sailing tours long island

The Ginny Marie Schooner

Traditional Sailing Tours out of Port Jefferson, NY

An Old World Sailing Experience.

Experience the beauty and elegance of a bygone era aboard the Ginny Marie, a stunning 50-foot William Atkin topsail schooner operated daily for pleasure cruises. Departing from Harborfront Park in Port Jefferson, NY, the Ginny Marie offers Long Islanders and tourists alike a vintage-style sailing experience like no other.

SAILING DAILY

Sailing daily sailing daily.

2 Hour Cruises Sailing Daily.

May 1st through August 14th: 10am, 1pm, 4pm, & 6:00pm sunset sail

August 15th through October 30th: 9:30am, 12:00pm, 2:30pm, & 5pm sunset sail

Maximum of 6 Guests per trip.

Gift Cards are available for purchase at the booking page!

Meet Captain Brian Murphy.

Captain Murphy is a true son of the sea, born and raised on Long Island, New York. Since he was a young boy, Brian has been drawn to the ocean - his happy place. He made a living as a clammer on the Long Island Sound for many years. Needing more security for his family, he turned in the clam rake for scrubs and became an ER Nurse at Stony Brook Hospital. After 15 years, he couldn't ignore the sea's call any longer. Thanks to the support of his wife, Ginny, and his two children, Lauren and Brian, he retired early and returned to the water to share his love of the sea with others. Today, he expertly captains the Ginny Marie, a stunning William Atkin topsail schooner, and provides passengers with an unforgettable sailing experience on the Long Island Sound.

The summer of 2024 is here!

Join us as we voyage through the beautiful bays of Long Island, New York. Our journey will include Baldwin Harbor, Mansion Harbor, Randall Bay, and Parsonage Cove: experience picturesque sunsets, gentle bay breezes, and calm, sheltered waters. Enjoy a Cash Bar, DJ, and dancing, making this a must-do activity for the summer.

Sunset Cruises

2-hour Cruise through Baldwin Harbor, Mansion Harbor, Randall Bay, and Parsonage Cove. Gentle bay breezes and calm sheltered waters along with a Cash Bar, DJ, and Dancing. Check out the calendar as our Sunset Cruises will be changing times with the season!

Learn More - Sunset Cruises

Specialty Cruises!

Hey there! Don't miss out on our special offer - come join us on a doggie cruise! Your furry friend rides for free with your ticket. 

Learn More - Specialty Cruises

Ask us about a Private Event!

Looking for the perfect boat to make your event unforgettable? Look no further! We have a wide range of boats available for all occasions, from birthday parties to school events. Get in touch with us today and let us show you what we can do to make your event a success!

Captain Lou VII

Atlantic Pearl

Starstream VIII

Nautical mile cruises is cruising around social media.

Keep up with all of our content and updates by following us on Instagram , Facebook , Twitter , and TikTok .

Get our latest content right in your inbox!

Join our mailing list to get information and updates on upcoming cruises.

By clicking Submit you consent to being placed on the Nautical Mile Cruises Mailing List

Take a quick look at our FAQ page for information regarding our cruises!

Sail the East End in comfort and style.

Welco me Ab oard!

Join us for a private charter or a public sail  aboard 

Schooner Bonnie Lyn n   or Classic Yacht  Surprise.

Sailing daily from Greenport or other North Fork & East End ports by request.

Our professional and friendly crew will ensure that your time on the water is fun, safe and memorable.

Bonnie Lynn

72-foot custom schooner

Private day & multi-day charters

Weekly public sails

Up to 32 guests

57-foot classic wooden ketch

Private day charters

Up to 6 guests

Sail With Us

Private Charters

The Perfect Venue

Day and sunset sails for groups of 1-32 guests.  Choose from Surprise  or  Bonnie Lynn  for an incredible day on the water.

Public Schooner Sails

Get on the Water

Open to the public! Join us for a casual sail on Bonnie Lynn  departing from Greenport every week.

Overnight Charters

The Best Way to Travel

All-inclusive, multi-day excursions aboard Bonnie Lynn . New England in the summer, Bahamas in the winter.

Testimonials

I can't think of a more peaceful, fun or civilized way to spend a day than sailing, and doing so with Hannah and Eric of East End Charters is the best way to do this on the North Fork

Five star experience and I would recommend it to all that seek a relaxing morning, afternoon or evening on the water on a beautiful sailboat, with a gracious crew allowing for good times on the sea!

The Rios Family

Beautiful boat. Impeccable, friendly service, in an easy, companionable manner... It felt luxurious, and it was.

 Would highly recommended East End Charters to any family looking for a relaxing and fun filled afternoon on the water.

Read more on                       TripAdvisor     Yelp     Google     Facebook

Follow us on

631-268-6528

[email protected]

1100 Manhasset Ave.

Greenport, NY 11944

Gift cards available

© 2024 by East End Charters, LLC

Privacy Policy

Your browser is not supported for this experience. We recommend using Chrome, Firefox, Edge, or Safari.

Get Inspired

Get the travel guide, become an insider, 12 cruises, boat rentals, tours & more for experiencing long island boating.

With hundreds of miles of captivating coastline, it goes without saying that boating on Long Island is a huge commodity. Whether you’re a boat owner or not, there are endless opportunities to set sail or tie up and enjoy this favorite Long Island pastime.

Set sail from Bay Shore Marina on relaxed sunset dinner cruises, or cruise around our famed lighthouses aboard a turn-of-the-century style riverboat. Sail into the sunset in Gold Coast style aboard a yacht charter.

Try the Moon Chaser Cruise that launches from Captree State Park, or a day at anchor with Over The Top Water Sports in quaint Northport Harbor. If you’re in the mood for an adventure, book a spot on a whale or seal watching cruise or a wetland exploration outing. Long Island is a boater’s paradise.

Long Island Boat Rentals (Port Washington, NY)

A fantastic way to experience the water with sweeping views of Long Island’s rocky Gold Coast is with Long Island Boat Rentals in Port Washington. Experience luxury when you charter a yacht and explore the North Shore with views of the Statue of Liberty or host your own “flarty” party (float party) for a celebration your guests will rave about for years to come. Long Island Boat Rentals also offers private training classes and adventure tours complete with wakeboards and other water-sporting accessories. It’s your one-stop-shop for nonstop fun on the water!

Insider’s tip: Visitors who purchase a 5-pack rental package will also receive 15% off on all rentals.

Viking Fleet (Montauk, NY)

Located in Montauk Harbor, Viking Fleet is your destination for year-round fishing trips, seasonal fast ferry service, excursions, and private charters. With a variety of trips to choose from, you can set sail on a Whale Watching Tour where you’ll cruise by the Montauk Lighthouse and see majestic marine wildlife or hop on a Sunset Cruise which takes you through the scenic waters of the East End and offers a selection of alcoholic beverages at the bar. Book a trip today for the upcoming summer season!

Never Ends Charters + Montauk Distilling Company (Montauk, NY)

Sponsored by Montauk Distilling Co., Never Ends Charters offers private boat cruises in Montauk for your next on-the-water outing. Choose from packages that include delicious picnics, stops at restaurants like Duryea’s, Navy Beach, Inlet Seafoods, and Montauk Yacht Club, guided meditations with a relaxing sound bath, and so much more. Cruise in luxury as you explore Lake Montauk, Fort Pond Bay, and Block Island exclusively with Never Ends Charters.

Peconic Star Fishing (Greenport, NY)

Come set sail on a local fishing adventure with Peconic Star Fishing . On Peconic Star III, you can sail all day long fishing for porgies on the tip of Long Island’s North Fork or reserve the Peconic Star IV which offers weekend half-day options and weekday charters where you can reel in porgies, sea bass, weakfish, fluke, stripers, and more! All open boats feature heated cabins with dinettes and huge upper-level sundecks so the whole family can sail in comfort, as well as providing rods, bait, and tackle for the optimal fishing experience.

East End Charters (Greenport, NY)

On the other end of Long Island, sail in style and comfort on the beautiful waters of Greenport Harbor when you book with East End Charters . Board the Surprise , a private six-guest custom-built wooden ketch with stable, easy motion and elegant form. Surprise 's bright and spacious interior, large cockpit, and copious deck space offer plenty of room to relax, socialize, and enjoy the peacefulness of being on the water. With options from relaxing morning sails to luxurious overnight stays, East End Charters is the premier destination for luxury sailing.

Over The Top Charters (Northport, NY)

Credit: Kevin Cryer-Hassett

Whether your vibe is ripping through some waves, a day at anchor, or capturing photos of sprawling hillside Victorian estates, you’ll have a blast while experiencing terrific views of Northport Harbor. In addition to offering water sports such as wakeboarding, wakesurfing and waterskiing, Over The Top Watersports also offers sunrise, sunset, and dinner cruises! Visit them now for an over-the-top experience you won’t forget.

The Moon Chaser Cruises (Babylon, NY)

Departing from Captree State Park on Long Island’s South Shore and adjacent to Robert Moses State Park, board this impressive 200-passenger charter for an unforgettable night of great music and delicious food at an iconic waterfront eatery. On the Moon Chaser , you can soak up the sea air, sway to the music, and enjoy the party atmosphere as you dance to a cover band on the Bay Jam Cruise . Alternatively, board the Fire Island route on Flynn’s Dinner Cruise and observe fantastic views of the iconic Fire Island Lighthouse on your way to dinner at Flynn’s , Fire Island’s most famous restaurant! The Moon Chaser also offers four-hour packages for private parties, perfect for your next on-the-water celebration.

Cross Sound Cruises (Orient Point, NY)

Cruise in style when you go sightseeing with Cross Sound Cruises . Departing from the Orient Point dock, the two-hour Long Island Lights Cruise shows you breathtaking sights on the coastal tip of Long Island’s North Fork wine region and takes you directly to the local lights of stunning landmarks, including Gardiners Point Island and the Orient Point Lighthouse, and also boasts views of nearby New London, CT. For only $33 per adult passenger on the Long Island Lights Cruise, Cross Island Cruise’s comfortable, climate-controlled high-speed vessels will make your summer bucket list a reality.

Captree Fleet at Captree State Park (Babylon, NY)

Located on the easternmost tip of Jones Beach Island, Captree Fleet offers plenty of opportunities for your ideal maritime adventure. Whether you seek to host the party of a lifetime with one of their private charters or are looking for an open boat to fish for the day, Captree has it all. There are also charter rentals available to rent for your next corporate party, field trip, or family celebration. Choose from a variety of boats and Captree will accommodate your party size and/or fishing needs – all at a great price!

Long Island Aquarium’s Atlantis Explorer Tour Boat

Get ready for an interactive and educational 2-hour adventure aboard the Atlantis Explorer Tour Boat . The Atlantis Explorer takes you down the Peconic River and into Flanders Bay and offers plenty of opportunity for hands-on exploration with local wildlife. Group tours are available daily, and no aquarium admission is required to ride the tour boat. Check out their website for more details on this exciting excursion.

Discovery Wetlands Cruise (Stony Brook, NY)

This summer, let the Discovery take you through the historic hamlet of Stony Brook. This 27-passenger vessel cruises through the Ward Melville Heritage Organization’s 88-acre preserve for a tour through the wetlands. While on board, an expert narrates the wildlife that passengers observe and the natural history of the area, all in a one-and-a-half-hour trip. Experience Stony Brook Harbor like never before with the Discovery Wetlands Cruise !

Freeport Water Taxi and Tours (Freeport, NY)

Experience the South Shore like never before with Freeport Water Taxi and Tours . Book a classic one-hour Long Island cruise where you’ll voyage through the Woodcleft Canal and explore the wonderful inlets and bays of Long Island’s South Shore on this fun and relaxing boating experience. Other popular cruises include their Happy Hour Cruise, Sunset Cruise, and Seal Watching Cruise. Come explore the waters of Long Island on a boat tour today!

Download a copy of the Inspiration Guide for inspiration and more information to plan your perfect getaway.

Get the inspiration guide

Become an Insider

With the Long Island e-newsletter delivered two Fridays a month for information on signature events, special offers and regional inspiration.

Harbor Sailing Charters, Inc.

P.O. Box 301, Port Jefferson, NY 11777     631.473.4500                                   www.harborsailingcharters.com [email protected]

Harbor Sailing Charters  Port Jefferson

Sailing Cruises in Port Jefferson Harbor and Long Island Sound

At the Village Dock, Harborfront Park, Port Jeff

Our passion is bringing traditional schooner sailing back to Long Island!  Port Jefferson built over 500 traditional sailing schooners in its boat-building heyday, and we are dedicated to honoring our rich maritime tradition by taking you out to enjoy a cruise in the harbor or sound!  Come sail with us!

Daily Afternoon and Sunset Cruises

Harbor Sailing offers three cruises per day aboard the storied traditional

gaff-rigged Schooner Elizabeth leaving from the Village Dock at Port Jeff!

Early Afternoon Cruise

1:00 - 2:45pm

Late Afternoon Cruise

3:00 - 4:45pm

Sunset Cruises

5:30 - 7:15pm

Private Charters

Exceeding Expectations

Sailing Lessons

Personalized Approach

Special Events and Overnight Trips

Everything You Need

Upcoming Events

P.O. Box 301

Village Dock, Harborfront Park Port Jefferson, NY 11777

[email protected]

631.473.4500

Thanks for submitting!

Captain Steve's Sailing Charter

Captain Steve offers private sailing charters aboard Sales Call,  a 34 Foot Beneteau Oceanis for up to 6 guests. Customizable to whatever type of sailing adventure you are interested in, we are here to help. Sit back, relax and soak up the sun, we got you covered! Take the helm, unfurl the sails, the boat is yours to command. Drop the anchor, go for a swim, uncork the wine, no problem. Whatever the request, just ask!

Available for Any Special Event

Romantic Getaway

Watch the Sunset

Family Time

Proposals, Engagements and Weddings

Private and Group Sailing Lessons

See Historic Lighthouses

Perfect location for Social Media & Photo Shoots

Dock and Dine

Anchor, Swim and Chill

Why Choose Us

Highly experienced and U.S. Coast Guard Certified 

Top notch vessel and equipment

"Beyond the ordinary" customer service

Location, Location, Location

Create memorable experiences

Our Gallery

What to Expect on Board

Captain Steve sails out of Manhasset Bay in Port Washington. Come see the mansions of the Gold Coast of Long Island, sail under the Whitestone and Throgs Neck Bridges. Cruise to City Island for a Dock N Dine experience like no other. Drop the anchor by Half Moon Beach in Sands Point, go for a swim, chill, watch the sunset.

Do you have any questions?

Our most popular excursions.

Sailing Lessons

             Private Sailing Lesson

If you want to learn how to sail or brush up on your skills. I offer hands on sailing instruction and practice for beginners and experienced sailors.

$150 per hour Monday - Friday

2 hour minimum per session  

Limited to 3 participants per session

Sunset Sail

3 hour private charter weedays

Set sail on the coast of the Long Island Sound to see the magnificent sunset over the NYC skyline. Perfect for families, proposals, anniversaries, birthdays and celebrations!

Sunset Sail. 6 Guests Maximum

3 hrs for $650  Weekdays

1/2 Day Sail

              4 Hour private charter 

Enough time to sail under the Throgs Neck and Whitestone Bridges or head East to the Execution Rocks Lighthouse, see the Mansions of the Gold Coast, drop the anchor. 6 Guests Maximum

4 hrs for $775  Weekdays

Our Reviews

My family and I had a great day on the water with Captain Steve, who made the experience fun, as we cruised the Long Island sound, with a solid 10-15 knots worth of wind. The highlight was when my daughter took the 'wheel' and steered the boat, and felt the wind in the sails...she's hooked.

• What are your rates? All Charters are customizable to suit your needs. Tell Captain Steve exactly what you are interested in and he will curate a charter to meet your needs and exceed your expectations. Rates - 2 hour minimum, includes up to 6 passengers and USCG certified Captain $200 per hour Weekdays $250 per hour Weekends $300 per hour Holidays Sailing Lessons Monday - Friday 8 am- 4 PM only - 3 participants maximum - $150 per hour - 3 hour minimum
• What to expect onboard? Please arrive 15 minutes prior to your scheduled start time. Please also allow time to park, as there is no parking for Marina guest on the Hotel property. Once aboard, you will be briefed on safety procedures and discuss our sail plan. Sailing is an active sport, winds and sea state can change at anytime. A sailboat when under sail will heel (tipping to one side or the other caused by the force of the wind on the sails) That being said, it's nothing to worry about, the heeling effect can be controlled by the Captain and this sailboat will not tip over. You will also have the option to motor around (without unfurling the sails) or drop anchor for a more stable experience, giving you the opportunity to swim, dine, sun and chill on deck. The 2007, 34 foot Beneteau Oceanis 343 Sailing Yacht is equipped with a roller furling main and head sail for quick and easy departure and return. A large cockpit area that will comfortably seat 6 passengers. If interested, you will have the opportunity to take the helm, trim the sail and pilot the boat. There is a Bluetooth Stereo, TV, Head (bathroom), full kitchen ( refrigerator, microwave, stove and oven). There is swim ladder and platform with outdoor shower. There is also a collapsible Bimini top for shade. Please bring food, beverages, sun screen, hats, towels, sun glasses. Life jackets for children under 13. I have several available, if needed. Sorry, no Extra-Large hard sided coolers are allowed on board. All personal items must be secured for sailing in windy conditions. Barefoot on the boat is preferred, if not, please wear soft soled shoes. No shoes with heels are permitted on board. If winds are forecast to exceed 20 knots or thunderstorms are in the area, the Captain reserves the right to delay or postpone the sail for another date. Safety is top priority!
• What are the features of your boat? Bluetooth Stereo Bimini top for shade - collapsible for full sun Full Kitchen - microwave, oven, stove, refrigerator Head (Bathroom) with Shower Transom (back of boat) Swim platform with Shower Interior cabin with table Television Swim noodles Life jackets are available for everyone on board. You are welcome to bring food and beverages, including alcohol. Just a quick reminder to drink responsibly, the Captain has the right to terminate a charter due to intoxication. Note it is cooler out on the water, so bring extra clothes, especially for an evening cruise. Bathing suit and towel if you plan to swim. **Please note, no large hard sided coolers with wheels are allowed on the boat. You are welcome to bring to to them to the dock and items will be transferred to the refrigerator and smaller cooler on board.
• Whats your cancellation policy? We offer a full refund up to 7 days prior. 50% refund up to 3 days prior. Reschedule due to bad weather, it's the Captains Call. Saftey is our #1 priority!
• How many guests can I bring? U.S. Coast Guard requlations require that the # of guests be limited to 6 people regardless of age. Sorry no dogs or pets are allowed on board.
• Are Children allowed? Yes, but note this is not recommended for children under the age of 3. All children under 13 are required to wear a life jacket at all times when on deck. I have a several life jackets available, but for best fit, bring your own if available.
• Do you offer gift certificates? Yes, you can buy a Gift Card for any amount and apply it towards any sailing experience. Please find the link to Gift Cards below and in the main menu. https://www.captainstevesailing.com/gift-card
• Where do I get on board? Call or text Captain Steve for detailed directions 516-902-9099
• Where can I park my car? Please note that there is no parking available on the Hotel property for Marina guests. Metered parking is available on Main Street & the 'Passport Parking' app can be used to refill your meter remotely. Parking is also available across the street from the Hotel in the residential neighborhood or at the Port Washington Town Dock parking lot at 347 Main Street in Port Washington.
• What is the deal with inclement weather? We reschedule due to inclement weather. If the winds and seas are too rough for sailing we reschedule. If it's raining or lightning storms are tracking toward our area we reschedule. Sustained winds over 20 knots will warrant rescheduling. Note, many weather forecasts are for the Tri-State area, we generally sail within a 10 mile radius, and keep a close eye on the local weather.
• Is there a bathroom on board? Yes, there is a fully functioning bathroom on board. Toilet paper is located in the cabinet under the sink. To flush the toilet, you can move the lever to the left ( wet side) this will allow water to enter the toilet bowl when pumping up and down. To empty the toilet bowl, move the lever to the right and pump up and down until rempty. Please do not put anything inside the bowl aside from human waste or toilet paper. Paper towels of any kind will clog the plumbing system. There is a waste water holding tank that holds the waste and is pumped out once each week. There is no access to a public bathroom at the Fathoms Hotel for marina guests.
• What is a Community Sail? A Community Sail is a semi private sail where each seat is sold individually. There is a maximum of 6 guests. You can purchase 1-6 seats for a Community Sail based on availability for that date.
• Do you offer sailing lessons? Yes, I offer hands on sailing lessons. Monday to Friday only 8 am - 4 PM Private lessons only, limited to 3 participants per session. $150 per hour, 2 hour minimum per session

Get in Touch

Thanks for submitting!

[email protected]

516.628.7156

PRIVATE SAILING CHARTERS, SUNSET CRUISES & SAILING LESSONS IN OYSTER BAY, NY

Experience the beauty of long island's historic gold coast.

 Situated in the heart of Long Island's Gold Coast, just 30 miles from Manhattan, Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and the impressive estates that line the bay. 

In 2024, Oyster Bay Harbor was designated as ‘Best Harbor’ winner for the Mid-Atlantic region by the US Harbors organization! 

Home to former U.S. President Teddy Roosevelt, Oyster Bay is the only source of traditionally farmed oysters from Long Island providing up to 90% of all the oysters harvested in New York State!

SAIL IN COMFORT

You'll sail aboard  WINDSWEPT , a meticulously kept Jeanneau Sun Odyssey 36i featuring a spacious shaded cockpit and a secured deck. WINDSWEPT is professionally maintained and equipped with modern electronics and USCG approved safety gear. Whether you are celebrating a special occasion , interested in learning to sail, or planning a client outing, your time aboard WINDSWEPT will be both memorable and enjoyable!

S/V  W I N D S W E P T

2012 Jeanneau 36i

2-Hour Sailing Charter

Private sailing charter for up to 6 guests

3-Hour Sailing Charter

Half Day Sailing Charter

Full Day Sailing Charter

Popular charter experiences.

SUNSET CHARTERS

Sail into the sunset and enjoy one of the best shows on earth! View our photo gallery for some of our favorite Oyster Bay sunset photos!

SIGHTSEEING HARBOR TOURS

Learn about historic Oyster Bay Harbor while taking in the diverse wildlife and spectacular views of the sandy bluffs and mansions that line the bay!

SAIL & SWIM CHARTERS

Cool off and go for a refreshing swim before or after your sail! Water temperatures in Oyster Bay Harbor can reach nearly 80 degrees in August! WINDSWEPT is equipped with floats for everyone to enjoy!

SAILING LESSONS

Learn the basics of sailing a modern monohull. Private lessons cover everything from sail handling techniques, to sailing terminology, and the various points of sail!

PHOTOSHOOTS

Have professional photos taken with Oyster Bay and WINDSWEPT as your backdrop! Book time an hour before sunset for the best natural lighting!

TEAM BUILDING EXERCISES

Teamwork and effective communication are required to sail a boat well! Develop new skills while working together! Contact us to discuss your objectives and we'll create a great experience for your team! 

CLIENT OUTINGS

Take your client relationships to the next level with a memorable sailing experience aboard WINDSWEPT! Weekday sunset cruises are ideal for entertaining clients!

DOCK & DINE CHARTERS

Book a full day charter and sail to a nearby harbor! Head into town to try a new restaurant, indulge in a cocktail or check out an antique store! Finish the day with a relaxing sail back to Oyster Bay Harbor. 

GETTING TO THE BOAT

WINDSWEPT is moored in Oyster Bay Harbor, on the North Shore of Long Island. Upon booking, directions to the boat will provided in your confirmation e-mail. For those traveling from New York City, the marina is steps away from the Oyster Bay LIRR station or a 20-minute Uber ride from the Hicksville LIRR station. 

Oyster Bay has quite a few local attractions , restaurants, and bars that  you may want to consider before or after your charter, many of which are in walking distance of the marina! 

CAPTAIN JONATHAN

Owner/operator, uscg licensed oupv captain.

Jonathan is a lifelong sailor and U.S. Coast Guard licensed charter boat captain with decades of cruising, offshore and racing experience.  A Long Island native, Jonathan was taught to sail at an early age by his parents, who were avid sailors. Growing up, his summers were spent on the water sailing harbor to harbor on Long Island Sound.

FREQUENTLY ASKED QUESTIONS

What is the maximum number of people allowed per charter.

Your party can include up to 6 guests. Children are included in this limit, which is set by the U.S. Coast Guard for this type of charter and strictly enforced.

WHAT SHOULD WE BRING ON THE BOAT?

Your charter includes bottled water and a variety of soft drinks. You are welcome to bring your own food and beverages, including alcohol. We also encourage you to bring sunscreen. Shoes with non-marking soles are permitted (no shoes are preferred). Pack a bathing suit and towel if you'd like to go for a swim!

CAN WE CUSTOMIZE OUR EXPERIENCE?

Absolutely - in fact we would encourage you to! Call us to discuss the experience you envision and we will do our absolute best to accommodate! 

WHAT ARE THE SAILING CREDENTIALS OF YOUR CAPTAINS?

All of our Captains are licensed by the U.S. Coast Guard to operate sailing vessels up to 100 gross tons and have years of sailing experience.

I TEND TO GET SEASICK - SHOULD I BE WORRIED?

Oyster Bay is protected and typically very calm, even on windy days! That said, seasickness medication is carried onboard and can be taken proactively if you are concerned about getting seasick.

WHAT HAPPENS IF THERE IS BAD WEATHER?

Summer weather on Long Island can be uncooperative at times. While we cannot guarantee perfect weather for every charter, you are able to reschedule your charter at no cost if the forecast is calling for >40% of rain during the hours of your charter, heavy winds or lightning. In the event that we cannot find a date that works for your group, we will gladly issue a full refund.

WHAT IS YOUR CANCELLATION POLICY?

You may cancel or reschedule your charter at no cost up to 10 days prior to the scheduled date. If you cancel within 10 days and are unable to reschedule, you will receive a full refund minus your initial deposit.

CAN WE BRING A COOLER?

Absolutely, as long as it is a soft cooler!  Hard coolers can damage the deck when they are moved. WINDSWEPT is equipped with a YETI soft cooler that you are welcome to use. The boat also has onboard  refrigeration.

TESTIMONIALS

“Me and my husband booked a 3-hour sunset charter and were blown away by the natural beauty of Oyster Bay Harbor. Captain Jonathan was attentive and welcoming and the boat was beautiful! This experience was the highlight of our vacation and we would not hesitate to book again! 

- G. Moreira

Thanks for your inquiry! We will respond shortly!

2024 SAILING SEASON & HOURS

All hours subject to weather, april 27th - may 31st monday - friday: 5:30 pm -  9 pm saturday - sunday: 9 am - 9 pm june - august  monday - friday: 5:30 pm - 12 am  saturday - sunday: 9 am - 12 am september tuesday - friday: 5:30 pm - 10 pm saturday - sunday: 9 am - 10 pm october tuesday - friday: 5:30 pm - 10 pm  saturday - sunday: 9 am - 8 pm.

Looking Forward to Opening in May! Book Your Charter Now!

Freeport Water Taxi & Tours

Cruises & tours in freeport, ny, we are now open to 2024 season.  now taking bookings for 2024. sailing 7 days a week for both public and private tours & cruises, experience the south shore like never before, freeport water taxi & tours is truly happy to announce our re-opening on june 19.

We will be sailing on Thursdays, Fridays, Saturdays and Sundays only. The schedule will be as follows:

• Chevron down THURSDAY

6:00pm – HAPPY HOUR CRUISE

7:30pm – THEMED SUNSET CRUISE

• Chevron down FRIDAY
• 6:00pm – HAPPY HOUR CRUISE 7:30pm – SUNSET CRUISE (times vary depending on the Sunset – Check your reservation for exact times)
• Chevron down SATURDAY
• 12 Noon – ONE HOUR BAY NARRATED BAY TOUR 1:30pm – ONE HOUR BAY NARRATED BAY TOUR 3:00pm – ONE HOUR BAY NARRATED BAY TOUR 5:00pm – HAPPY HOUR CRUISE W/ LIVE MUSIC 6:00pm – HAPPY HOUR CRUISE W/ LIVE MUSIC 7:30pm – SUNSET CRUISE W/ LIVE MUSIC (times vary depending on the Sunset – Check your reservation for exact times)
• Chevron down SUNDAY
• 12 Noon – ONE HOUR BAY NARRATED BAY TOUR ***$5 Mimosas*** 1:30pm – ONE HOUR BAY NARRATED BAY TOUR ***$5 Mimosas*** 3:00pm – ONE HOUR BAY NARRATED BAY TOUR ***$5 Mimosas*** 5:00pm – HAPPY HOUR CRUISE W/ LIVE MUSIC 6:00pm – HAPPY HOUR CRUISE W/ LIVE MUSIC 7:30pm – SUNSET CRUISE W/ LIVE MUSIC (times vary depending on the Sunset – Check your reservation for exact times)
• Most Popular

One-Hour Long Island Cruise

Discover the wonderful bays of Long Island’s South Shores with this fun and relaxing one-hour cruise!

• Hour Glass 1 hour
• Users All ages
• Info Cruise

About Freeport Water Taxi & Tours

We are a cruise company that offers a wide range of boat tours and cruises on the South Shore of Long Island, NY. Some of our most popular Freeport Cruises include Sunset Cruises, Happy Hour Cruises, Daytime Bay Cruises, Seal Watching and Long Island Eco-Tours, Freeport party boats, boat rides around Long Island and much more! We also offer a shuttle service to and from Freeport & Point Lookout. Come explore the waters of Long Island on a boat tour today!

Cruise Through Our Five-Star TripAdvisor Reviews

Whether you live on Long Island or are from other parts of the world, you'll love this scenic boat tour. It's not only a great way to take in the natural beauty of the inlets and wetlands off of the South Shore, but it's also an opportunity to hear more about the water, the wildlife and the history of the area. Take your family or take a friend, you'll be sure to have fun.

I took my office on the Water Taxi for a sunset cruise with drinks. The skipper was terrific as was the entire crew. The office staff had the best time of their lives and the weather was perfect. I would highly recommend this to anyone looking for a respite from a busy day. Bring your office or your family or just go with a date. I could not say enough good things about our outing!!

We took an hour long sightseeing cruise. The journey took us along Woodcleft canal towards the inlets and bays south of Jones Beach. Although a lifetime resident of Long Island, I learned quite a few interesting things about the marshes and islets. The Captain and crew were friendly and accommodating throughout and we will definitely return!

This is a nice day just to relax and unwind .The crew was great. They were there to answer any questions. And truly enjoyed the jobs talking with everyone. They even took time out to take pictures with everyone. Definitely will be back again this summer.

We took the afternoon boat cruise and had a great time. The Captain and the co-captain were so welcoming and nice. They gave us information about the marine life in the area. I would highly recommend this boat trip. They gave us recommendations for restaurants in the area. We had a great lunch as well.

Excellent choice if you're looking for a relaxing evening with a love one or with the whole family. The boat ride was extremely enjoyable capturing the most amazing view of the sunset, listening to live music of the Caribbean gives you that wow factor of the whole experience.

went with a bunch of people for 80's & 90's music trivia. My group enjoyed answering the questions and laughing about our answers. The captain would point out various landmarks. I would recommend this company for any its events.

Experience breathtaking lighthouse tours

See history in a whole new light.

Cruise in comfort

Enjoy ice cold cocktails, delicious snacks, and other amazing amenities aboard our comfortable catamarans.

Our tours run for approximately 2 hours and are great for kids, friends, and family alike!

Each cruise is narrated by an experienced tour guide ready to regale you with tales of seafaring legends as well as the history of each notable sight and lighthouse.

Drift between sitting on sun soaked decks and our air-conditioned cabin and lounge.

Relax while soaking up panoramic views of the scenic shoreline.

Three exciting adventures,

…all at one affordable price..

Adults : $34 Children (aged 2-11): $17 Infants (under 2): Free

Classic Lighthouse Tour

Departing from New London , this tour passes by two Revolutionary-era forts before navigating towards Orient Point.

Those aboard our Classic Cruise pass the North Dumpling Light, Race Rock Light, Plum Island, and much more!

Skim our Classic Cruise guidebook.

Lights & Sights Cruise

After leaving New London , this tour heads east to Rhode Island and passes Latimer Reef Light, Simmons Castle, the Ocean House, Watch Hill Light — among others, on an adventure that merges maritime history with architectural gems.

Breeze our Lights & Sights guidebook.

Long Island Lights Tour

Departing idyllic Orient Point, guests will first happen upon Gardiners Point Lighthouse and The Ruins of Fort Tyler.

Heading north, this tour will pass the Little Gull, Race Rock, and Avery Point lighthouses before reaching New London Harbor and beyond.

Dip into our Long Island Lights guidebook.

More information

What to expect.

{*} Plan to arrive at least 30 minutes before your tour is scheduled to depart.

{*} Each cruise runs about 2 hours long so we recommend dressing comfortably, wearing sunscreen, and bringing whatever else you may need to fully soak in the sights.

{*} Once onboard, you’ll be able to breeze between our air-conditioned cabin and our sunny exterior decks.

{*} Get your camera ready for some stunning shots.

{*} Sit back, relax, and enjoy your cruise.

Departure Information

{*} Each lighthouse tour last approximately 2 hours.

{*} Reservations are strongly recommended.

{*} We’re always just a phone call away: (860) 444-4620

Click below to view our color-coded schedule. New London Schedule

Long Island Schedule

New London LIMITED parking is available at the New London terminal for $5 per calendar day. Other garage options exist nearby. read more Orient Point FREE parking is available on site at the Orient Point ferry terminal on a first-come, first-served basis read more

Lighthouse Preservation

Cross Sound Cruises is proud to support the efforts of the New London Maritime Society to save our local maritime heritage sites through education, advocacy and preservation.

Some of the lighthouses you will see on our cruises are owned and maintained by NLMS.

Please consider a donation to help support their efforts:

150 Bank Street

New London, CT 06320

National Lighthouse Day Promo

24% off all Lighthouse Cruises in August reserved before 8/10 using code NLD24 Details: Reservations required, and can be made on the website or through the call center. Reservations must be made between August 4th and August 10th 2024. Valid on all cruises departing OP and NL. Must be for cruises during the month of August 2024, not valid for cruises after August 31, 2024. Not valid on tickets already purchased and used. Cannot be combined with other discounts, including the group discount Can be used multiple times.

Part of the Cross Sound Ferry family

Our lighthouse cruises are brought to you by the same crew behind the iconic Cross Sound Ferry which has been in service since 1975.

Part of the Cross Sound Ferry Family

Prefer to book by phone? Drop us a line. (860) 444-4620

Swim along with us.

Find us on land. Cross Sound Ferry Services

2 Ferry Street, PO Box 33 New London, CT 06320

41270 Main Road Orient Point, NY 11957

Send us a message in a bottle. [email protected]

Terms and Conditions

• Sailing Charter Home
• Sailing Cruises
• Nautical Dreamer II
• Photo Gallery

Great South Bay Cruises

Explore the bay aboard Running Wild, our 52ft, 44 passenger luxury cruising yacht.

Private Cruises

For an unforgettable experience bring your friends and family aboard a Shoreline cruising yacht. Grab a drink and relax while we cruise through the calming Great South Bay off the coast of Long Island.

Daily Cruises

Come aboard the Running Wild and enjoy one of our daily cruises. Take a sightseeing cruise to explore the historical sights of the bay, or a sunset cruise to unwind. We have something for everyone. Trips depart from the Bay Shore Marina.

Special Events

Celebrate your special day out on the Great South Bay with Shoreline Trading Co. We can accommodate up to 44 guests to make your event a one-of-a-kind day to remember years to come.

Our flagship vessel is the 52 foot Running Wild. She is a beautiful single deck wooden yacht built from teak, mahogany, and pine. Running Wild can host up to 44 guests with a bar on board and hosts 360 degree views of the Great South Bay.

She gets her name from one of the infamous rumrunners found in the Great South Bay during the prohibition era.

Private Charter Cruises – Norwalk

Feed your soul on the open water.

SUNSET SAILS

Immerse yourself in the beauty of a spectacular sunset scene that will captivate your mind + body.

ALL-DAY SAILS

Check out charming inlets + discover coastline delights on this unforgettable all-day adventure.

• All Things To Do
• Amusement Parks
• Boating & Fishing
• Golf Courses
• Event Calendar
• Kids Entertainment
• Restaurants
• Summer Camps
• Vineyard Tours
• Calendar Of Events
• Places To Go
• Free Events
• This Weekend
• Next 7 Days
• Next 30 Days
• Add an Event
• Feature Your Event
• Business News
• Homes For Sale
• Homes By Town
• Search Properties
• Real Estate Services
• Long Island Realtors
• LongIsland.com's Fun Guides
• Discover Long Island's Travel Guide
• Port Washington Waterfront Guide
• LIRR Schedules
• Traffic Cameras
• Ferry Schedules
• Catering Halls
• Home Improvement
• Insurance Agents
• New Year's Eve Guide
• April Fun Guide
• Long Island Travel Guide (LICVB)
• Festivals & Fairs Guide
• Private Schools
• Things To Do
• Business Directory
• Bars & Clubs
• Car Dealers
• Wedding Services
• Feature Your Business
• Real Estate
• February Fun Guide

Long Island Cruises & Yacht Charters

• Cruises & Yacht Charters

Looking for a day of fun on the Long Island Sound? Cruise and charter services can take you all around the Island - literally! Whether you’re a party of five wanting to travel in style or a group of 30 trying to take in all the sights our home has to offer, there is a service to accommodate you. As long as you’re taking in the sights, you may as well savor the tastes as well; many cruise services will provide their own fishing poles and tackle to help you sample the local aquatic delicacies. Fish for fluke, flounder, striper, ... Read More Looking for a day of fun on the Long Island Sound? Cruise and charter services can take you all around the Island - literally! Whether you’re a party of five wanting to travel in style or a group of 30 trying to take in all the sights our home has to offer, there is a service to accommodate you. As long as you’re taking in the sights, you may as well savor the tastes as well; many cruise services will provide their own fishing poles and tackle to help you sample the local aquatic delicacies. Fish for fluke, flounder, striper, sea bass, porgies, blues and blackfish, and if you pick the right line you can let the crew worry about cleaning and filleting your party’s catch. When you’re ready to get your land legs back, some lines will take you to the beach where you can enjoy a quick swim or waterside barbecue. Show Less

Boating & Fishing

• Bait & Tackle
• Boat Builders
• Boat Cleaning & Detailing
• Boat Dealers - New & Used
• Boat Financing
• Boat Hauling & Transportation
• Boating Clubs
• Boating Gear
• Boating Magazines
• Boating Schools & Training
• Boat Insurance
• Boat Lettering & Graphics
• Boat Maintenance & Repairs
• Boat Rentals
• Boat Surveyors
• Boat Towing
• Boat Trailers
• Boat / Yacht Brokers
• Fishing Charters & Party Boats
• Jet Ski Rental
• Kayak & Canoe Rentals
• Marine Electronics & Equipment Dealers
• Other Boating Services
• Paddleboard Rentals
• Scuba Diving
• Seal Watching
• Shark Diving
• Water Sports
• Whale Watching

Featured Listing

American princess cruises, skyline cruises, tiki boat long island, captain gillen.

3500 Ocean Parkway in Babylon (631) 586-5511

Fun in the Sun Excursions

222 Old Neck Rd in Center Moriches, Long Island 631-807-1318

Long Island Private Yacht Charters

403 Main Street in Port Washington 516-761-0840

Want to be added to the Cruises & Yacht Charters Page? Call 631-406-4410 or Email Us for details!

Stories You Might Be Interested In

A.G. Schneiderman Announces Guilty Plea Of Fake Grant Writer Who Stole More Than $200,000 From Churches, Nonprofits, And Local Businesses

LongIsland.com's 2014 February Guide: Super Bowl Sunday, Valentine's Day & More!

Cruising Aboard a Fabulous Fishing Charter or Party Boat

Long Island's 2013 4th of July Guide: Fireworks, Festivities, Food & More!

Advertise With Us

Long Island's Premier Party Boat

Now taking reservations for 2024 season now taking reservations for 2024 season now taking reservations for 2024 season now taking reservations for 2024 season, it’s all about you, special occasion.

• Corporate Events
• Boys Night Out
• Family Reunions
• Micro Weddings
• Ladies Night
• Monday Night Football

Or… Just Because!

Choose Your Cruise

Celebrating or just seeking some fun? Our options cater to both small intimate groups of 2 and gatherings of up to 29. Whether you fancy an early start, a daytime voyage, a breathtaking sunset, or a moonlit escapade – it’s your day, your way!

Pick Your Day

Get ready to embark on an unforgettable adventure with your friends, family, and colleagues. No need to bring anything – we have it all. Eat, drink, & dance, or chill & enjoy the view. Take pictures, make memories, and relish in the adventure. When it’s time to wrap up, call your Uber.

Enjoy The Bar

Indulge in a diverse array of premium spirits, delightful wines, cold beer and impeccably crafted cocktails. Our talented bartenders will ensure you stay refreshed and well taken care of.

WANT FOOD TOO?

Save time and money by opting for our catering package. With a pre-arranged menu, you can avoid the hassle of last-minute decisions and enjoy cost savings compared to sourcing food individually.

Frequently asked questions

We are a “High End, Custom Built, Tiki Boat” specifically designed for: Private Parties, Corporate Events, & Public Charters.

• A Full Service Bar
• Large Dance Floor
• VIP Seating
• Big Screen TV
• Private Bathroom
• Lighting Systems
• Sound Systems
• Misters (for hot days)
• WIFI/ Bluetooth
• Panoramic Views

From a group of 2 (public charters) up to 30.

Catering & Open Bar options can be included

PUBLIC CRUISES

Like to mix & mingle, individual & small group tickets sold here., private parties, exclusively… for you & your crew, corporate events, a one of a kind long island team building experience, tiki boat long island, public cruise pricing.

Mon – Thur

Fri & Sun

TIKI BOAT LONG ISLAND private event boat pricing

*grand opening special*, monday - thursday, 90 minute tour, starting at $749, 3 hour premium tour (catering included), starting at $1899.

90 Minute Tour base prices cover up to 15 guests then $45 each extra guest. 3 Hour Premium Tour base prices cover up to 15 guests then $99 each extra guest.

This vessel can hold up to 30 guests.

Gratuity Is Not Included

Private Event Boat Pricing

Starting at $735.

Tour Start Times

Mon – Thu

90-Minute Tour base prices cover up to 15 guests then $45 each extra guest.

This vessel can hold up to 29 guests.

3 Hour Premium Tour base prices cover up to 15 guests then $89 each extra guest.

Catering Menu

Gift a tour.

Give the Gift of Tiki-Themed Fun!

the perfect gift

Season starts May 1st through October 31st

→Daily Public Cruises

→private parties, →corporate events.

Valid any date and any time during the season. You can even book the day of. How cool is that?!

About Tiki Boat Long Island

Tiki Boat Long Island is a tour operator based in, you guessed it, Long Island. Family-owned and operated, here at Tiki Boat Long Island we take pride in offering unique and unforgettable experiences to both the local community and visitors.

The family behind Tiki Boat Long Island also operates  Long Island Private Yacht Charters , a well-established business on Long Islands waterfront for over 6 years. In addition, they provide memorable experiences on the vessel Totally Outta Control, a luxury event yacht.

get in touch with us

Fill out our inquiry form to get more information on our team building activities in Long Island, and public or private cruises! Or, if you prefer to contact us directly, give us a call or send us an email, and we will get back to you shortly!

contact details

Phone: (631) 648-8055

Email: info@tikiboatli.com

Address: 445 Vanderbilt Blvd., Oakdale, N.Y. 11769

" * " indicates required fields

**We do not sell or provide your text message information to third parties.

* By submitting this webform, you consent to receiving periodic text messages from us. Message and data rates may apply. We assure you that your information will not be sold or provided to third parties. To opt out, reply ‘Stop.’ For assistance, reply ‘Help.’

SWITCH VESSEL

Long Island Boat Rentals

Located in Port Washington, Long Island offers Captained and Bareboat Rentals, Yacht Charters, Semi-Private Training Classes, Water Sports Adventures and On-the-Water Fun!

Are You Ready for an Adventure?

• Elixir Yacht Charters – luxury party yacht for up to 24 guests
• Memories on the Boat  – With Friends, Family, that Special Person, Coworkers and Clients!
• Water Sports – Tubing, Waterskiing, Wakeboarding and Swimming.
• Sunset Cruises – Romantic, Booze, Dock & Dine and Catered Cruises
• Sightseeing – Statue of Liberty, Manhattan, Gatsby Homes, Lighthouse, Historical and Local Destinations
• Fishing – For Fluke, Striped Bass, Bluefish, Blackfish and Porgies.
• Celebrate –   Birthdays, Reunions, Bachelor/Bachelorette and Engagements
• Captained Cruises
• Have a Flarty!
• Pick Your Adventure
• Rent a Boat
• Charter a Yacht
• Get Training

What’s Happening on the Water

Special events.

STAY TUNED FOR TICKED ELIXIR TRIPS IN JULY AND AUGUST 2023!

LIBR UPDATES

New carefree boat club location in huntington specials going on now for 2023, new yacht charters available see page for details, captain rentals & charters, captained rentals and elixir yacht charters are bookable online.

If your preferred date is unavailable, use the waitlist to secure your spot in line for Captained Rentals & Yacht Charters (6 passengers), and charter dates for “ ELIXIR ” our 24 guest luxury party yacht.  Select your vessel, date and check off “Captain Requested” to request captained services.

If you tried to book a bareboat rental that is currently booked, you can use the waitlist to be the first in line for a cancellation on your preferred date or boat.

Visit our info page for the waitlist and rate sheets.

Full Day Rentals Available – get the time in between half day rentals as a bonus and enjoy more time on the water!

Six (6) passenger maximum on all captained rentals, no exceptions.

Semi-Private Powerboat Training Classes offered Tuesday & Thursday mornings.

Purchase Gift Cards

liboatrentals Follow

Special Packages and Promotions

“ELIXIR” has launched! –  Our new custom designed party yacht for 24 guests

5-Pack – 15% off all your rentals if you rent 5 times. So easy, just pay as you go. Even without the 5-pack, on your 5th rental, we will give you the 15% discount. 

Military Discounts – 10% off for all active, retired, or reserve military veterans with a Valid Military ID.  $100 maximum per rental, not to be combined with other discounts/offers, may not be used to purchase gift cards or used on previous reservations.

First Responders 15% off – Monday-Thursday –  All active Police officers, Firefighters and EMTs receive 15% off our weekday rates on any of our boat rentals. Not to be combined with other offers or promotions.

Testimonials

This is my second great experience on a Long Island boat rental and it was wonderful. Gorgeous weather, courteous crew and lovely views. My husband and I can’t wait to come back again soon!

My brother-in-law was in town and we wanted to do something fun with him. He’d never been to LI, and we thought the best way to see it would be a cruise on the water. We rented a boat here after being referred by a friend, and we had a blast out there! It was just as exciting for us to get a different perspective on the island as it was for him. We don’t fish, but these boats would be perfect for that I imagine.

I reserved a 22.5 foot Scout online for 3 hours. We arrived and the boat was ready for us. Super clean and new motor looking. We were very happy with the young man who helped us and gave us guidelines of the waters there in Northport. Even though my husband is a seasoned boater. GPS system was perfect too. Very happy!

I have rented three times so far.  The boats are always in excellent condition, and the staff could not be more friendly or more helpful.  Get out on the water!

ADDITIONAL INFORMATION

• Frequently Asked Questions
• Boat Rental Wait List
• Renting vs. Buying
• Reasons to Get out on the Water
• Employment Opportunities
• Subscribe to Email

WE DELIVER!

Sound Sailing Center

Long island sound sailing school and membership club.

Long Island Sound

Adventure awaits.

Be sure to consult Eldridges for the tide charts when planning your trip. Never try to fight the tide near the race, unless you want to spend hours observing Plum Island. Also note that the current inside and outside of Long Sand Shoal can be moving in opposite directions, less than 2 miles apart!

Heading East

Moving to the east on the Long Island side is Port Jefferson (18nm away). As you enter the harbor, to the right is an unnamed bay which is highly popular with sailors.

My father called it Conscience Bay , and we probably anchored there 1,000 times (or so it seems) in my youth. Given the prevailing SW breezes, it’s usually a nice reach to and from Norwalk. Takes 3-4 hours in a 36 footer, 4-5 hours in an under 30 boat generally. You can also go into the town at the head of the harbor and pick up a mooring or dock. Danforth’s Restraint is popular. The sand pit, to your port as you pull in, has some shallow spots (I spent one afternoon on one after the boat swung around). The winds are shifty. Best left to the motorboats that crowd in, but it is fun for kids to climb and play on the cliff’s. Anchor just outside the sand pit.

After Port Jeff , the next harbor is Mattatuck (38 nm away), a narrow creek with only about 5 feet of water on low tide. There is a little room to anchor at the head of the harbor. Well protected, but nothing great.

The Connecticut side has many great harbors. From Norwalk, the first harbor is beautiful Southport (6nm away). No room to anchor, and only about 6′ in the outer channel at low tide. Call the yacht club for a mooring.

Next is Bridgeport (12 nm away). There is plenty of room behind the breakwater, and Pleasure Beach really is nice, but few boats stop here except for Tugs. I have spent a few nights in Bridgeport, and if nothing else, it sure is easy to enter in the dark due to all the lights. Bridgeport is getting better, with the baseball stadium and new marina planned, and it will become a better destination in time.

Black Rock , just to the east of Bridgeport Harbor, there are lots of little shops in Captain Cove Marina. Sort of a mini Mystic Seaport. Great yard, nice people. Stay away if the breeze does not have a westerly component, due to the treatment plant to the east.

After Bridgeport is Milford Harbor (no room to anchor, not too much to do), and little Charles Island (18 nm away), which you can anchor behind. Often crowded with day trippers, not many overnighters.

After the New Haven breakwater (not as good a stop as Bridgeport, but ok), comes my favorite spot on the Sound, the Thimble Islands (30 nm away). The Thimbles are huge hunks of Granite, and look like a chunk of Maine dropped in the Sound.

There is good holding ground in the mud between the islands. Stay away from the marked power cables. Enter in the daytime. There are numerous confusing buoys marking the many reefs. Once your in, it’s beautiful, if you like Maine. Unfortunately, the islands are all privately owned, so no exploring.

Adjacent to the Thimbles is Branford Harbor to the east, and Sachems Head to the West. Given the numerous reefs in the area, plot your courses carefully in advance, watch the depth like a hawk, and use lots of compass bearing to check your location. GPS is useless for threading around the reefs and islands. Sachems Head has a fine yacht club, but no space to anchor. There is plenty of space in the large harbor north of Sachems head, which is the place to go if the Thimbles are full up.

Past the Thimbles is Guilford , which is one of the prettiest town greens in Connecticut, a short 10 minute walk from the harbor. Unfortunately, the channel only carries about 4′ at low tide.

After Guilford, there is Westbrook and Duck Island Roads , which has a breakwater with 6-9 foot depths to anchor behind. Fairly exposed, lots of tide. I prefer to head up to Old Saybrook , and stay at the Dock N Dine (50nm from Norwalk).

Given the two lighthouses and prominent breakwater at the mouth of the Connecticut River, it’s an easy nighttime approach. If you grab dinner (or pull in between midnight and 11:00 in the morning), there is no charge to lie alongside the pier. Great spot to switch crews or pick someone up. Next door is a beautiful and very expensive resort marina, with a very good restaurant.

Five miles up the river is Essex , with a fine downtown and the great Griswold restraint. The Gris has one of the finest collection of ships prints in the country, worth more than the restraint. Stay at the Essex Island marina.

Four nm up is the beautiful fresh-water Hamburg’s Cove , and three more miles up is Gillette Castle. Another three miles and you’re at the Goodspeed Opera House, which is right on the river, with a pier. Probably can tie up, call ahead.

After the Connecticut River, the next great spot is Mystic , with the world renown Mystic Seaport. The bridge into Mystic only opens a few times a day, so get the opening times in advance.

It’s wonderful to stay one or two nights and be able to walk the grounds after everyone else has left. If you are a member, the dockage is a pretty good deal. You can also walk north to the Mystic Aquarium, or south to town, both of which are worthwhile.

There are also some Islands off Noank that you can anchor behind. After Mystic, Stonington and Fishers Island are a few miles away. Fishers Island offers beautiful estates, and not much else. I’ve anchored in both the west and east harbors in the J44, but neither are especially deep.

Stonington is also lovely, and Dodson’s boatyard is as nice as they come. Another great spot to do crew transfers. The downtown is beautiful, lots of antique houses and great dining establishments.

Through Plums Gut , Long Island begins to get interesting, with Shelter Island a wonderful spot, although I normally hurry on through the Race or Watch Hill Passage to Block Island . Block Island is a great destination, truly out to sea, with enough to do to keep everyone happy. The biking and hiking trails are great, plenty of good restaurants, super beaches, etc. Try to stay a few days if possible.

Everyone knows Newport , but Narragansett Bay offers a vast selection of Harbors, Jamestown , East Greenwich , Wickford , Bristol (visit the Herrshoff Museum), and the Kickamuitt River , where I spent a Hurricane a few years ago. All fine cruising grounds.

Long Island ties run deep for Cole Brauer, 1st US woman to sail around the world alone

By pei-sze cheng • published march 7, 2024 • updated on march 8, 2024 at 7:47 am.

Cole Brauer made history as the first American woman to sail nonstop around the world by herself.

The 29-year-old, who came in second in the Global Solo Challenge, is an East Hampton native. Her teachers at East Hampton High School watched her heavily documented journey with awe.

"It brings pride to the whole school and whole community,” said principal Sarah Smith.

24/7 New York news stream: Watch NBC 4 free wherever you are

"All the same things we are seeing with her now,” said video production teacher Jeremy Quitko, “Is what I saw in the classroom where she was on camera and also edited her own videos.”

Teachers and administrators remembered her determination and drive. She was voted most unique in the senior class, was on the track team, and a member of the Art Honor Society.

There was a sailing club at school, but ironically, Brauer did not participate — although her twin sister Dalton did. Brauer learned to sail when she lived in Hawaii, which kicked off a passion that she has been pursuing ever since.

Get Tri-state area news delivered to your inbox. Sign up for NBC New York's News Headlines newsletter.

Brauer set sail in October and sailed 30,000 miles, starting from Spain, down the west coast of Africa, to Australia, and around the tip of South America before returning to the starting point.

‘Cat Ladies Unite': NYC Halloween parade introduces a new theme with political undertones

The benefits of being a foster for stray cats

Brauer's 130-day journey was treacherous at times, facing 30-foot waves and hurricane-force winds. Cameras at one point showed how rough seas threw her across the boat, injuring her rib. Another time she was so dehydrated, she needed an IV, which she inserted herself.

On the TODAY show, she was asked how she managed to continue with the journey.

"There really is no option at that point you’re so far away from land, there is no rescue," said Brauer.

Adam Fine, the superintendent of East Hampton schools, used to be Cole’s principal and remembers a time when she stopped to help a stranger who got into a car accident.

“It was really indicative of her personality — there was no fear, somebody involved in the accident, she went over to help,” said Fine. “So when I watch videos of her putting in her own IV, I know she can handle these sorts of things.”

For current students who watched her journey, Cole is an inspiration.

“She obviously has the motivation and determination,” said sophomore Maya Taveras. “It’s nice to see her accomplish her goal.”

“It shows even if you come from a small town you can make a big impact on the world,” said Ryleigh O’Donnell, a senior, “Get your name out there and make a big difference.”

Celebrating Cole’s accomplishment has inspired administrators to recognize other graduates and their accomplishments.

This article tagged under: