sailboat charter long island

[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, subscribe for updates & promotions.

©2024 Windward Sailing Charters, All Rights Reserved.

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

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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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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

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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

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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!

SWITCH VESSEL

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

Packages Options

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.

HAVE ALL DAY?

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

Terms & Conditions

All Rights Reserved | Long Island Private Yacht Charters  © 2024

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.

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]

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Sailing evening cruises on L.I Sound

Fisher's Island, NY

Sag Harbor, NY

East Hampton, NY

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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

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Welcome! Experience Long Island Sound aboard Yacht Sequester

This Is Way More Than a Cruise

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take a virtual tour of our boats

Charter rates.

The Best Sailing Vacation in New England at your Fingertips .

Charter begins Friday at 5:00 pm and finishes on a Friday by 11:00 am. Prices include 10’ dinghy w/ motor, insurance, tax, 8 pillows, bath towels & bottom linens. You bring food, drinks, ice, toilet paper, paper products & top blankets/sleeping bags. Captain or sailing instructor can be added at $3,000+ per week.

• Moorings and dock space: We recommend downloading DockWa. Visit their website (or download the app) to book. Also, some harbors are ‘first come…first served”
• Check out our Google Earth Map & Chart. Choose from one of our charter boats below. For more information on sailing in the Newport RI area, call or email us today!

Over 75 sailing destinations within 75 miles of Newport.

AVAILABLE CHARTERS

Now taking reservations for May, June, July, August, Sept. & Oct. 2025 charters.

Google Maps Harbor Views

Check out interactive maps of New England’s harbors.

Early May, late-Sept. & Oct. weekend or mid-week special 2-day rate starting from $2,000. Additional days can be added at $700 per day during early May, late-Sept. & Oct.

contact us to schedule your private showing. -->

Testimonials

We booked a sailboat with a local Massachusetts broker and were informed a week before the charter that the sailboat was not available and she had no replacement. We were highly disappointed as my dad, brother and father in law were flying in from across the country to sail for a week. I went on-line and found Bareboat Sailing Charters-Newport. Brian was most accommodating and a pleasure to work with. He was able to offer us a Jeanneau 49’ Deck Salon. The boat was well equipped with many options that included (3) color GPS chart plotters and a 10’ dinghy. The 20 minute virtual tour video of the boat was great and allowed us to get familiar with the boat and its systems prior to beginning of our sailing adventure. We now have wonderful memories with my family sailing to the islands of Cuttyhunk, Martha’s Vineyard & Nantucket. Looking forward to our next charter with Brian @ Bareboat Sailing Charters. Many thanks from Alex and family!! Alex

My husband and I chartered a Beneteau 45′ for a week long trip to MV and Nantucket, and hired Captain Scott. We own the same boat on the Great Lakes and wanted to get experience sailing in New England. Our boat was clean and in tip-top condition. Scott was an invaluable instructor and our navigational skills improved immeasurably. The entire experience exceeded our expectations (sun every day helped!) I would not hesitate to recommend Bareboat Sailing Charters. Tracy

We have chartered many, many times (since 1985) from Bareboat Sailing Charters in Newport. Great boat with great weekly charter prices. The boat was well maintained and all systems were highly functioning. The boat was well equipped with many options that included (2) color GPS chart plotters and a 10’ dinghy. The 20 minute virtual tour video of the boat was great. After watching it, you feel like you already know the boat and its technology upon boarding. Thanks, Bareboat Sailing Charters for a memorable vacation! Daniel

A dream come true for Captain and crew! The Jenneau 439 we chartered from Bareboat Sailing was comfortable and perfectly suited for our group. The boat was well equipped and in great working conditon when we boarded. We spent the next 6 days bopping port to port around the Elizabeth Islands and Martha’s Vineyard. Bareboat Sailings crew made everything easy for first timers in that area. We’ll be back next year! Chip

“What a fantastic vacation”. We just returned from a wonderful vacation aboard the Beneteau 45 we chartered. There were two families onboard, but with 4 cabins there was plenty of room for everyone. The boat was equipped with all the electronics we could need and the chart plotter was especially useful during our week. The best part of the boat, according to my kids, was the hydraulic transom that lowered to create a great swim platform. Will charter again and again. Wendy

We rented July a Jeanneau 439 for 3 weeks to sail from Newport to New York and back. This long dream became really true. And thanks to Brian we were excellent prepared by several books, maps and most important by a super maintained ship equipped with everything we needed. I charted already boats all over the world, but here both the check-in and check-out was the easiest and fastest ever. Thanks for this great time! Karl

“Living the Dream!” My friends and I just booked our first charter with from Bareboat Sailing Charters to Nantucket last week. The boat was well maintained and all systems were functioning. The boat was well equipped with many options that included (2) color GPS chart plotters and a 10’ dinghy. The 20 minute virtual tour video of the boat was great. After watching it, you feel like you already know the boat & electronic when you board. Chalk up another great sailing vacation!!! John

This is my 5th time chartering through Bareboat Sailing. The boats are the best maintained of any I have chartered and I have been doing this for about 12 years. The checkouts and support from Brian and his crew are second to none. The boats are very well equipped, including chart plotters and radar. They also come with a dinghy and outboard. Like the boats they are always in good order…not necessarily a given in the charter industry. Simply put, Bareboat is one of the most professional organizations I have dealt with and I look I forward to many more trips with them in the future. Al

This outfit and the people behind are absolutely fantastic. I have chartered from them every year for the last 10-years and each time my expectations are far exceeded. The boats are always in excellent condition (with a noticeable and very well received emphasis on safety), the service and help we get along the way from Brian and his staff always goes above and beyond, and the area / region is not to be beat. You are virtually guaranteed to have a terrific experience if you choose Bareboat Sailing Charters. Ross

Kick back, relax and enjoy the 'Tranquility' of your charter with Captain Jeff Sellars

Tranquility

Experienced staff.

Join us on our 50-foot Carver with three bedrooms, a modern motor yacht with a sprawling interior layout including a salon that seats 12. Offering plenty of room to enjoy your charter.  We spared no expense and splurged on all of the luxuries expected. 

Captain Jeff is a seasoned boat enthusiast who is passionate about providing you with the best possible boating experience. His vast knowledge about the local waters makes him an expert in his field.  Captain Jeff and his talented staff are happy to offer helpful tips and advice to make your charter a memorable experience.

Water Amenities

Water activities include 2 stand-up paddle boards, a 2-person kayak, masks and snorkel's, sea scooters, a floating island, a floating doc perfect for tanning, a four-person towable tube, an on-board BBQ, with a smaller RIB boat to be used as a tender, or for rides.  

Enjoy the gold coast summer and book your charter today!

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Long Island Yacht Charters

1 West End Avenue, Oyster Bay, New York 11771, United States

516-680-6787 [email protected]

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SAG HARBOR SAILING

Rentals, lessons, charters and summer youth programs, explore sailing lessons, rentals and youth programs, sail the hamptons, home to some of the world's most beautiful waterways, sailing boat rentals.

Our 23-foot Pearson Ensign sailboats can comfortably accommodate up to six people. Whether you choose to sail with a captain or on your own, you can fully enjoy your time on the water.

Additionally, our Commodores Club offers seasonal savings for those who sail more than three times.

LEARN TO SAIL

Our instructors offer private lessons on our company’s fleet of 23-foot Pearson Ensign sailboats. Each private lesson can accommodate up to four students, ensuring personalized attention and effective learning.

Get certified with our 2-day American Sailing Association beginner sailing certification program.

SUMMER YOUTH PROGRAM

Our week-long program features a wide range of activities on the water including sailing, wake boarding, tubing, water skiing, learning to captain a boat, fishing, paddle boarding, SEABOBS, swimming and more.

Sessions are held Monday–Friday, 9–12:00pm for ages 9–16 and operate from July 1 to August 30. Sign up for multiple weeks or just for the day.

TWENTY YEARS OF SAILING IN THE HAMPTONS

"We had a great day out on the water! The boat was in awesome shape and the staff were super helpful!"

"We rented a sailboat on Sat. Beautiful day. Captain Mark was great and let us be hands-on as possible sailing the 23 ' Pearson Ensign. Would recommend highly!"

"My wife, 2 boys and I hired Mark for the sunset cruise. He was great, the weather was beautiful and our evening was perfect. I highly recommend."

"Great trip fishing with captain Bob! He was great with kids. Two hour fishing trip is just right."

THE SAILING YACHT NIRVANA

A Private New York Yacht Charter

No crowds, just you and your closest friends on board this classic beautiful 38 foot sailboat with her U.S. Coast Guard Licensed Captain/Owner. We sail out of breathtaking Mamaroneck Harbor, New York, and go to a destination of your choosing or wherever the wind takes us. You can take the wheel and trim the sheets or just lie back and enjoy the sun and gentle breeze. We offer full day Yacht Charters, romantic sunset cruises, or longer trips. It's all up to you.

To Charter Nirvana

Call: (845)803-5104 or

e-mail: [email protected]

www.charternirnana.com

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Frequently asked questions

Do you need a boating license to rent a boat in Long Island,NY?

Yes, in Long Island, NY, the state mandates a boater education law for certain operators of boats and/or personal watercraft. For specific boating safety course requirements, visit the New York State Parks official website (http://www.parks.ny.gov/recreation/boating/). Additionally, considering booking a rental or charter with a captain is a seamless option Boatsetter offers for Long Island and various other locations. Ensure to confirm any additional requirements with local owners and operators.

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Boat and yacht rental prices in Long Island vary based on boat size and rental duration. You can rent a boat for $56/hour.

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Long Island, NY experiences average water temperatures ranging from around 40°F in winter to approximately 75°F in summer.

Everything was awesome from start to finish !!! The owners the captain, everything was amazing!!!

The ONLY 40-ft...

Absolutely fantastic time on the Hudson. Boat was way cooler than we were expecting. Captain was so warm and...

HUNTER LEGEND 35...

46 foot fully...

Enjoy Fire Island...

Neal & Jacob were the best of the best! To notch class acts and fulfilled my expectations to the fullest! Highly...

Captain Andy was a very welcoming and gracious host. He accommodated my guests and I on such short notice, with full...

Had an amazing time! Marco was terrific! Made the evening absolutely amazing!! Great talk and accommodation!!

TRAVEL IN LUXURY...

Responded promptly and communicated well to get us out and on the water to enjoy the afternoon!

Day in the sun:...

We had a wonderful time. Lexington communicated with us leading up to the event and answered any questions we had . ...

Key West 203 Dual...

Great Value. Shawn and his sons were polite, informative and professional. The boat was just perfect for a day on the...

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Five Sailing Excursions to Take on Long Island

Sports & Recreation , Travel & Local Attractions

By Lon Cohen Published: June 22 2021

Book a fun day on a sailboat on the waters around Long Island.

The Ginny Marie Schooner. Photo: The Ginny Marie Schooner Facebook page.

Most people think of sailing excursions when they’re vacationing on a tropical island somewhere but there are plenty of places to hop aboard a sailboat to enjoy a day on the water right here on Long Island. Below we found just five of the many sailing charters you can book close to home.

Nautical Dreamer Sailing Charters - The Nautical Dreamer II is a Beneteau 50 sailing yacht that leaves out of Greenport Harbor. Choose from full day to 2-hour cruises. Overnight stays, weekends, and custom trips are also available. Location: Brewer Yacht Yard, Greenport Harbor, (631)767-0149.

Sailacat - A catamaran, Sailacat's charter boat offers private sail charters, sunset sails and boat tours in Historic Sag Harbor. Available for 4-hour sails with a beach break and swim time on weekends. They offer 2-4 hour sails midweek. Location: Sag Harbor, (631) 682-8288.

The Ginny Marie Schooner - The Ginny Marie is a 38’ wooden schooner that goes out of Port Jefferson Harbor. It’s historic, old world sailing that is a little romantic and a lot of fun. She can take up to 6 people on private charters that run 10am, 1pm, 4pm, and 6pm daily. Location: Harborfront Park, Port Jefferson, (631) 223-9180.

MTK Cruises - Offering three different vessels, MTK Cruises has Tomoka, a 40’ pontoon boat and two 27’ sailing catamarans, the Eleanor’s Pearl and the Calvin John. The pontoon can accommodate up to 33 people and the catamarans up to six. Each vessel can go to their 20’ water trampoline for a private gathering on the water or just cruise and relax. Location: 59 Star Island Road, Montauk, (631) 668-8079.

Layla Sailing - A 45’ sailing yacht available to take private charters of up to six people at a time. They offer morning, half-day, full-day, and sunset sails. The Layla is female owned and operated by Captain Liz. Location: 1410 Manhanset Ave, Dock H4, Greenport, (631) 319-0161.

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Long Island Yacht Charters

Long Island- Your Way!

Looking for a private yacht charter out of Long Island? Yacht Charter Group has a fleet of yachts, party boats, sailboats, and catamarans in Long Island. Our Long Island yacht charters are great for weddings, corporate events, parties, and vacations. Let our Executive Concierge help you plan your perfect outing, from choosing the right yacht, dinner menu, drink selection, and entertainment options. We pride ourselves on service and attention to detail. Imagine a cruise on a pristine ship, with a polite, professional, and attentive crew as well as personal chefs to attend to your every need and desire.

Yacht Charter Group has many embarkation points in New York, including New York City, Sag Harbor, South Hampton, East Hampton, and Port Washington. Depart from the World’s Fair Marina in Queens and see New York’s gorgeous bridges, see the Statue of Liberty, and gaze at New York City’s beautiful skyline, all from the comfort and luxury of your very own yacht.  Wherever you want to go, and whatever you want to do along the way, we are committed to making your dream vacation, wedding, or event a reality.

Yacht Charters Long Island

Let us show you the difference that over 43 years of experience in event planning and yacht charters makes! Experience the service and luxury of Yacht Charter Group, New York’s premiere private yacht rental service. We will stop at nothing to help you realize your dream cruise experience and cater to your every desire. Call 877-752-5001 to talk to your own personal assistant and plan your cruise today.

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Trip duration, multiple days (less than 1 week), weekly trip show boats that have weekly prices. most weekly boats outside of the us are available only saturday to saturday., boat length: 5ft -, manufacturer, boat build year: -, weekly trip, price: $ - $, 142 boat rentals in huntington, ny, usa.

In addition to the best offers we have for boat and yacht charters in Huntington, NY, see also options available for rent in these nearby locations:

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Choose a Long Island Boat Rental from Sailo to visit Bay Hills, NY

This summer you have to visit the Huntington Bay - a charming region on the North Shore of Long Island, home of Bay Hills - one of the most popular beach resorts in Suffolk County.

It’s time to leave the stress behind and take the well-deserved sailing trip with your family. Sailo offers an top selection of boat rentals around Bay Hills NY, perfect for a family vacation, a corporate event, a romantic getaway or private parties.

With a beautiful Long Island boat rental from Sailo you will have a relaxing but adventurous day on the water at the same time. Boating enthusiasts recommend visiting Sand City Island, a great place to swim, sunbathe or just relax aboard. Finish your day with a quick snack and a cold drink at one of the many waterfront taverns in Bay Hills Beach.

Choose a Long Island boat rental with captain and have a luxurious sailing experience in Northport Bay You cannot go wrong with a boat rental to explore Bay Hills NY and the Hungtington Bay, either a comfortable sailboat or a fancy motor yacht – it is guaranteed that your sailing trip will be a one of a kind experience.

If you plan to explore other nearby locations, then Oyster Bay has to be on your list. 

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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.