine room below decks, you find a large battery bank providing electric propulsion. If you peeled away her hull, you find an extremely durable 3-layered composite of a light wood sandwiching an aluminum honeycomb instead a heavy, all wood vessel built from 100’s of trees. In place of a heavy wooden rig aloft, you find carbon-fiber masts, booms, and gaffs. Together, these strengthening and lightening components of construction help America 2.0 sail effortlessly and with less environmental impact.

From hoisting the sails, to serving beverages, to taking the time to answer your questions about the sights you are viewing, our crew aims for you to leave our boats feeling like you were always in great hands, and having made some new New York friends. We offer public trips for individuals, couples, families, and small groups, as well as private boat charters where you can customize the route, experience, and dining options for your guests.

The Yacht Manhattan & Manhattan II»

For power boat fans, the luxurious Yacht Manhattan & Manhattan II are the real gems amongst the New York Harbor boat tours . They are 1920s style, mahogany-trimmed “commuter” yachts that cruise with far fewer passengers than any other Manhattan sightseeing tour boat. Their ticketed harbor cruises average only about 20-100 guests per cruise. They have two regular routes on their ticketed cruises. One of the most unique is a 2.75 hour cruise that encircles the entire island of Manhattan, passing under 18 different bridges, and stopping briefly at the Statue of Liberty. The shorter 1.5 hour cruise is offered regularly during the afternoon, at sunset, and for stellar city lights cruises. This cruise on the Manhattan and Manhattan II captures all the key waterfront sites of the New York Harbor: the Statue of Liberty, Ellis Island, Battery Park, the Financial District Skyline, the Brooklyn Bridge, the East River and the United Nations Building, along with the numerous other landmarks of the Upper New York Harbor.

All of these cruises include a complimentary beverage from the teak and mahogany bar within the climate-controlled, sky-lit solarium. You can ride indoors or outdoors in absolute luxury and comfort year round. Aside from the yacht Manhattan’s regular ticketed schedule, you can also take advantage of many unique special event cruises. Each year there is a Mother’s Day Brunch Cruise, a Fourth of July Fireworks Cruise, a series of Fall Foliage boat rides up the Hudson River, a Wine Tasting Series, cruises offering specialty tours of New York Harbor, the only Around Manhattan Architecture Tour, and let us not forget a series of “Full Day Cruises” offering full day excursions to destinations on the Hudson River. Also, look for themed cruises to pop up throughout the year in the special events section of this home page.

Schooner Adirondack »

For the sailing enthusiast, a great way to take advantage of the New York Harbor sights is by sailing, aboard the elegant schooner: The Schooner Adirondack , our 80-foot wooden boat sails daily from Chelsea Piers May through November. She most commonly offers 2-hour day sails and sunset sails throughout the day with guaranteed passes by the Statue of Liberty. The Day Sails are perfect for families and guests interested in seeing the sites. These sails will always feature great views of the Lower Manhattan Skyline and Ellis Island, as well as complimentary beer, wine, Champagne and sodas. Wind and tide permitting, you may find yourself encircling Governor’s Island, or doing a short pass up the East River to get up close to the Brooklyn Bridge. Our Sunset Sail on the Adirondack is great for couples or co-workers looking to unwind after work. Another great NY Harbor sail for the romantic couple or a group of friends looking to have a fun night out on the water is the Schooner Adirondack’s City Lights Sail. This sail is truly magnificent and a local favorite. These sunset sails and city lights sails feature complimentary soda, water, beer, wine, and Champagne.

Yacht Kingston »

Yacht full moon », private charters ».

Private Boat Charters in New York City are an extremely popular choice for corporate entertainment or friends and family gatherings. Classic Harbor Line’s Private Events are perfect for 2 to 100 guests. The Boat Charters on the yacht Manhattan & Manhattan II can be accommodated with a wide range of services including full in-house catering, entertainment, and destination-oriented cruises. Please check out our Private Charters page for more information.

*****Tours not taxable, Food and Beverage served aboard are subject to NYS & NYC sales tax which is included in the cruise fares and beverage prices.

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Gift certificates, see our calendar of events, private charters.

Sail out into NY Harbor and impress your guests. Step aboard one of our classic vessels for a private charter. These yachts are perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

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Hawaii Sailing Adventures, LLC

Private Charters in Maui, Oahu, Lanai, Kauai

Private Hawaiian Catamaran, Sailing and Yacht Charters

It's time for the vacation of your dreams.

1/2 day, one-day, sunset, dinner, multi-day to multi-week inter-island vacation, and trip options are available.

Hawaii Sailing Adventures offers private boats, catamaran charters, and sailing trips on our luxury fleet. We provide charter options for Maui, Kaanapali , Kauai , Niihau, Lanai , Molokai , Honolulu, Waikiki, Oahu , Kaneohe Bay, and The Big Island.   Snorkel, whale watch and visit Napali Coast, Kaanapali & Kohala Coast, exploring the beautiful "unknown" Hawaii through our one of our luxury boat trips.

Contact us  to learn more about booking a private catamaran or boat charter where you'll create a memorable adventure for your family and friends. Enjoy extraordinary encounters with whales, dolphins, and sea turtles, swim and snorkel in tropical island waters and have the best sailing experience in your lifetime!

Explore Our Fleet

Custom 49 catamaran

Fountaine Pajot Bahia 46

Fountaine Pajot Helia 44

Excess 12 – 39’

42 Catalina MK 11

Beneteau Oceanis 48

Nautor Swan 46

Beneteau 42

Beneteau Oceanis 41

Beneteau 393

Beneteau 39

Ferretti 69

Chesapeake Bay 36

Ready to find out more.

Get information on prices, itineraries, private daily or weekly charters & tours in Hawaii.

Napali Coast, "The Forbidden Island", North Shore Molokai, Kanaapali, Manele Bay

Niihau, Kalalau Valley, lagoon, reefs and beaches, sea cliffs, waterfalls, snorkel, scuba, swim, sunbathe, kayak, paddleboard, surf, windsurf, fish, and dine ashore. Stay in the harbor as a pleasant, charming, quiet, relaxing home base with all the cooking and sleeping amenities, a more creative environment than a hotel or house, and explore on-island activities on a week or two sailing charter. Relax, work the sails, whale watch, extended inter-island trips, short sailing tours, sunset sail, and dinner cruise. Feel what it is like to offshore cruise in the most dramatically beautiful settings in the world. Our crewed sailing and luxury yacht charters and boat tour prices include skipper, food, fuel, gear, other vessel costs, Sail Blue Hawaii, and much more.

What our customers say...

"Thank you so much! We loved the day and the memories will be cherished. We hope to do it again some day."

The Ferrier Family

A dream wedding in hawaii.

Ask us about our tropical, romantic wedding and honeymoon packages. Then, let us arrange your marriage ceremony aboard your private yacht.

Catamaran and Monohull sailboats to; Maui , Lahaina, Molokai , Lanai , Oahu , Honolulu, Kauai , Niihau, Big Island Hawaii .

Book Now your 5-night Sailing Adventure through the San Blas Islands from $660 USD!

Can’t fit the full tour? Book Now your 3-night San Blas Charter Vacation from $495 USD!

Welcome to our salty world Are you ready to discover the San Blas Islands? Join our sailing trip and let yourself be carried away by adventure! Contact Us Join us on this cross-continental passage between Americas Sail from Colombia to Panama and vice versa, crossing through the paradise that is the Caribbean. Contact Us Be salty, Live Tasty! Explore the beauty of the San Blas archipelago on our fleet of sailboats and catamarans. Contact Us Reserve your spot in paradise now! Book your sailboat adventure with just a 10% deposit. Contact Us Sail, Explore, create memories Experience life on board and enjoy the adventure of navigation while feeling the freedom that the sea provides with our licensed and experienced crew. Contact Us Welcome to our salty world

Are you ready to discover the San Blas Islands? Join our sailing trip and let yourself be carried away by adventure!

Salty travels, spicy memories

Explore the beauty of the San Blas archipelago on our fleet of sailboats and catamarans.

Save your place to paradise

Book your sailboat adventure with just a 10% deposit.

Join us on this cross-continental passage between Americas

Sail from Colombia to Panama and vice versa, crossing through the paradise that is the Caribbean.

Sail, Explore, create memories

Experience life on board and enjoy the adventure of navigation while feeling the freedom that the sea provides with our licensed and experienced crew .

Colombia & Panama

Embark on an extraordinary sailing adventure between Colombia to Panama or vice versa with our 5-day intercontinental sailing cruise. It includes 25-50 hours of open sea crossing and 3 days of blissful exploration of the paradise that is San Blas. This tour covers over 210 nautical miles of thrilling navigation. Join fellow adventurers, immerse yourself in new cultures, and unleash your inner pirate with our ultimate sailing experience.

Charters in San Blas

Discover the beauty of San Blas! Join our three-night shared charters just around San Blas departing from Panama City and returning to Panama City on the morning of the fourth day. With our 3-night package, you’ll have everything you need to live an unforgettable experience, from delicious meals to exciting snorkeling, volleyball & bonfires activities.

Why book with us?

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There´s still time to join us we have very few spots remaining on our san blas trips so there´s no time to delay..

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Updates on Current Sailings

High water (european rivers) – as of june 3, 2024.

Currently, sections of the Rhine, Main and Danube rivers are experiencing high water levels. To varying degrees, these conditions may affect select itineraries. Our Switzerland-based nautical team is continually monitoring the situation and will make any necessary adjustments to accommodate the conditions. Guests and their Travel Advisors will continue to be notified directly if we think that their itinerary might be impacted. Viking has two key advantages with regard to handling water level disruptions. First, we own and operate our ships. We have a Switzerland-based nautical team and a network of local partners and authorities that are focused on monitoring and adapting to current water levels to ensure our guests experience the least possible disruption. Second, we strategically launch sister ships on the same itinerary, but sailing in opposite directions. In the event of high (or low) water, this tactic allows us to implement a ship swap that is typically seamless for guests – both they and their luggage are able to be transferred to their exact, identical stateroom on a sister ship that was purposefully sailing on the other half of the river in preparation for such a disruption. These advantages allow us to minimize the impact that water levels can have on itinerary, which means our guests are better able to focus on enjoying themselves and having a great journey, rather than worrying about potential changes or cancellations.

For Further Assistance

If you have any questions or need further information please contact Reservations at 1-877-523-0579 or email [email protected] , Monday – Friday, 6:00 AM – 6:00 PM; Saturday and Sunday, 7:30 AM – 4:00 PM, PT.

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Sailing cruises

Is there a better feeling than clipping through the waves with the sun on your face? Or watching stars come out over the Aegean Sea with a glass of champagne?

Sailing holidays don’t have to be an intimidating tangle of ropes, nautical jargon, and sea monsters – not with Intrepid. Whether you’re a fresh-faced novice or an old salt with callouses on both hands, we’ve got a sailing trip to suit you. Be as involved as you like. Help navigate, tack, and steer; or simply kick back on deck with a copy of Moby Dick and let the world float by. These are small groups on small boats, but with big adventures.

Our skippers have years of experience sailing the high seas. There’s no one better to show you the ropes (literally).

These sailing vacations aren’t confined to the ocean blue. There’s plenty of time scheduled on land to see the sights and check out the local culture.

Our yachts are well looked after and regularly maintained and on day one, the captain will also conduct a safety demonstration.

If you'd like to pick up some sailing skills, your skipper can show you how. If not, just relax, kick back on deck and soak up some ocean breezes.

We strive to use travel as a force for good. That’s why we choose to give back to the communities we visit, carbon offset all our trips and take our social and environmental responsibilities seriously. We’ve been officially certified as the world’s largest travel B Corp, which means when you choose Intrepid Travel, you can rest assured you’re travelling to improve the planet.

From the famous landscapes of Phang Nga Bay to the pristine beaches of Koh Phi Phi (and all of the remarkable islands in between), a sailing adventure through southern  Thailand  promises to produce some of your favourite travel memories ever. Relax on golden sand, take a dip in sparkling turquoise waters, and cast your eyes upon natural wonders you’ve only ever seen photos of. 

There are some destinations in this world that were made for sailing and the  Galapagos Islands  is one of them. Whether you want to spend your time spotting the islands’ diverse array of wildlife (think spiky marine iguanas and giant turtles) or simply relax on the boat with a drink in hand as the Pacific Ocean goes by, a boat tour around the Galapagos is sure to be one for the highlight reel. 

Sailing your way down the  Italian  coast is guaranteed to be a unique adventure you’ll never forget thanks to a variety of stops featuring pastel villages clinging onto rugged cliffsides, scattered ancient ruins from a lost empire, and tantalisingly blue waters you want to get lost in. From wandering through olive groves to laying out on pebbled beaches, cruise the sparkling Mediterranean at your leisure. 

On a trip to Europe,  Croatia  is a must-see but when figuring out how best to explore this Mediterranean country, sailing is the way to go. Whether you want to wander through medieval towns, lose yourself in sparkling blue waters, explore unvisited treasures or indulge in this epic country’s traditional cuisine, you’ll be in utter paradise from the minute to step foot onto your own private yacht – all aboard! 

When it comes to sailing in  Europe , we like to go classic. A single-hulled, 50-foot yacht gives you a taste of traditional Mediterranean sailing, not to mention it looks pretty spiffy in pictures too. A typical Intrepid vessel may come with three twin/double cabins, as well as a couple of single berths. You’ll have a recreation lounge, kitchen, three shared bathrooms and plenty of deck space for lazing around and looking fabulous.

When it comes to sailing in  Asia , catamarans are the way to go. They’re smooth, comfortable, and nimble enough to reach those out-of-the-way cays and little island inlets. The twin hull means there’s plenty of space to stretch out –perfect for those balmy evenings and lazy afternoons. Most of the catamarans in our fleet have four twin/double cabins, three shared bathrooms, a galley (that’s nautical talk for kitchen) and a small living area. There’s even kayaks and paddleboards for those that want to get a little active (and bean bags on deck for those that don’t!)

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Sail Greece: Santorini to Mykonos

Sail Italy: Procida to Amalfi

Greece Sailing Adventure: Cyclades Islands

Do I have to help sail the boat?

You don’t have to lift a finger if you don’t want to (unless you need to turn the page of your novel or eat a grape). But if you’d like to learn the ropes, that’s fine too. Your expert skipper can teach you everything you’d like to know – from tying knots to unfurling the sails.

How much time is spent off the boat?

There’s about a 30/70 split between land-based and water-based activities on our Asia sailing trips. In Europe this is closer to 50/50 however some evenings will be spent in port or a marina. Much of this depends on the weather conditions. There are usually at least a few hours each day spent exploring ports, trekking the surrounding areas or relaxing on beaches. Of course, depending on location, there will always be the chance to wine and dine at the local hot spots. 

What will my fellow travellers be like?

We have travellers of all ages and nationalities travelling with us. Approximately 60% of our travellers are single travellers, followed by a mix of friends travelling and couples. The minimum age of travellers on our trips is 18, or 15 if accompanied by an adult. We don’t have a maximum age as we believe those choosing a sailing adventure are like-minded regardless of age.

Who decides the rooming configuration?

Your skipper will allocate rooms on arrival to the boat. Single travelers will be paired up with another passenger of the same sex, and this may mean sharing a double mattress or twin mattresses side by side.

What are the sleeping arrangements like?

This is our most common question. People are often hesitant about the idea of sharing a double mattress with another traveller of the same sex. Sailing boats tend to be very compact (and we use real sailing boats), and the close-quarters nature of this travel is part of the adventure.

Sleeping quarters are designed to utilise the minimum amount of space in order to keep the communal areas as big as possible. In practice, lots of travellers end up sleeping out on deck under the stars, as it’s warm and there’s no air conditioning on a sailing boat.

Our boats have a mix of double, twin (two separate beds or two separate mattresses side by side), bunks, triple and quad cabins. Each trip will have further information about the sleeping arrangements in the Essential Trip Information.

Can I get a cabin to myself?

Yes. Single supplements are available on all trips subject to availability. A single supplement is normally twice the regular price, however where trips have inclusions such as meals there is a slight reduction in the supplement price. If you are interested in having a single supplement please contact us to check availability and price.

Do the cabins have ensuites?

On many boats bathroom facilities are shared, however some boats have ensuites in each cabin that allow two people to share one bathroom. Our monohull yachts in Europe will have no more than two cabins sharing a bathroom. Most of our catamarans have four cabins and four bathrooms, however these bathrooms are shared between travellers and crew. Check the Essential Trip Information of your trip for more specific details about your boat. Fresh and hot water is available for showers, and toilets are either electronic or hand pump.

Will I get seasick?

Seasickness comes in a variety of forms. Common symptoms include fatigue, uneasiness, dizziness, and headaches. The majority of these symptoms usually subside after taking some time to adjust (usually a few hours to a day). Paracetamol tablets can help ease the transition. Heavy seasickness, characterised by vomiting, is uncommon, and it can be treated using medication. There are also a number of other self-management techniques you can try – such as sitting out in the fresh air, drinking ginger tea or watching the horizon. 

For more information about beating seasickness, click  here . 

What will I eat?

Our Thailand sailing trips all feature an onboard chef who will prepare three delicious meals each day, plus snacks. In Europe, we operate with a trip kitty* that everyone contributes to. This is because there’s so much great local produce to taste in each place that it makes a lot of sense to buy food at each stop! This kitty will cover some of your food and beverage costs. On all our trips there will be an opportunity to enjoy a meal at a local port – we’ll be able to show you where all the good tavernas are. Please check your Essential Trip Information for more specific details.

*See below for information about what a kitty is

What about alcoholic drinks?

You are welcome to drink on board - in fact, nothing enhances a sunset more than a gin and tonic – however alcohol is BYO (bring your own). So make sure you buy what you need before departure. Some of our boats have alcoholic drinks on board that are available for purchase at local bar prices. Drinking water is free of charge.

How much luggage should I take?

Due to the compact size of the boats and the sometimes rocky nature of a sailing trip, it is advisable that you bring fabric/canvas luggage. It’s a good idea to pack light as there will usually be a gap between the boat and pier. While the skipper or a fellow traveller can give you a helping hand, you’ll need to be able to lift your bag onto the boat.

What should I pack?

Sailing trips are a little different to regular group tours. There’s a finite amount of space on the boat, so it’s best to leave the grand piano, pet llama and foldout four-person mattress at home. Same goes for bulky suitcases, ten pairs of shoes and the surfboard.

This isn’t designed to be a comprehensive packing list, but it’ll get you thinking like a real sailor.   

A medium-sized fabric bag that can be flattened or stored easily

A small day pack for shore excursions

Some flip flops or deck shoes that can get wet

Sunscreen, sunglasses and a hat

Seasickness tablets (just in case)

Swimmers (don’t worry about the snorkel and fins – we provide those)

Waterproof camera (for those sweet underwater shots)

A light weatherproof jacket (just in case of high seas or seasonal showers)

For a more detailed packing list please refer to the Essential Trip Information of your trip. 

What are the arrival and departure times?

These will vary from trip to trip – be sure to check your Essential Trip Information for more specific details. Some sailing trips will head out to sea on the afternoon of the first day. Others will remain in port overnight, however we still ask that you join the trip at the requested time as the skipper will need to deliver a welcome and safety briefing. On our Europe trips the skipper will organise a visit to the supermarket after the meeting to buy provisions for the trip. All travellers will have an input into the provisions, which will be purchased from the kitty*.

Please note that due to sailing being a heavily weather-dependent activity, sometimes itineraries may need to change. We recommend allowing an additional night at the beginning and end of the trip to ensure nobody misses any onward flights.

*see ‘What is a kitty’ for more information.

What is a kitty?

A kitty is a fund or pool of money that all travellers can choose to contribute to at the beginning of a trip. It’s not compulsory however we’ve found pooling the group's money in one place makes it easier to arrange non-included group meals and tips where necessary. You'll usually eat most breakfasts and some lunches and dinners onboard the boat, so it's best to buy supplies from a nearby supermarket or grocery store at the beginning of each trip. For meals off the boat, our skippers will suggest locally-run restaurants that specialise in local produce and delicacies.  

What is the maximum group size?

The maximum passenger capacity on our yachts changes depending on which country you are sailing. Here’s a quick breakdown, but you can always find more specific details in the Essential Trip Information of each trip.

Greece: 8/11 

Croatia: 8 

Montenegro: 8 

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From business suits to swimming shorts: the life of a skipper in the Greek Islands

Which Greek Island is right for you?

Myth conceptions: 5 Greek Islands that mythology lovers shouldn’t miss

How to do the French Riviera on a budget

How a night on a Turkish boat taught me the real meaning of Intrepid

Another World Adventures

Sail across the atlantic ocean – join transatlantic sailing voyages, it’s every adventure seeker’s dream to sail across the atlantic ocean..

And we’ve helped hundreds of sailors – new and experienced – to turn that dream into reality.

Find transatlantic voyages here where you book a berth or cabin and join join as hands on guest crew on planned journeys and rallies like the ARC, or if you’d like to charter a whole boat then get in touch .

We work with a network of many incredible boats from luxury yachts, performance racers to historic traditional tall ships.

If you have the ambition to sail across the Atlantic Ocean, whether you’re a beginner or pro sailor, there are exciting options for you on board hands-on sailing vessels. Join yachts or tall ships as guest voyage crew and learn incredible new skills, as you pull together as a team to harness the wind and reach a new continent. It’s a sustainable long-distance travel option that is all about embracing the journey.

Complete our short form to let us know your Atlantic ambitions and we’ll be in touch with exciting options.

Which direction?

A big first consideration for many when planning their transatlantic is which direction to sail – east or westbound and if you’re fixed on that it will determine when you’ll go.

Westbound: Europe to the Americas & Caribbean tend to depart with the trade winds in between October-December.

Eastbound: Caribbean & Americas to Europe tend to sail between March – June (April & May most commonly).

Northbound : South Africa to Europe voyages tend to depart between April-June

How experienced are you?

Our crews are a mix of sailing abilities.

Some enter races and you’d be expected to know what you’re doing, others teach you everything you need to know on the go. You’d just need to join in with a ‘can do’ and ‘here to learn’ attitude and the professional crew will help with the rest!

Want to join a crew for a fixed departure?

We have limited spaces available on organised voyages – these trips are very popular and often book out far in advance.

First step: Explore the listings and make an enquiry on the voyages you’re interested in. You’ll receive more information by email right away and if you asked any questions we’ll get back to those as quickly as possible. In the info you receive is an intro to the skipper or crew office for the boat so you can go ahead and book with them directly if it’s the right fit. These berth options are perfect for solo travellers or couples/pairs/small groups of friends.

Or book a private charter?

Bespoke voyages are organised separately, so reach out to us through the contact form or by email for more details on these.

Or get in  touch using the contact form above so we can help you make this trip dream a crossing to remember!

Voyages to sail across the Atlantic 2024 / 2025 and beyond

2024 east bound.

• Sail from USA to Scotland via Newfoundland 2024 Clipper 60
• Sail from Caribbean (Tortola, BVI) to Azores, to UK on a Celestial Navigation voyage  Clipper 60
• Beneteau 40 or Harmony 52 yachts sailing Caribbean to UK
• Sail British Virgin Islands > Azores > UK May/June  2024 – tall ship
• Sail Caribbean to France  on a Challenge 67
• Sail Cape to Cape – Chile to South Africa via Antarctica, South Georgia and Tristan de Cuna – tall ship
• Sail New York USA to Lorient France in June 2024

2024 Westbound

• ARC 2024 Canary Islands to St Lucia on a Beneteau 40 or Harmony 52
• Challenge 72 ARC entry 2024 to St Lucia
• Luxury 54ft Catamaran sailing Canary Islands to Martinique
• Tall ship adventure sailing Tenerife to Falkland Islands

2025  Eastbound

• Sail West Indies to France March 2025
• Sail Argentina to Namibia via Antarctica tall ship Feb/March 2025
• Sail Caribbean to Rotterdam tall ship March 2025
• DARWIN200 South Atlantic Falkland Islands to Cape Town via South Georgia & Tristan da Cunha Feb-April 2025
• Beneteau 40 or Harmony 52 yachts sailing Caribbean to UK March/April 2025
• Celestial Navigation voyage sail Caribbean Antigua to UK Clipper 60 March-April 2025
• Sail NYC to Lorient France June 2025 

2025  Westbound

• January 2025 Atlantic Circuit Sail Lisbon to Suriname tall ship
• January 2025 RORC transatlantic race
• Sail Lorient France to NYC USA in May 2025
• We expect to have several tall ships and yachts making the crossing to the Americas with and independent of the ARC so email us if you have any questions!!

Check all Atlantic ocean crossings here or email Larissa on [email protected]

Want to sail, but not sure about a transatlantic voyage?  We have options for everyone. Check out:

• All sailing adventure holidays
• Ocean adventures
• Tall ship adventures

Tall Ship vs Yacht?

Finding the right boat for your journey is a important part of your planning, not just the route. Each boat has it’s own character, style and charm – and personality! And the on board experience varies hugely depending on the reason for the boat sailing – is it taking part in a race? Is it an ocean cruise slow travel experience? And so on. The degree to which you’ll be mustered to help with the sailing and life on board also varies so whether you’re keen to join a 50ft yacht or a full size tall ship we’re happy to talk you through the options to find the best fit.

What is it like on Board a Transatlantic Voyage?

Experience navigation, planning and life on board with your fellow crew who will be a mix of ages and from all walks of life.

There’s rarely an upper age limit on the voyages although some of the tall ships have more recently set a limit of 73 for their offshore voyages (please ask for details). Decisions on whether someone is a suitable crew are made on a case-by-case basis by the crew office for each vessel but the key requirement is good health and an enthusiasm to get involved.

Solo Travel Sail Across the Atlantic Ocean

We met as two solo travellers on board a transatlantic voyage, so we understand the opportunities and challenges of solo travel on long journeys at sea.

It was a life-changing experience for us and Another World Adventures wouldn’t exist without that solo travel experience.

The really good news for solo travellers is that when it comes to ocean sailing trips around 80% of the people joining are doing so on their own – so if all of your mates look at you like you’ve grown two heads when you tell them your Grand Plan then don’t worry, you’ll be in great company with the friends you’ll make on board.

Sail with Friends Across the Atlantic Ocean

As well as being an amazing experience for those travelling solo, transatlantic sailing with friends can bond you for a lifetime.

As experienced adventure travel planners, we can connect you with a reliable and responsible vessel that you can join together to make the crossing. Heck, we’ve even known honeymooners celebrate their marriage with an ocean crossing.

All that’s needed is an adventurous mindset to sail across the Atlantic.

Private Charter to Sail Across the Atlantic Ocean

If you are looking for a more personalised experience, we can coordinate bespoke voyages for individuals, groups and companies.

Let us help you find and charter a private vessel for a journey across the Atlantic Ocean.

Whether it’s a bonding experience with friends, a brand contest or marketing effort, or a chance to achieve a life-long dream, we can help you navigate the best vessel choices  whether you’re 4 or 40 sailors.

Do I Need Prior Sailing Experience to Sail Across the Atlantic Ocean?

You do not always need much prior sailing experience to take on the challenge of a transatlantic sail although it is advised to ensure you and your fellow crew get the most out of the experience. Afterall, this is a really big experience to go into without knowing if it’s your cup-of-tea. For many of the boats we work with, especially the tall ships, sailing experience is not compulsory. Instead, the vessel crew will give you hands-on experience and training along the way – both on expedition sail yachts and tall ships. 

If you’re looking for an experience on a smaller vessel, you might need to have or get some sailing experience or qualifications beforehand. For example, some of the race boats or smaller yachts (60ft) require RYA Day Skipper or equivalent, so speak to us if you’d like more information. A few of the passages are even qualifiers for Yachtmaster Ocean mile makers, so if you have bigger ambitions for your sailing, please reach out to ask about that and about Watch Leader roles, too.

Be Inspired to Sail Across the Atlantic Ocean by our Previous Atlantic Sailing Voyages

Below are some voyages from the past which we’ve left up to give you an idea about routes to consider. If there’s a route you love the sound of but it’s not in the current schedule then just drop us a line to find out more. With so many changes to the sailing schedule for ocean journeys there’s a chance it’s in the planning stages, just not yet announced..!

If you’re not sure of the best option for you, speak to us about your plans and dreams for this great adventure,  so we can advise you on the best voyage route and crew to join.

Transatlantic Route inspiration

Past voyages have included

• South Africa to Canada 2019 – January – May 2019 – This was the final leg in a circumnavigation that set off in spring 2018 on board a unique sail training tall ship. Solo travellers were invited to join the crew of this remarkable vessel for the voyage of a lifetime. Unusually for the ocean crossings this voyage included lots of stops along the way.
• Sail Cape to Cape via Antarctica on a traditional tall ship from South America to South Africa.
• Sail Cape Verde to Cuba
• Sail Falkland Islands to South Africa 2018
• Sail Bermuda to the UK on a traditional tall ship
• Sail USA to the UK via the Azores on a Clipper 60 yacht
• Sail Azores to the UK on a tall ship
• Sail Europe to South America on a Dutch tall ship
• Sail USA > EUROPE (Florida to The Netherlands via Bermuda and Azores)
• Sail Antigua and Barbuda to the United Kingdom
• Sail South Africa to Norway via Azores, Ascension Island and St Helena
• ARC – Atlantic Rally for Cruisers Canary Islands to St Lucia (via Cape Verde)

If you see a trip listed here but not on the Atlantic sailing trip page , please contact us to discuss your options. We are constantly updating this list so get in touch if you don’t see a route that works for you and we’ll see what is possible.

Atlantic Crossing with ARC Rally – Gran Canaria – Saint Lucia

Cross the Atlantic as part of the ARC Rally on this bucket list adventure from Gran Canaria to Saint Lucia

Sail Around the World via Cape Horn Square-Rigged Tall Ship

Join the crew of a square-rigged tall ship to sail around the world by way of Cape Horn

Sail Transatlantic New York City USA to Lorient, France

Embark as a teammate in a transatlantic voyage on a Challenge 67 from USA to France

Sail Transatlantic Argentina to Namibia 2025

A TRUE epic - sail a traditional tall ship from South America to Southern Africa via Antarctica

Sail Cape to Cape Chile to South Africa via Antarctica, South Georgia and Tristan da Cuna 2024

Join a Cape to Cape sailing voyage via Antarctica, South Georgia & Tristan da Cuna on a tall ship

Sail ARC Atlantic Rally 2023

Join the famous Westbound Atlantic Rally crossing on a fantastic sailing cruiser.

Sail Transatlantic Lorient to New York City

Embark as a teammate in a transatlantic voyage on a Challenge 67 from France to USA

Sail ARC Transatlantic 2024

Embark as a teammate in a transatlantic voyage on a Challenge 67 during the ARC 2024!

Atlantic Circuit Sailing Adventure

An Atlantic Circuit sailing adventure including two transatlantic crossings and some unusual port stops

Sail Transatlantic Westbound Luxury Catamaran 2024

Embark on the voyage of a lifetime sailing from Gran Canaria to Martinique on an exceptional 54ft catamaran

Sail ARC 2024 Transatlantic

The voyage of a lifetime to sail across the Atlantic Ocean with a crew in the ARC 2024.

Transatlantic Eastbound Sail Antigua – UK 2024

Join a crew to sail back across the Atlantic Ocean from Antigua to the UK

Sail Spain to Canary Islands

Offshore sailing between Malaga and Lanzarote, Canary Islands on a fantastic sailing cruiser.

Sail Around the World As Crew on a Square Rigger

Become crew on an authentic working sailing ship on a global circumnavigation. 20+ ports, 30000 nautical miles

Transatlantic Sailing Tenerife to Falkland Islands

Adventure sailing Tenerife to Falkland Islands from the North Atlantic into the South Atlantic across equator

Atlantic Crossing Cape Verde to Fernando de Noronha Brazil DARWIN200 Leg 3

Crossing the Atlantic Ocean from Cape Verde to Brazil Fernando de Noronha.

Sail Caribbean to UK via Azores Tall Ship 2024

Hands on sailing a classic brigatine across the North Atlantic from Caribbean to Azores to the UK in May '24

Sail Across the Atlantic Ocean – Cape Town to Montevideo

Experience life at sea as you sail across the Atlantic Ocean on a 100 year old traditional tall ship.

Celestial Navigation Transatlantic Eastbound 2025

Navigate by the stars as you sail across the Atlantic Ocean eastbound from Antigua to UK

Join a RORC Transatlantic Race Crew 2025

Embark as a teammate racing on the RORC Transatlantic Race where you are the crew in this legendary event

Hi I’m Larissa, Founder of Another World Adventures. Welcome! If you’re planning an adventure you’re in the right place. Get ready to discover epic travel inspo and a collection of hand-picked trips from my trusted network of experienced adventure experts. Think unusual destinations, expeditions, slow, solo and sustainable travel and epic journeys on land and at sea! Ever got a question? Just get in touch, I answer every enquiry myself. Enjoy!

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Sailing Holidays

The Earth is two-thirds water, yet we spend most of our life on land. So cast off, take the plunge and discover the life-changing freedom of a sailing holiday. VentureSail offers 400+ adventures to amazing destinations on unusual boats run by passionate crews. Get hands-on and learn the ropes, or relax on deck and enjoy the journey wherever it takes you. There’s a huge choice across the fleet, from private ensuite cabins on luxury yachts to shared quarters on a tall ship. So much of the world is waiting to be explored; discover it under sail.

Featured Sailing Holidays

Sailing & Island Hopping in Cape Verde

• 10 January 2025, 12 days
• Vessel: Morgenster
• Port: Cape Verde
• Board type: Full Board

Sailing in Scotland with Grayhound

• 16 August 2024, 5 days
• Vessel: Grayhound
• Port: Oban, Scotland

Sailing & Exploring in the Hebrides

• 27 May 2025, 7 days
• Vessel: Steady

Family Sailing The Indonesian Wonders; Whale Sharks, Corals & Dragons

• 30 July 2024, 9 days
• Vessel: Ombak Putih
• Port: Komodo, Indonesia

Sailing in Scotland; Mull & the Small Isles

• 17 May 2025, 7 days
• Vessel: Bessie Ellen

Tallship Sailing from Scotland to Cornwall

• 5 August 2024, 10 days
• Vessel: Blue Clipper
• Port: Scotland/Cornwall

Private Charter Island Hopping in the Bahamas

• 19 March 2025, 8 days
• Vessel: Bonnie Lynn
• Port: The Bahamas

Expedition Sailing in Svalbard

• 20 July 2024, 8 days
• Vessel: Valiente
• Port: Svalbard, Norway

Sailing the Indonesian Wonders; Whale Sharks, Dragons & Coral Reefs

• Vessel: Katharina

Luxury Island Hopping in Croatia

• 15 June 2024, 8 days
• Vessel: Kairós
• Port: Croatia

Hands-on Sailing in Denmark; Aalborg to Svendborg

• 16 September 2024, 5 days
• Vessel: Aron of Svendborg
• Port: Denmark

Luxury Sailing in Greece; Zante & Kefalonia

• 7 June 2025, 8 days
• Port: Greece

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Our range of vessels enables us to offer several destinations all over the world. Which sailing holiday will you choose?

Take a look at our unique fleet. From classic boats to luxury yachts and expedition vessels, there is no shortage of choice for your sailing holiday.

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Route Planner

Plan your sailing route.

Planning your sailing route is an important part of preparing for a sailing trip. There are various reasons why it is recommended to plan your route in advance. To begin with, choosing your sailing itinerary ensures your safety while out at sea. By researching and planning your route in advance, you may discover hazards such as rocks or shallow waters and avoid them, thereby keeping yourself and your passengers safe. Furthermore, choosing your route before your sailing trip permits you to visit all places you want and to make the most of your time aboard . This is particularly important if you are on a tight schedule or on a short trip.

Sailing Route Planner Tutorial

With our interactive boat route planner, you can plan your sailing trip down to the smallest detail. Our route planner tool allows you to choose your starting point and draw your desired sailing route. Once you're finished, the distance will be automatically calculated, and you can choose to have the sailing route sent to your email. Additionally, the boat route planner displays the coordinates of your starting and finishing points, so you can always know your exact location using your onboard instruments. Our boat route planner is the perfect tool to ensure the safety of your sailing trip. 

Click on the video on the right and see an example of how to plan your own sailing route.

Don't lose your route , receive it on your e-mail.

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7 Day Sailing Tours & Trips

See the best 7 day sailing tours. There are 105 adventures, in as many as 17 different destinations, including Croatia and Jordan.

7 Day sailing tours with 216 reviews

Sailing Explorer Christmas & New Year +1

Sailing Thailand - Phuket to Phuket

"I didn't expect perfection, so I was surprised by it. Next time I won't expect perfection, and see what happens." Lawrence, traveled in December 2022

Sailing Thailand - Phuket to Ko Phi Phi

"He balanced the expectations and desires of a diverse group to ensure a fulfilling itinerary." Mary, traveled in April 2019

Sailing Boat Gulet Explorer

4-day Split to Dubrovnik One-way Cruise - Classic Plus above-deck, 18-35s

"Great trip, crew were amazing! Will definitely go again" Keith, traveled in August 2018

5-day Dubrovnik to Split one-way cruise - Classic Plus above-deck, 18-35s

"Amazing and beyond my expectations..." Dalma, traveled in July 2019

Phuket Sailing Adventure

"Amazing boat, staff and food! Visited beautiful places!" TAMARA, traveled in December 2018

Sailing Christmas & New Year

Sail Phuket to Ko Phi Phi

"The secluded beaches and surreal scenery were the best. Waking up on the deck to the gorgeous sunset and the feeling of being one with nature is something I will never forget." Fisayo, traveled in May 2014

Sailing Family Historical Christmas & New Year +1

From Luxor: 5-Day Luxury Nile Cruise to Aswan with Balloon

"The cruise was really fantastic. We enjoyed every bit of the trip, the temples, the cruise ship (which included a pool on the roof)." Mo, traveled in April 2024

Sailing Yoga Health, Spa & Wellness +1

1 week of Sailing & Yoga Practice + SUP usage in the SARONIC ISLANDS

"Wonderful and relaxing experience" ling, traveled in September 2019

Croatia Explorer: Superior Catamaran from Split

"The boat is well appointed, including the cabins. There was plenty of food and drink included and we were able to take our own aboard." Susan, traveled in May 2019

Sailing Family

Highlights Of Quito and Galapagos Islands

"The experience was great. Nearly everyone who assisted us was very helpful." Mary, traveled in March 2023

Sailing Family Explorer Hiking & Trekking +1

Walking with the Gods

"The boat was nice and clean. The itinerary was well planned so the trip was really relaxing and enjoyable." Alexis, traveled in June 2019

Blue Escape in Turkey: 5 Days Sailing Tour from Gocek to Fethiye

"Great experience lovely food lovely people" Eva, traveled in August 2023

4 Days Blue Escape from Fethiye to Gocek

"The trip offered a beautiful escape to the breathtaking coves around the bay of Fethiye with plenty of opportunities for swimming." Livia, traveled in June 2023

Sailing Active Family Sport +1

Dubrovnik Adventure Sailing Break with Huck Finn Catamaran

"Simpa planned our trip so that we were able to hit the majority of the sites. Andrea was instrumental in the success of the entire trip!!!" Nicole, traveled in September 2019

Sailing Explorer

Ionian Discovery

"Great communication and information about where we were & where we were going as well as recommendations." Heather, traveled in August 2023

Reviews of 7 day Sailing Tours

Everything went as planned. My guide Fon was very knowledgeable & accommodating.

Fantastic trip. Don’t hesitate to book. We did the 4 days one because I was nervous about being stuck on a boat for four days but they planned great stops and activities and I never once felt bored or like I want to get off the boat. The trip went around the most magnificent scenery and the food was amazing. Would do it again in a heart beat.

Nice boat but most important nice boat crew. A great atmosphere and service. We spent 4 very nice days. Breakfast and lunch were included and the cook was really talented. Unlimited water was available as well as fruit. It was a party boat but there was the flexibility to do whatever you wanted when in port.

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Passing Thru Travel

15 Best Sailing Destinations: A Guide To Sailing Schools for Beginners

Posted: March 8, 2024 | Last updated: March 8, 2024

Embarking on the journey of learning to sail opens up a world of nautical adventure and discovery. This guide is tailored for those beginning their sailing voyage, highlighting the world’s top destinations renowned for their sailing schools and beginner-friendly waters. From New England’s breezy coasts to the Mediterranean’s serene waters, each destination offers a unique setting for learning the art of sailing. Whether you seek comprehensive courses or a casual introduction to sailing, these locales provide the perfect starting point for your nautical adventures.

1. Annapolis, Maryland, USA

Annapolis is known as America’s Sailing Capital and offers an ideal environment for novice sailors. The Chesapeake Bay’s calm waters and steady winds create perfect conditions for learning. Sailing schools in Annapolis provide a range of courses, from basic skills to advanced navigation. The city’s rich maritime history and vibrant sailing community enhance the learning experience.

Insider’s Tip: Enroll in a course that includes navigation of the Chesapeake Bay to gain practical experience.

When to Travel: Spring to early fall for ideal sailing conditions.

How to Get There: Fly into Baltimore-Washington International Airport and drive to Annapolis.

2. Auckland, New Zealand

Auckland, known as the “City of Sails,” is a premier destination for learning to sail. Its numerous harbors and islands provide diverse sailing experiences. Sailing schools in Auckland cater to all levels, offering courses in a city surrounded by stunning natural beauty.

Insider’s Tip: Choose a school that offers trips to nearby islands for a varied sailing experience.

When to Travel: October to April for warm weather and favorable sailing conditions.

How to Get There: Fly directly into Auckland International Airport.

3. Corfu, Greece

The island of Corfu in the Ionian Sea is a picturesque locale for sailing beginners. Its clear, calm waters and gentle winds make it an ideal place to learn. Sailing schools in Corfu often combine lessons with exploration of the island’s stunning coastlines and beaches.

Insider’s Tip: Opt for a sailing course that includes island-hopping around the Ionian Islands.

When to Travel: Late spring to early autumn for the best sailing weather.

How to Get There: Fly to Corfu International Airport or take a ferry from mainland Greece.

4. The Whitsundays, Australia

The Whitsundays, a collection of islands off Queensland’s coast, offer a tropical paradise for sailing novices. The Great Barrier Reef provides sheltered waters, ideal for learning. Sailing courses here often include snorkeling and exploration of the reef.

Insider’s Tip: Choose a sailing school that offers an introduction to sailing in the Great Barrier Reef for a unique experience.

When to Travel: May to September for cooler temperatures and optimal sailing conditions.

How to Get There: Fly to Hamilton Island and take a ferry or boat to your chosen island.

5. Cowes, Isle of Wight, UK

Cowes is a historic sailing town famous for the annual Cowes Week regatta. The Solent’s challenging waters provide an excellent training ground for beginners. Sailing schools in Cowes offer courses catering to all skill levels, set against British maritime heritage.

Insider’s Tip: Attend during Cowes Week for a thrilling introduction to the sailing community.

When to Travel: Summer for the best weather and to experience sailing events.

How to Get There: Take a ferry from Southampton or Portsmouth to the Isle of Wight.

6. Newport, Rhode Island, USA

Newport is a renowned sailing destination with a storied yachting history. Narragansett Bay’s varied conditions are perfect for beginners. Sailing schools in Newport, set in a picturesque New England town, offer a mix of practical training and theoretical knowledge.

Insider’s Tip: Participate in local regattas organized by sailing schools for hands-on experience.

When to Travel: Late spring to early fall for ideal sailing conditions.

How to Get There: Fly to T.F. Green Airport in Providence and drive to Newport.

7. San Diego, California, USA

San Diego’s consistent weather and diverse sailing areas make it an excellent place for beginners. San Diego Bay and the Pacific Ocean offer different sailing experiences. The city’s sailing schools provide a range of courses in these spectacular settings.

Insider’s Tip: Take advantage of San Diego’s ideal weather for year-round sailing activities.

When to Travel: Year-round, with the most stable conditions from spring to fall.

How to Get There: Fly directly into San Diego International Airport.

8. Split, Croatia

The historic city of Split on the Dalmatian coast offers idyllic conditions for learning to sail. The Adriatic Sea’s calm waters and the region’s many islands create a perfect sailing playground. Sailing schools in Split combine instruction with the exploration of Croatia’s stunning coastline.

Insider’s Tip: Include island visits to experience Croatia’s diverse maritime landscapes in your sailing course.

When to Travel: May to September for calm seas and pleasant weather.

How to Get There: Fly to Split Airport or travel by ferry from other parts of Croatia.

9. Tortola, British Virgin Islands

Tortola, part of the British Virgin Islands, is a Caribbean gem for beginner sailors. Its protected waters and steady trade winds offer ideal sailing conditions. Sailing schools on Tortola provide comprehensive beginner courses in this tropical paradise.

Insider’s Tip: Combine sailing lessons with snorkeling and beach visits for a complete Caribbean experience.

When to Travel: December to April for the best sailing weather.

How to Get There: Fly to Terrance B. Lettsome International Airport on Beef Island, which is connected to Tortola by a bridge.

10. The Florida Keys, USA

The Florida Keys offer a unique sailing experience with their shallow waters and coral reefs. The Keys’ relaxed atmosphere is perfect for beginners. Sailing schools here focus on practical skills in a laid-back environment.

Insider’s Tip: Extend your sailing trip to include a visit to Key West for its vibrant maritime culture.

When to Travel: November to May for the best weather and sailing conditions.

How to Get There: Fly to Miami International Airport and drive to the Keys or fly directly to Key West International Airport.

11. Antigua, Caribbean

Antigua is renowned for its 365 beaches and excellent sailing conditions. The island’s consistent winds and clear waters are ideal for beginners. Sailing schools in Antigua offer courses that let you explore the Caribbean Sea’s beauty.

Insider’s Tip: Time your visit to Antigua Sailing Week to witness world-class racing.

When to Travel: December to April for optimal sailing conditions.

How to Get There: Fly directly to V.C. Bird International Airport in Antigua.

12. Vancouver, Canada

Vancouver’s scenic coastline and diverse marine environments make it a fantastic location for learning to sail. The city’s sailing schools provide courses in the sheltered waters of English Bay and the Strait of Georgia.

Insider’s Tip: Take a sailing trip around the Gulf Islands for an unforgettable experience.

When to Travel: May to September is the most favorable weather.

How to Get There: Fly directly to Vancouver International Airport.

13. Saint Tropez, France

Saint Tropez, a glamorous destination on the French Riviera, offers a sophisticated setting for sailing beginners. The Mediterranean Sea’s mild conditions are perfect for learning. Sailing schools in Saint Tropez combine luxury with practical sailing instruction.

Insider’s Tip: Experience the glitz of Saint Tropez by visiting its famous beaches and restaurants.

When to Travel: Late spring to early autumn for ideal sailing weather.

How to Get There: Fly to Nice Côte d’Azur Airport and drive to Saint Tropez.

With its stunning barrier reef and numerous cayes, Belize is an extraordinary destination for beginner sailors. The Caribbean Sea’s warm waters and gentle winds create a relaxed environment for learning. Sailing schools in Belize often include reef exploration in their courses.

Insider’s Tip: Combine your sailing lessons with scuba diving or snorkeling to explore Belize’s rich marine life.

When to Travel: November to April for the best sailing and weather conditions.

How to Get There: Fly into Philip S. W. Goldson International Airport in Belize City.

15. Lake Garda, Italy

Lake Garda, Italy’s largest lake, offers a picturesque setting for learning to sail. Surrounded by mountains, the lake’s winds are predictable, making it an ideal place for beginners. Sailing schools around Lake Garda provide courses against stunning Italian scenery.

Insider’s Tip: Explore the charming towns around Lake Garda for a complete Italian experience.

When to Travel: April to October for the best wind conditions.

How to Get There: Fly to Verona Airport and drive to Lake Garda.

The Bottom Line

As you venture into the sailing realm, choosing where to begin this journey is crucial. Selecting a location and sailing school involves more than just finding picturesque waters; it’s about matching your learning ambitions with the right environment and expertise. Whether it’s the steady winds of the British Virgin Islands for a gentle start or the challenging conditions of the San Francisco Bay for a more rigorous approach, your decision should reflect your personal objectives and comfort level.

Consider practical aspects such as the climate, types of boats used for instruction, and the overall sailing culture of the area. Sailing is as much about understanding weather patterns and local maritime conditions as it is about handling the boat. It’s a skill that goes beyond the technicalities, encompassing a deep respect for the sea and its ever-changing nature.

Embark on this journey with a mindset geared towards learning and adapting. Sailing is a skill that offers a unique blend of adventure, tranquility, and a profound connection with nature. Each destination provides its own set of challenges and rewards, making your learning experience distinct. Your ideal starting point in sailing is out there, offering the thrill of navigating the waters and a pathway to new experiences and discoveries.

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The post 15 Best Sailing Destinations: A Guide To Sailing Schools for Beginners republished on Passing Thru with permission from The Green Voyage .

Featured Image Credit: Shutterstock / Ilija Ascic.

For transparency, this content was partly developed with AI assistance and carefully curated by an experienced editor to be informative and ensure accuracy.

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Sailing and boat tours in Greenport, Oyster Bay, Oakdale and Montauk

Passengers take in the views on the Waterfront Center’s oyster sloop Christeen sunset cruise in Oyster Bay. Credit: Marisol Diaz

On sailboat cruises from Oyster Bay to Montauk, you can relax on deck, cooled by sea spray and a glass of wine. Or you can get up off your cushion and join the hands on deck in Oakdale. 

Here's how to get a taste of cruising on Long Island's waters, whether destined for a swimming hole or merely a photo-worthy sunset.

Travel aboard the sailboat Layla, of Layla Sailing in Greenport. Credit: Randee Daddona

SAIL NEAR SHELTER ISLAND

ABOARD Layla, a 45-foot sailboat docked in Greenport

WHEN  May 27 to Sept. 2

INFO 631-319-0161, laylasailing.com

From the East End and NYC day trips to weekend road trips and beyond, get ideas on how to plan your travels.

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Capt. Liz Gillooly leads private sails from Greenport that explore the waters around Shelter Island. Options include shorter morning and sunset sails (from $750 for a private charter up to six passengers) and traditional half-day charters. Guests may bring their own snacks and drinks, catering options available.

The sloop Christeen is available for cruises at the Waterfront Center on West End Avenue in Oyster Bay. Credit: Jeff Bachner

SAIL WITH A SUNSET

ABOARD Christeen, a restored oyster sloop from The WaterFront Center in Oyster Bay

WHEN | WHERE  6 p.m. most days through Labor Day ($75 a person) from 1 West End Ave., Oyster Bay, reserve online. The center offers other sailing experiences, including a two-hour harbor tour ($55 a person), marine ecology cruises ($50 a person). Private charters available (starting at $1,275).

INFO 516-922-7245, sailchristeen.org

The view includes Gold Coast mansions lining tony Centre Island on cruises aboard the 40-foot sailboat. A U.S. Coast Guard-certified captain helms the ride through Oyster Bay Harbor and Cold Spring Harbor. You’ll learn about the history of Christeen, built in 1883 in Glenwood Landing and a National Historic Landmark since 1992.

Explore the seas of the East End on a sailing trip with Montauk's Catamaran Mon Tiki. Credit: Sailing MTK

SAIL WITH A SWIM

ABOARD  The Mon Tiki fleet of catamarans in Montauk 

INFO 631-668-2826, sailingmontauk.com  

The 65-foot Mon Tiki Largo, the 40-foot Mon Tiki and the 26-foot Mon Tiki Mini — all catamarans — are playfully named after explorer Thor Heyerdahl's Kon-Tiki. Amelia Ryan, who owns and operates the line with her husband, Capt. David Ryan, says the cruises explore a world beyond the chic resort community. “All of that falls away when you are out on the water with the sounds of the wind, the waves and the natural beauty,” which occasionally includes dolphin sightings, Ryan says. Passengers can bring their own lunch and beverages on a two- to three-hour private sail (starting $250) through early October, and there's plenty of time to take a plunge into the water from the vessel's swim ramp and paddleboards (life jackets provided).

The Priscilla oyster sloop, sailed by Capt. Robert Campbell in the Great South Bay. Credit: Debbie Egan-Chin

SAIL AND SIGHTSEE

ABOARD Priscilla, a restored 1888 oyster sloop from the Long Island Maritime Museum in West Sayville

WHEN | WHERE 4 p.m. Tuesdays-Thursdays, $45 ($20 kids) or dinner sail 4 p.m. Fridays, 1 and 4 p.m. Saturdays-Sundays ($75 includes $30 food voucher), reserve online. Arrive 30 minutes before sail time at the dock behind The Snapper Inn restaurant, 500 Shore Dr., Oakdale .

INFO 631-854-4974,  sailpriscilla.org

The Long Island Maritime Museum's historic oyster sloop Priscilla hosts two-hour cruises on the Great South Bay. Some sails have included options for lunch or dinner at The Snapper Inn restaurant in Oakdale. Sails include plenty of narration that covers the ship's history among a 500-boat fleet that plied the South Shore bays for oysters. The vessel was retired in the 1960s and restored in 2002. It became a National Historic Landmark in 2006.

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The complete sailing trip packing list- Here’s What to Pack

Clothing & personal sailing packing list items.

• Swimwear / swimsuits - you don't need one for every day, but they don't take up much space!
• Long-sleeved cover ups - there will be a point each day where it may be difficult to re-apply sunscreen. It's usually because you are wet - rain, sweat, dripping from a recent dip, etc. Having a couple of these sun shirts is a great idea to keep you protected from sunburn. For the guys, Florence Marine X - John John Florence's  brand - puts out a great SPF hooded shirt
• T-shirts/tank tops
• Sarongs for the ladies
• Dad hats for the guys

•   Lightweight rain coat or windbreaker - we usually encounter a squall or two and someone still has to drive the boat! These aren't bad either for a nighttime dinghy ride into the wind.
• Sweater - it can feel chilly at night at times
• Theme night - we usually pick one night to dress up and have some fun: Luau Night, Dinner with the Captain (think Master and Commander), etc.
• Polarized sunglasses - all the crew should bring polarized shares. They are helpful to read the water and see potential obstructions. My favorite brand recently is Electric - the Knoxville Sport model is a perfect everyday pair. Get them in Blue Polarized Pro for your boat trip.
• Snorkel & mask - I highly recommend bringing your own. Snorkeling gear is usually available from the charter company, but it gets a lot of use. The quality is not usually great either. Spend the money and invest in your own. I learned to scuba dive in 2008, and I am still using the same snorkel/mask. They will last you for years if taken care of. Another reason to bring your own is that, due to Covid, some charter companies are no longer providing masks (although you can still get fins from them).
• Fins - if you have them and have space, bring them. Otherwise, the fins from the charter company will usually be just fine.
• Walking/hiking shoes - these are usually the pair I wear on the airplane.
• Water shoes - optional, but they can be helpful. For example, jumping in the water to beach your dinghy. 
• Boat shoes - you definitely do not need these. I think most people that wear boat shoes have never been on a boat. I'm always barefoot when we are on the sailboat.
• Quick dry towels - most charter companies don't provide beach towels, so plan to bring your own. Since they might get multiple uses every day, we like quick dry options. This type of towel also won't take up as much space in your bag.
• Sunscreen lotion - if you can find it, bring a reef friendly option. Reef Safe Sunscreen is a bit more expensive, but it's worth it to help protect the reefs.
• Personal toiletries - toothbrush, toothpaste, lip balm, deodorant, shampoo/conditioner (the boat will not come stocked with this), etc.
• Electronic chargers

 Things to bring for the crew

• Fishing gear and tackle - check out our sailboat fishing guide for all the details.
• Group flag - such as our Yacht Warriors flag! I ordered a custom burgee from bestflag .

• Dramamine for seasickness, extra band aids, neosporin, aloe, etc.
• Cash - it's a great idea to have a couple hundred bucks for each person. You'll need it for purchases such as mooring ball fees, trash pickup fees, and some restaurants might be cash only.
• Extra zip lock bags of various sizes
• Board game, playing cards, or dominoes - whatever the crew likes if games are your thing
• Floats - if you can rent them, we'd recommend just going that route. You can pack your own, but they take up space and are likely going to be thrown out at the end of the trip. I've taken a MONSTER float on a couple trips, but it always becomes way more work than it's worth.
• Flashlight or headlamp - bring a headlamp if you have one, but if you need one, your smartphone flashlight will probably be fine for the boat. You might want a real flashlight if you plan to take the dinghy ashore for dinner and return after dark.
• Collapsible cooler - for those shore excursions or storing extra ice on the boat. For some destinations, you could also pack meat in dry ice to bring with you. I like the TOURIT coolers. It's soft, so it can be packed or used as a carry on. They are also much more affordable than higher end coolers like Yeti or RTIC.  
• Waterproof speaker - believe it or not, some sailboats don't have external speakers that you can hear well while underway. You'll want a waterproof, portable speaker so that you can also take your sailing tunes ashore .
• Reusable drink cups , such as Yetis (get them personalized for a great trip souvenir)
• Dry bag - you don't need anything big, just something to fit phones in for a dinghy trip ashore. I've had a Sea to Summit dry bag for years - a 4L version should be perfect.  
• Paracord (550 cord) - you will find some many uses for this: securing fishing poles, tying on flags, making croakies for your sunglasses. Lots of color options are available online.  
• Spices - we always bring a basic assortment, salt and pepper at a minimum
• Hot sauce - I always pack some of my favorite all around hot sauce - Marie Sharp's. In Texas, I can get it at the local supermarkets, but you can also pick it up online. 

• Charts and cruising guides
• Fishing licenses (check local regulations)
• Drone (optional) - you won't regret it. Check out our trips to the Exumas, Bahamas or British Virgin Islands for some examples. I also post these pictures on our instagram profile.  
• Chefs knife or knife sharpener (optional) - this might sound silly, but I usually pack a well-sharpened kitchen knife since we are usually checking luggage for our fishing gear. We do a lot of cooking and working with a dull knife is the worst (and also dangerous)!
• Projector (optional) - OK hear me out. Yes I know we are going on a boat trip to cut the cords and enjoy the islands. It is sooo much fun, however, to watch Master and Commander or another favorite sailing movie (Captain Ron perhaps?) on the boat. We don't do it every night, but once or twice is fun! We hang up a sheet with duck tape and connect the projector via bluetooth to the boat's sound system. Check out our projector setup on our  Exumas trip.

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We are a group of friends that offers in Catania sailing tours in Acitrezza and in Taormina. We also organize boat dinners and events for members of our organization.

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The warmth of the sun enhances the smell of the earth, which blends with the scent of the Mediterranean Sea brought by the breeze. 🥰 The flavors in this generous land are decisive and unique and stand in a delicious balance between land and sea. 🌊 So beautiful that you can not fall in love with it! 💖 Find out how on: 👉 https://siciliansail.com/ Il calore del sole esalta l’odore della terra, che si mischia al profumo del mar Mediterraneo portato dalla brezza. 🥰 I sapori in questa terra generosa sono decisi e unici e stanno in un delizioso equilibrio tra terra e mare. 🌊 Così bella che non puoi non innamorartene! 💖 Scopri come su: 👉 https://siciliansail.com/ . . . #siciliansail #siciliancoast #sailboats #sailinginstagram #boattime #wind #sailingworld #sailingadventure #vacation #nautical #sailinglifestyle #sails #mediterraneansea #sea #mediterranean #summer #catania #sicily #siciliansea ...

Dedicate 6 hours of pure relaxation, discovering the magic of this enchanting land! 🥰 Book now to reserve a seat for Catania Private Daily Sailing. Find out how on: 👉 siciliansail.com Dedicati 6 ore di puro relax, alla scoperta della magia sprigionata da questa terra incantevole! 🥰 Prenota subito per riservarti un posto per il Catania Private Daily Sailing. Scopri come su: 👉 siciliansail.com . . . #siciliansail #boat #catamaran #sailing #yachting #sailingworld #sailingstagram #sailingholidays #sailingboat #sailingship #travel #boatparty #catania #sea #sealovers #siciliantour #sicily #cataniaprivatesailysailing ...

To all the Mothers of the world today we dedicate a sea of happiness, a wave of serenity and a breath of joy! 💖 👉 siciliansail.com A tutte le Mamme del mondo oggi dedichiamo un mare di felicità, un'ondata di serenità e una ventata di allegria! 💖 👉 siciliansail.com . . . #siciliansail #siciliancoast #sicily #sailinginstagram #boattime #sun #summertime #sailingstagram #sicilia #sailingworld #mom #mothersday #mother #happymothersday #mamma #sailingadventure #instagood #vacation #style #fun #sunset ...

"Sicily is an unprecedented orgy of colors, scents, lights, a great pleasure." ✒️ Sigmund Freud Enjoy its wonders with our tours. 🥰 Find the one best suited to you on: 👉 siciliansail.com "La Sicilia è un’orgia inaudita di colori, di profumi, di luci, una grande goduria." ✒️ Sigmund Freud Godi delle sue meraviglie con i nostri tour. 🥰 Scopri quello più adatto a te su: 👉 siciliansail.com . . . #siciliansail #sailingstagram #sicily #sailingholidays #sailingboat #sailingship #yacht #travel #sailor #sailinglife #sailingtime #catania #sailingpassion #sailboat #relax #sicilytourism #boatparty #landscape ...

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Posh round-trip Vancouver-Hawaii cruise sailing for a steal

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Travellers looking to visit the Aloha state from Vancouver won't have to take a flight thanks to an affordable offer through Holland America Line (HAL). 

A couple of weeks in Hawaii including meals at upscale dining restaurants, five-star accommodation, entertainment, and flights from Vancouver International Airport (YVR) typically sets travellers back hundreds of dollars daily.

However, this fall cruise on HAL costs less per day including all of the above for just over $150 per day. 

Holland America is known for its mid-size vessels featuring a more traditional onboard experience. Fans of the cruise line typically enjoy sailing on ships they can become well acquainted with during the voyage and relish opportunities to speak with the captain and cruise director. 

The five-star Koningsdam departs Canada Place on Saturday, Oct. 5 at 3 p.m. and spends six days at sea before reaching Honolulu, Oahu. While this may seem like a long time to spend on the water, many travellers relish exploring the ship, trying out different restaurants, seeing impressive live entertainment, and relaxing on the high seas. 

The ship features two swimming pools, a live theatre, a tennis court, renowned spa treatments, movies under the stars, a basketball court, a video arcade, a casino, and much more. The "Pinnacle" class ship also allows guests to create a wine blend from a selection of single vineyard red wines.

The ship also includes a popular governing in Honolulu, meaning guests don't have to worry about rushing to the ship after a day in port. It also arrives early at 8 a.m. and doesn't depart until 11 p.m. the next day.

Guests are treated to a second overnight option in Nawiliwili, Kauai after they overnight in Oahu. 

Before heading back across the Pacific to Vancouver, the ship stops on the Big Island in Kona and Hilo. 

The cruise disembarks at Canada Place on Tuesday, Oct. 22.

What is included in the cost of the Vancouver-Hawaii cruise on Holland America Line?

Most cabin categories are still available for this sailing with Holland, including inside (interior), ocean view, verandah (balcony), Vista suite, and Neptune suite. Only the Signature Suite is sold out (see slide two).

An "inside" or interior stateroom for two people costs $5,366.64 or $2,683.32 per person. The per-diem, per-person amount is $157.84 for the 17-night sailing (see slide three). This is the lowest-priced option for two people. 

The cost of the cruise includes transportation on a beautiful five-star vessel, gourmet meals, entertainment, snacks, and lodging. The only thing it doesn’t factor in is alcohol, but purchasing a drink package can reduce the costs.

Hawaii offers a range of natural gems to explore on each island and numerous places to dine, shop, and catch live shows. From the Mauna Kea Summit to the massive, approachable populations of manta rays, the rich history of Lahaina to the stunning Waikiki Beach, the islands ooze tropical beauty.

• Related : Everything Vancouver travellers need to know to plan a trip to Hawaii

Have a look at my experience  sailing on this ship up the Pacific Coast in April 2022 .

Find more information about exciting destinations in B.C. and across the globe, as well as travel deals and tips, by signing up for  V.I.A.'s weekly travel newsletter The Wanderer . Since travel deals can sell out, find out the day they are posted by signing up for our  daily Travel Deals newsletter.

Want to learn more about a specific destination or have a travel concern or idea you would like V.I.A. to write about? Email us at  [email protected] . Send us stories about recent holidays that you've been on, or if you have any tips you think our readers should know about. 

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7 best cancun tours: chichen itza, snorkeling & more.

These excursions will show you what lies beyond the city's bright beaches.

The Best Cancun Tours

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Experience some of Cancun's history with a visit to Chichen Itza.

From Mayan ruins to the turquoise Caribbean Sea to abundant coral reefs, there is so much to see in and around Cancún . To make the most of your time on the Yucatán Peninsula, consider signing up for a guided tour. U.S. News selected the top Cancún tours by relying on expert opinion and traveler sentiment. Whether you pick an easygoing bus tour or a thrilling speedboat excursion, you're sure to have the adventure of a lifetime.

Amigo Tours – Chichen Itza VIP Tour

Price: From $52 Duration: 12 hours

To beat the crowds at the ancient Mayan site of Chichén Itzá , this excursion starts at 6 a.m. After picking you up at your hotel, a bilingual guide leads the full-day, 12-hour tour of the UNESCO World Heritage Site while giving a history of Mayan culture and the ruins. The tour also includes a buffet lunch, a tequila tasting, the opportunity to swim in a cenote (a natural well) and a visit to the city of Valladolid. Reviewers enjoy the swim and praise their guides, while others advise bringing bug spray and cash for additional fees, including the historic site's tax and a life vest rental at the cenote.

Tours, which are offered daily and include pickup at a location of your choosing, start at $52 for participants 3 and older; children younger than 3 can join for free. The company also offers tours of the site at sunrise, as well as tours of Tulum and Isla Mujeres , among others.

View & Book Tickets:  Option 1 | Option 2

Jungle Tour Adventure Cancún – Speedboat & Snorkeling Tour

Price: From $45 Duration: 2 hours

Travelers on this two-hour excursion will drive their own speedboat while exploring mangrove canals and the Punta Nizuc bay alongside a guide. Afterward, tourgoers will snorkel through the clear waters of the Punta Nizuc coral reef. Reviewers say the tour is super fun and appreciate the guides' attention to safety.

Tickets start at $45 per person for a shared boat. Solo travelers will pay about $80 for their own boat. Additional dock fees (about $20) are not included in the ticket price. Children must be at least 4 years old to participate and some health restrictions apply. Tours operate at 9 a.m., noon and 3 p.m. daily. No boating experience is required. The company also runs a mangrove tour using the speedboats.

View & Book Tickets: Viator | GetYourGuide

Contoy Adventures – Contoy Eco Adventure

Price: Adults from $110; kids from $85 Duration: 7.5 hours

Only 200 people per day are allowed to visit Isla Contoy , a protected natural reserve and bird sanctuary north of Cancún. Contoy Adventures takes you by boat to this preserved area, where you will have ample opportunities to swim and snorkel after you take a guided tour of the island. You'll also stop at Isla Mujeres on the way back to Cancún. Reviewers say they enjoy the excursion, but note that the stop at Isla Mujeres is short without much time to explore.

Tickets start at $110 per adult and $85 per child ages 5 to 11; kids 4 and younger cost $45. Breakfast, lunch and pickup from select hotels are all included in the ticket cost; however, a $20 fee that covers dock and national park fees must be paid in cash the day of your tour is not. The tour runs from about 9:30 a.m. to 5 p.m. on Monday through Saturday. Contoy Adventures also offers whale shark tours, among others.

Courtesy of EcoColors Tours

Though large, whale sharks are gentle and safe to swim with. Meet these creatures on a tour with EcoColors.

EcoColors Tours – Whale Sharks Cancun Tour

Price: Adults from $195; kids from $169 Duration 5 to 8 hours

This adventure gives travelers the opportunity to swim alongside magnificent whale sharks. Guides lead the small-group tours to the whale shark feeding ground, where travelers can snorkel alongside the gentle giants. After snorkeling, you'll stop on Isla Mujeres to relax. Tourgoers describe the excursion as an amazing experience and report seeing many whale sharks. Others advise taking motion sickness medicine before boarding the boat and wearing rash guards or bringing cover-ups for the trip, as you cannot wear sunscreen (even reef-safe sunscreen options) for environmental reasons.

Tours, which last approximately five to eight hours, are offered May to mid-September. Tickets start at $195 for participants 8 and older and $169 for children ages 5 to 7. Tickets include snacks and lunch, but not the dock and environmental taxes, which are $15 per person and must be paid in cash. Patrons must be at least 5 years old to participate. Tours pick up at hotels in Cancún around 7 a.m.; they also pick up from Playa del Carmen at 6 a.m. EcoColors Tours offers other nature tours, such as a sea turtle snorkeling tour.

Ocean Tours – Tulum Ruins, Cenotes and Snorkeling Tour

Price: Adults from $119; kids from $99 Duration: 10 hours

If you want to enjoy a day trip to Tulum, but don't want to deal with the logistics of planning your own transportation and activities, consider this popular tour. Tourgoers take a morning guided tour of the Tulum archaeological site , snorkel at Tulum's beach alongside colorful fish and stingrays, and swim in two cenotes. Reviewers praise their guides and recommend the tour, saying it is fun and worth the cost.

Tickets start at $119 for adults and $99 for children ages 4 to 11, and include lunch, snacks and refreshments, but do not include the $15 marine fee. Pickup from area accommodations begins at 6 a.m., and the tour concludes around 4 p.m. Ocean Tours also offers excursions to Coba , Isla Contoy and Isla Mujeres, among others.

KayTours Mexico – Puerto Morelos

Price: Adults from $195; kids from $180 Duration: 8 hours

This adventurous private tour includes snorkeling in the national marine park of Puerto Morelos followed by a visit to several cenotes for activities like rope swings and zip lines. Reviewers highly recommend the company and describe the tours as fun and amazing.

The full-day tour runs daily and you can select your own pickup time between 7:15 and 11 a.m., though the company recommends a pickup no later than 8 a.m. Tours include lunch and snacks, as well as round-trip transportation. Ticket prices vary depending on the number of people in your group; a couple can expect to pay about $195 per person; fees for children ages 4 to 17 start at $180. KayTours Mexico also offers excursions to Mayan ruins, Las Coloradas pink lake, whale shark tours and more.

Cancun Sailing – Plus Experience Tour to Isla Mujeres

Price: Adults from $89; kids from $59

Duration: 7 hours

Public ferries from Cancún to Isla Mujeres are readily available, but if you're looking for a tour option that allows for swimming and snorkeling, reviewers say this excursion from Cancun Sailing fits the bill. The seven-hour catamaran tour also includes transportation, a buffet lunch and an open bar. Plus, you'll have time to explore Isla Mujeres on your own. Reviewers describe the tour as fun but wish they had more time for snorkeling. They also note there are heavy crowds at the snorkeling stop.

Tickets start at $89 for adults and $59 for children ages 5 to 10. Children 5 and younger can join for free, though Cancun Sailing recommends alerting them if you're traveling with kids so they can place you on a more family-oriented tour. Cancun Sailing also offers a few premium experiences of this tour that can include snacks, a luxury boat and more free time.

View & Book Tickets: Option 1 | Option 2

You may also be interested in:

• The Best Things to Do in Cancun
• The Best Puerto Vallarta Tours
• The Best Mexico City Tours
• The Best All-Inclusive Resorts in Cancun
• The Best Cancun All-Inclusive Family Resorts
• The Best Adults-Only All-Inclusive Resorts in Mexico

Tags: Tours , Vacations , Travel , Mexico

World's Best Places To Visit

• # 1 South Island, New Zealand
• # 4 Bora Bora

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