sailing tours long island

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.

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With Captain Lou Fleet, embark on a memorable voyage from the iconic Nautical Mile in Freeport, Long Island, New York. Whether planning a lively party or seeking a private charter experience, Captain Lou Fleet is your ultimate destination for all boating needs!

Want to join us on one of our many fishing trips or specialty cruises click the button below to view our full calendar and book now.

Don't miss out on the exclusive 4th of July celebration with us!

We're excited to offer two different cruises! The first is a regular fireworks cruise on the Atlantic Pearl, featuring a DJ and cash bar for drinks and snacks, with a spacious open top deck, perfect for watching the Jones Beach Fireworks show. Additionally, we will have all-inclusive cruises aboard the Starstream VIII. This cruises will include an open bar, dinner with a selection of hot entrees, side dishes, salad, dinner rolls, dessert, and coffee or tea, as well as a DJ and dancing!

SPECIAL - Father's Day Cruise

Join us in celebrating Father's Day with a memorable cruise on the Captain Lou VII. Enjoy a scrumptious buffet along with unlimited beer, wine, soda, juice, and water. Groove to the live music of a DJ while taking in the breathtaking views. The cruise will take place on Sunday, May 12th, from 2:30 to 5:30 pm.

Discover everything about our fleet of boats and explore what's on our calendar and in season!

Make sure to always refer to our calendar to find out which dates and times are available.

Captain Lou VII

The 85' Spacious Super Cruiser features an expansive upper deck that is fully covered, offering a climate-controlled cabin for ultimate comfort. Additionally, it includes a generously spacious galley, ensuring ample space for your enjoyment and relaxation.

Current Available Trips:

• - 3/4 Day Fluke Trip
• With Captain Anthony Gillespie

• Starstream VIII

Step aboard our 100' spacious super cruiser, featuring a fully covered upper deck to provide shade and shelter. The beautiful newly renovated cabin offers a comfortable and stylish space to relax, while the galley ensures that all your catering needs are met. Whether you're hosting a party, event, or planning a fishing trip, this versatile vessel is the perfect choice for any occasion.

- 1/2 Day Fluke Fishing Trip

With Captain Willie Garris

Atlantic Pearl

Take a look at this incredible 100-foot all-aluminum super cruiser. It offers a spacious and perfect setting for sightseeing, various kinds of parties, and of course, fishing!

- Whale Watching Cruises

Please check our calendar CLICK HERE  

Please check our calendar for available dates and times.

Diamond Girl

Great for up to 6 people for private charters or fishing! Now sailing out of Freeport on the Nautical Mile. This beauty is great for engagements and small group gatherings!

Sapphire Princess

A modern luxury wedding/dinner Yacht designed and built for the purpose of hosting special events for up to 127 guests. The vessel is equipped with two full-service bathrooms, fine wood cabinetry, brass details, a full-service bar, a curved staircase leading to the second level, DJ booth, large dance floor, and two large outside areas with bistro tables and seating.

Limited or Special Fishing Trips with Captain Anthony Gillespie!

Embark on an unforgettable fishing adventure with our exclusive excursions, expertly led by the experienced and skilled Captain Anthony Gillespie!

Currently sailing trips: Limited - 3/4 Day Fluke Trips Special - 34-Hour Distant Canyon Trips Limited - 3/4 Black Sea Bass Trips (starting July 1st, now bookable)

Future Trips: Special - Offshore Codfish Trips Limited - Full-Day Ocean Wreck Fluke Trips Limited - Full-Day Blackfish Trips Special - King of Tog Tournament

View Calendar

Fishing updates.

Join us to stay informed about our latest fishing excursions!

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• Capt. Lou VII
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***Starstream VIII 100' Super Cruiser with Captain Willie Garris*** Are you looking for an exciting day of fishing? You've found it! Our experienced crew is ready to help you catch that big one. Even if you've never fished, we'll teach you everything you need to know and ensure you have a fantastic time. We are sailing every day 7 am - 12 pm and 1 pm to 5 pm! If you have any questions, please feel free to call us directly at 515-623-5823. To book a trip now, visit our website, www.captloufleet.com . We are at 31 Woodcleft Ave. Freeport, NY 11520. ***All photos are from the half-day fluke trips on 6/10/24 & 6/11/24*** ... See More See Less

• Comments: 0

0 Comments Comment on Facebook

Father’s Day Fishing on the Capt. Lou 7!! 9am to 1pm Plenty Of Room Available, book at www.captloufleet.com or call 516 623 5823 FLUKE!!! ... See More See Less

• Comments: 2

2 Comments Comment on Facebook

Great Captain and crew🎣🎣

Photos from David Leis's post ... See More See Less

Awesome catch! Congrats!

WOW GREAT TRIP ALL I HAVE TO SAY IS THAT THE ATLANTIC PEARL IS THE REAL DEAL GREAT JOB

***Starstream VIII 100' Super Cruiser with Captain Willie Garris*** 6/8/24 & 6/9/24 Captain Willie reported that the weekend fishing was active in the mornings, with some nice keepers. Join us for a half-day #fluke fishing trip on Long Island's South Shore. Bait and tackle provided. Special rates are available for seniors on Mondays, ladies on Wednesdays, and servicemen on Thursdays. Plan your fishing adventure as we sail every day from 7 a.m. to 12 p.m. and 1 p.m. to 5 p.m. If you have any questions, please feel free to call us directly at 516-623-5823. To book a trip now, visit our website, www.captloufleet.com . We are at 31 Woodcleft Ave. Freeport, NY 11520. ***All photos are from the half-day fluke trips on 6/8/24 & 6/9/24 *** ... See More See Less

• Comments: 11

11 Comments Comment on Facebook

Great catch👏🏻👏🏻

I MISS LONG ISLAND, just couldn't afford it anymore 🎣

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Want to charter one of our boats out for a private event?

The Captain Lou Fleet has the perfect boat for any occasion!

Private Charters

Our fleet has the right boat for any occasion!

For more information or to book a private charter Contact Us at [email protected] or call us at (516) 623-5823

Fishing Trips

Are you interested in chartering an entire boat for an incredible fishing excursion? No matter the size of your group, we have boats available to accommodate both large and small parties!

Birthday Parties, Special Occasions, and More!

Looking for an unforgettable way to celebrate your special occasion? Look no further than the Captain Lou Fleet located in Freeport, Long Island, New York! Whether you're planning a Sweet Sixteen party or a 50th birthday bash, we have everything you need to create the perfect event!

Corporate Events

Looking to add a unique touch to your corporate event? Our comprehensive accommodations are designed to ensure that your event is not only professional, but also an enjoyable and memorable experience for all attendees!

The Captain Lou Fleet is sailing around social media!

Keep up with all of our content and updates by following us on Instagram & Facebook

• likes wow 16

🎉Special Father's Day Cruise🎉 Join us in celebrating #fathersday with a memorable cruise on the Captain Lou VII. Enjoy a scrumptious buffet along with unlimited beer, wine, soda, juice, and water. Groove to the live music of a DJ while taking in the breathtaking views. The cruise will take place on Sunday, June 16th, from 2:30 to 5:30 pm. Secure your tickets now by visiting Captloufleet.com (516) 623-5823 | 31 Woodcleft Ave. Freeport NY, 11520 ... See More See Less

• likes love 11

Next “Off The Grid” BIG TILEFISH TRIP is JULY 7 Thru 10! Put yourself in the Video, NOT WATCHING IT Call 516 623 5823 only 9 spots left! ... See More See Less

This content isn't available right now

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• Comments: 1

1 Comment Comment on Facebook

How would you consider this trip ? Good Fair. Excellent? Just curious Thanks. Mike. M

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FRIDAY JUNE 14 (6:30 AM to 12:30) EARLY BIRD FLUKE SPECIAL! Capt Lou 7 Sunday June 16 SPECIAL 9am to 1pm FATHER’S DAY FLUKE!!! Capt Lou 7 Book at www.captloufleet.com or call 516 623 5823 Freeport NY ... See More See Less

• likes love wow 206
• Comments: 20

20 Comments Comment on Facebook

How do you find such huge ones wow.

EXCELLENT CATCHES

Wow Andy did you have to Throw any back !

Saturday June 8 DON’T MISS THIS!! 6:30 to 12:30. Walk On’s accepted for this trip! Light Crowd!! CAPT LOU 7!!! The FLUKE LIFE for our charter this morning is HOT & HEAVY!!! We have our EARLY BIRD SPECIAL tomorrow Sat June 8 from 6:30am to 12:30 31 Woodcleft Ave Freeport NY Book here: www.captloufleet.com or call 516 623 5823 tell them you want the 6:30am EARLY BIRD SPECIAL ... See More See Less

• likes love 34

🎇Don't miss out on the exclusive 4th of July celebration with us!🎇 We're excited to offer two different cruises! The first is a regular #Fireworks cruise on the Atlantic Pearl, featuring a DJ and cash bar for drinks and snacks, with a spacious open top deck, perfect for watching the Jones Beach Fireworks show. Additionally, we will have all-inclusive cruises aboard the Starstream VIII or the Captain Lou VII. This cruises will include an open bar, dinner with a selection of hot entrees, side dishes, salad, dinner rolls, dessert, and coffee or tea, as well as a DJ and dancing. To book your trip now, visit our website captloufleet.com! We are located at 31 Woodcleft Ave, Freeport, NY 11520 Call us at 516-623-5823 BOOK NOW: Captloufleet.com ... See More See Less

Check out our Partner Sites!

Long Island Whale & Seal Watching ,  Nautical Mile Cruises  & Ashes of the Seas proudly use The Captain Lou Fleet's boats for all our events and cruises!

Long Island Whale & Seal Watching

Experience the wonders of marine life just off the coast of Long Island. Join us at Long Island Whale & Seal Watching for an unforgettable adventure on one of our Whale or Seal Watching cruises, where you can witness nature's captivating beauty up close.

Check Long Island Whale & Seal Watching's Calendar for upcoming Whale Watching Cruises starting May 18th

Nautical Mile Cruises

Are you looking for a fun night out on the water? Visit NauticalMileCruises.com to view a full Calendar of all our Cruises!

The 2024 season is almost here!

Ashes of The Seas

We are experts in curating and arranging elegant Nautical Farewell Ash Scattering Cruises, providing a unique and dignified way to bid farewell to your loved ones.

[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. 

Oyster Bay is home to former U.S. President Theodore Roosevelt and is currently 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

From $1,395

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

“My husband and I booked a 3 hour sunset charter while on vacation in NY and were blown away by the natural beauty of Oyster Bay Harbor. Jonathan was a great captain - attentive and welcoming - he even taught us the basics of how to sail! The boat was beautiful - luxurious and comfortable. 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.

Book Sailing Now

• Catamaran Private Charters (up to 100 guests)
• Small Group Private Charters (1-6 guests)
• Corporate Events
• Free Children’s Sailing Clinics
• Soul Sailing With Captain David Ryan
• About the Mon Tiki Fleet
• Gift Certificates

Sail With Us!

The Mon Tiki catamarans—built by the people who sail them. Inspired by traditional Polynesian designs, our eco-conscious catamarans are the only US Coast Guard certified sailing vessels in Montauk and the largest on Long Island. Book a private charter and create your own special seafaring adventure. Enjoy a relaxing day sail, swim with our included SUP paddle boards, or take in a sunset cruise on the bay. Whether you’re a group of 1-100 passengers, we’ve got a catamaran adventure that’s right for you!

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

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Call Anytime

+12035127751

SAILING CHARTERS, SUNSET CRUISES, DAY SAILING

Sailing trips and charters.

LATEST NEWS: We have moved to a new location in New London Harbor now offering sailing trips to Fishers Island, the Mystic area and the Hamptons! You can even participate and learn basic sailing skills. Come and discover the beautiful scenery around New London, Mystic, Fishers Island and the Hamptons.  We provide 3 hours sailing time up to 6-7 hours. Something to remember and ideal for special occasions such as birthdays, family, friends gathering or corporate events. 

SUNSET CRUISES, DAY SAILING

Our sunset cruise  is the most popular sailing event. We usually leave the dock around 5pm to return around 8pm (flexible on weekdays). Bring your own drinks and food and treat yourself and your loved ones to an evening of sailing with a great sunset, good laughs and music. Sat-Sunday: up to 4 people, $650 for 3 hours Weekdays : up 4 people, $550 , $100 per additional person. Call or email to reserve your next sunset cruise!

WORLD SAILING ADVENTURES: CAPRI, AMALFI, PROCIDA, FRENCH RIVIERA 7 DAYS/6 NIGHTS CHARTERS

We now propose a wide range of world sailing adventures on luxury catamarams or on our 50′ Beneteau sailing yacht based out of Ischia, Naples Italy. Discover one of these beautiful sailing paradises. Groups of 6 people on luxurious catamarans with crew of 2 (skipper and cook). Stay tuned for dates and rates or contact: Eric: [email protected] or call Eric at +1 203 512 7751

SAILING COURSES ON YOUR BOAT OR OURS

You and your spouse may need help to get familiar with your sailboat like sail trimming, docking or basic boat maintenance. If you don’t yet have a boat, we offer a wide range of sailing courses, private or in groups tailored to your needs. Welcome to Sail Coaching!

SAILBOAT CONSULTING

Interested in buying a new or used sailboat but  can’t decide which one is best for your needs such as cruising, day sailer, size, family oriented, etc…? There are so many used saillboats for sale, the choice is difficult to make so save yourself time and money and use my 45 years of sailboat experience. I will guide you with the selection process and all the way to the closing negotiation and sale.  I can also provide sailing lessons and advise on improvements or repairs if needed.  Contact Eric: [email protected]

Watch our Videos

Fisher's Island, NY

Sag Harbor, NY

East Hampton, NY

Sail-works CT sailing cruises

Our picture gallery. your memories..

We strive to make your time spent on Nomade a special moment with unforgettable memories. Over the years, we captured those images for you to enjoy and share.

• Sunset Cruises
• Sailing trips
• Sailing Instruction
• Boat services

SECURE YOUR SAILING CRUISE

$200 deposit will secure your sailing cruise, 100% refundable in case of bad weather. Balance to be paid before sailing cruise ends. 10%-15% gratuity is not included and always appreciated. After this transaction, you will be redirected to our Contact Page. Thank you.

NOTE: You can also use VENMO (no fees): Send deposit to: @Eric-Treu-1

Come sailing with us, we make it easy and fun !

• Quick Links
• Sailing trips and charters
• Sunset cruises, day sailing
• Sail Coaching on your boat
• Official Info
• Thamesport Marina 260, Pequot Avenue Slip South Dock S44 New London Connecticut 06320 United States
• +1 (203) 512 7751

Stay in touch with our promotions and new travel destinations by joining our Newsletter. Thank you!

Copyright © 2024 sail-works.

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

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Complete with a captain and hostess, our service will provide a luxurious experience for personal trips, family excursions, and special events.

Rent a Luxury Yacht for a Personal Cruise or Private Party

Cruise the long island sound in luxury.

Grab your friends and family, sit back, relax, and enjoy a “personal cruise” or “private party” on the Long Island Sound in Style! You can even bring your own food, snacks, drink, and alcohol, and the boat will be “exclusively” yours!

Charter Boat Rentals Around Long Island, NY

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Every event is custom tailored to your unique experience. The boat is “Exclusively” yours. You can pick and choose the events your group wants to do. It starts with a slow chartered cruise exploring the Long Island Sound, scenic drives past ports & beaches, anchoring in a private cove where you can swim, relaxing on our inflatable islands and so much more.

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At Long Island Private Yacht Charters, we offer private charter excursions touring the “Long Island Sound” on the beautiful 459 Meridian Motor Yacht.

Long Island Private Yacht Charters

Phone : 631-648-8055

Website :   www.lipyc.com

Email : kevin@lipyc.com

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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.

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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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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!

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

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.

THE 5 BEST Long Island Boat Tours

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1. Boat or Yacht Rental in Sag Harbor, The Hamptons, or Monatauk

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Long Island Sailing

Sailing has been a Long Island pastime for centuries, and the popularity of the sport won’t be slowing down anytime soon. Surround by the Long Island Sound and the Great South Bay, it is no wonder why this water sport is a favorite of both locals and visitors alike – not only is it fun to sail, but enjoying the beauty of sailboats is an experience that spectators on the shores of Long Island simply can’t pass up. Whether you’re new to sailing, and simply looking to get some lessons as you gain your sea legs, or you’re an old ... Read More Sailing has been a Long Island pastime for centuries, and the popularity of the sport won’t be slowing down anytime soon. Surround by the Long Island Sound and the Great South Bay, it is no wonder why this water sport is a favorite of both locals and visitors alike – not only is it fun to sail, but enjoying the beauty of sailboats is an experience that spectators on the shores of Long Island simply can’t pass up. Whether you’re new to sailing, and simply looking to get some lessons as you gain your sea legs, or you’re an old pro looking to upgrade your boat, there are local marinas and sail boat specialists here on Long Island that can get you out on the water in no time. Show Less

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Oakcliff Sailing Center

4 South Street in Oyster Bay 516-802-0368

Sag Harbor Sailing

51 Pineneck Ave in Sag Harbor (631) 725-5100

Sail Long Island

Brewer Yacht Yard in Greenport 917-912-6342

SailTime Long Island

90 Colonial Drive No. 2 in East Patchogue (877) 724-5846

The WaterFront Center

1 West End Avenue in Oyster Bay (516) 922-SAIL

Want to be added to the Sailing Page? Call 631-406-4410 or Email Us for details!

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Long Island Boat Tours To Help You Enjoy Our Beautiful Island

Long Island boat tours are one of the best ways to explore this beautiful part of New York. Most of us might think of boat tours as something reserved for tourists. However, they’re actually an amazing way to take in all the beautiful sites of Long Island for locals, as well. After all, none of us have seen everything our areas have to offer. It’s always a good idea to see things from a different perspective. Plus…we’re an island, we might as well take advantage of it, right?!

Long Island Boat Tours: A Must

Whether you’re visiting the area or a long-time local, Long Island boat tours are one of the best ways to really experience the beauty of this often overlooked part of New York, right outside the hustle and bustle of NYC. Below, you’ll find a list of the best Long Island boat tours to be found in the area. They’re all waiting to show you and your family an amazing time and amazing views.

Layla Sailing – Shelter Island

Explore all the beauty and views that Shelter Island has to offer with Layla Sailing. You can choose from half-day charters or shorter morning and sunset sails. Captain Liz Gillooly will take you and up to five other passengers on a private sail trip that explores the best of the area.

Find out more by visiting laylasailing.com or by calling 631-319-0161.

Christeen – Oyster Bay

Adventure out and tour Oyster Bay on the Christeen, a restored oyster sloop. The trips are offered through The Waterfront Center, and reservations must be made online. You’ll be able to choose from a two-hour harbor tour or book private charters for your group. Throughout the tour, you’ll see Gold Coast mansions on Tony Centre Island, all captained by a Coast Guard-certified operator. You’ll also take in amazing views as you learn about the history of the area, including Christeen, a National Historic Landmark built in 1883.

Find out more by visiting thewaterfrontcenter.org or by calling 516-922-7245.

Sailing Montauk – Montauk

Explore the Montauk area with Sailing Montauk’s fleet of Mon Tiki catamarans. Owned and operated by Amelia Ryan and her husband, Captain David Ryan, Sailing Montauk offers cruises on the 65-foot Mon Tiki Large, the 40-foot Mon Tiki, and the 26-foot Mon Tiki Mini catamarans.

Bring your own lunch and drinks for a two or three-hour private sail that offers views of the area’s coastline, waves, and sealife – watch out for dolphins! If the weather is warm, you can even enjoy a nice dip in the ocean.

Find out more by visiting sailingmontauk.com or by calling 631-668-2826.

Priscilla – West Sayville

Venture out on a restored 1888 oyster sloop called the Priscilla to enjoy amazing views of the Great South Bay. Offered by the Maritime Museum in West Sayville, the Priscilla takes visitors out on two-hour cruises on the Great South Bay. Enjoy all the narration offered by the captain as they teach you about the ship’s history as part of a 500-boat fleet that once scoured the South Shore bays for oysters.

Find out more by visiting limaritime.org or by calling 631-854-4974.

See Things in a Different Way with Long Island Boat Tours

Long Island boat tours offer something a bit unexpected for both visitors and locals, alike. A tour on any of these boats is full of history, beautiful views, and tons of family memories that will last a lifetime. Book a tour with any of these, and see Long Island in a completely new way.

More From The Long Island Local

Maybe grab a freshly brewed beer at these  Long Island breweries !

And how about all the wonderful  Wölffer Estate Vineyard  events and tastings?! Or maybe check out some  Long Island oyster farms ! How about these guides to  Long Island Coffee Shops  and  Long Island coffee  roasters!! Check out these 16  Long Island Boardwalks ! Take the ferry over and enjoy these  Fire Island restaurants ! Let’s not forget about the  best tacos on Long Island  and these 32 great  Long Island pizza  places either!! Here are 21 great spots to enjoy  Long Island Gelato !

Be sure to find out about more  things to do on Long Island  as well as more great spots to  eat and drink ! Maybe take a stroll in one of these amazing  Long Island arboretums  and gardens! There are even this great Long Island kayaks and paddleboard guide to exploring!

Long Island Farm Guides To Explore

Suffolk County agriculture includes over 560 farms with 4,600 people that generate more than $226 million in sales annually. Long Island knows farming as well as  Long Island farmland preservation !! How about enjoying some wonderful  Long Island hiking  trails!

Check out more  Long Island Farm coverage  on The Long Island Local!

Explore our Guide to  organic farms on Long Island  and our  Guide to CSA on Long Island .

Read about great events like the  Tulip Festival at Waterdrinker Farm  and all that the  Golden Earthworm  has to offer!

What about this massive list of  Long Island farmers  and farms you need to visit!

How about  Long Island Oyster Farms , the last  Long Island Duck farm , or the only fresh American snail farm  Peconic Escargot !

When the season’s right, explore our  Long Island Christmas Tree farm  guide and our list of great  Long Island pumpkin picking  farms!

Check Out Long Island Wine

If you’re in the mood for great wine, be sure to check out our  Complete List of Long Island Wineries  and Long Island Vineyards.

Check out the absolute best  Long Island Wine Tours !

If you can’t make it to a tour, why not do some  wine tasting at home  with Bedell Cellars!

I know you’re getting hungry, so be sure to also check out the  best wineries on Long Island  for some great food!

While you’re in the area, be sure to check out these 9 relaxing  things to do in the North Fork !

When you’re done with all of this wine drinking and relaxing, how about making it a weekend? Here are 10 great  North Fork Long Island hotels  to enjoy as well.

Things To See and Do on the South Fork

I always recommend seeing as much of the South Fork as possible!! 

The Hamptons  and Montauk is a world-renowned beach resort destination for good reason! There is just so much to see, do, and enjoy! Here are just a few of them:

Check out this Guide to the  Best Beaches in Montauk ! Also, check out this Guide to The  Hamptons best beaches !!

Check out some  luxury homes in The Hamptons !

Maybe you will love it so much, you’ll want to check out some  Hamptons wedding venues !

Enjoy some of the world-class, amazing  art in The Hamptons !

While You’re Enjoying the Outdoors

Be sure to find out about more  things to do on Long Island  as well as more great spots to  eat and drink  and wonderful  places to stay  on Long Island!

Check out this guide to  Long Island driving ranges , including this feature on the popular  Heartland driving range ! Go have fun at one of these great  Long Island skate parks !

Make It A Weekend

The East End of Long Island is a really special spot. If you think you’d want to check it out and maybe even stay a while…that wouldn’t be such a terrible idea.

If you wanted to consider different options for staying on Long Island, be sure to check out these great  places to stay in Montauk , 11  Hamptons hotels , 10  North Fork Long Island hotels , and this Guide to  Sag Harbor hotels ! Enjoy reading up on and hopefully exploring these wonderful  Shelter Island hotels  and let me know if you decide to make it a vacation!

Tulip Festival at Waterdrinker Long Island

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Guide to Long Island Apple Cider Donuts

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