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Popular Sailing, Catamaran & Gulet Tours Charters in New England  , United States. Good availability and great rates. Read unbiased reviews and choose the best deal for your trip.

Sailing, Catamaran & Gulet Tours in New England- BoatBooker

New England

New England, United States

new-england

Enjoy a 3-hour sailing adventure aboard Tandemeer, our 60-foot luxury Ketch, exploring Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound. Feel the wind in your hair, take in stunning views, and dive in for a swim whenever you like.

Charters can start at any time between 10 AM and 4 PM—just give us a call to schedule your preferred departure.

United States

Island Sailing Tours

Martha's Vineyard

Set sail on the beautifully restored 1980 Nautical Development 56 Sailing yacht, refreshed in 2024, and based out of picturesque Martha&#039;s Vineyard. Accommodating up to six guests, this classic sailing vessel combines timeless charm with modern comfor

Set sail on a 2-hour eco-friendly sailing adventure from Westbrook, CT, where the scenic Long Island Sound becomes your playground. Glide silently across the water as you learn about local marine life and coastal ecosystems, with the chance to spot seabirds, seals, and more.

Joyride Charters

Westbrook

Come Sail with Captain Joy! Looking for an unforgettable experience on the water? Step aboard with Captain Joy &mdash; a USCG Master Captain with 40+ years of sailing adventures across the globe. Now docked in Westbrook, CT, she&rsquo;s ready to share the

Sail Long Island's Gold Coast on WINDSWEPT, a beautifully kept Jeanneau 36i! Private sailing charters can accommodate up to 6 guests. Departure times are flexible - select a start time that works best for your group!

Two-hour charters allow enough time to sail to the mouth of Oyster Bay Harbor and back. Perfect for catching a sunset or for touring the harbor, you'll have great views of the sandy bluffs and waterfront mansions that line the bay.

Windward Sailing Charters

Oyster Bay

Sail Long Island&#039;s Gold Coast aboard a beautifully maintained 2012 Jeanneau Sun Odyssey 36i. Moored in Oyster Bay Harbor, she features a large shaded cockpit with cushions and ample room for 6, a secured deck with double lifelines and USCG-approved s

This is a four-hour sail around the bay. This will allow ample time for a mix of sailing, swimming, exploring, and byob/food dining. We can cater to your desires and make a custom itinerary that 

works for you and your guests.

Martha’s Vineyard Charter Company

Set sail around the scenic waters of Martha&rsquo;s Vineyard aboard Our Passion, a beautifully maintained 1983 Pearson 422 Sailing Yacht operated by Martha&rsquo;s Vineyard Charter Company. Departing from charming Vineyard Haven, this classic sailing vess

Enjoy the world-class sailing grounds of Buzzards Bay and the picturesque coastlines of Dartmouth, New Bedford, and Fairhaven, Massachusetts. Whether you want to hoist the sails and take a turn at the wheel, or simply sit back, relax, and enjoy the harmony of sail and sea, an excursion on Omoo will be the highlight of your day.

Buzzards Bay Yacht Charters – Pearson 35

New Bedford

Buzzards Bay Yacht Charters offers unforgettable private day sails aboard a beautifully maintained 1979 Pearson 35 sailboat, based in New Bedford, MA. Perfect for couples, families, or small groups, this classic sailing yacht accommodates up to 6 guests, 

Set sail on an unforgettable 8-hour Mamaroneck adventure, where your departure time is completely up to you. Enjoy a relaxing sailing tour filled with scenic coastal views, a fresh sea breeze, and plenty of time to unwind or explore at your own pace. Whether you’re looking to soak up the sun or simply cruise in style, this flexible experience is tailored to your perfect day on the water.

Charter Nirvana

Mamaroneck

Step aboard Nirvana, a timeless 38&rsquo; Pearson 386 sailing yacht, and experience the beauty of Long Island Sound without the crowds, just you, your guests, and the open water. Departing from scenic Mamaroneck Harbor, your private charter is fully custo

A 6-hour private sailing experience in the protected waters of Narragansett Bay.

Catamaran Quest

Newport

Catamaran Quest is a beautifully restored 1991 Custom Simonis 57 Catamaran (refit in 2022), based in Newport, offering the perfect platform for unforgettable days on the water. Designed for comfort and stability, she accommodates up to 12 guests, making h

All our trips can be customized! The base price is $200/hr with a 3-hour minimum. If you'd like to sail for longer or start at a different time, just let us know.
Enjoy sailing through New York City waters with stunning skyline views of Manhattan, the Statue of Liberty, and the Brooklyn Bridge. Perfect for sunset cruises (depending on timing), swimming stops, relaxing sails, and unforgettable proposal & engagement trips. Bring your own vibe- romantic, fun, or chill- and we’ll make it happen on the water.

North River Sailing –  Tantara

New York City

We&rsquo;re setting sail across Long Island Sound this season from our home base on historic City Island. With its network of islands, lighthouses, sheltered harbors, and classic coastal towns, this area offers one of the most scenic and rewarding sailing

Set sail with us on your two-hour private sailing charter of New York Harbor. Your boat tour will take in the sights of the Statue of Liberty, Ellis Island, Governors Island, and the Freedom Tower, to name a few. Our daytime boat tour is ideal for visitors to NY, friends to enjoy an outing, or families looking for something off the beaten path to enjoy in New York City.

Tribeca Sailing

Step aboard Tribeca Sailing, a beautifully restored 1964 Hinckley Pilot 35, and experience New York City from the water aboard a true classic. Combining timeless craftsmanship with modern comfort, this elegant sailboat accommodates up to six guests and of

Sunsets,  celebrations,  or just a get away.
USCG Licensed Captain with a lifetime of sailing experience and  local knowledge to plan a great trip from Stamford, CT.

Want to get out on the water? 

Custom arrangements can be made - just ask. 

?Come sail away!?

Gypsy Soul Tours

Stamford

Gypsy Soul Tours offers private, custom sailing charters from Stamford, Connecticut, delivering unforgettable experiences on the scenic Long Island Sound. Step aboard a beautifully maintained 2005 Beneteau Oceanis 373, a comfortable and spacious sailing y

Sailing, Catamaran & Gulet Tours in New England

Top Sailing, Catamaran & Gulet Tours in New England