We provide the best cruises and flotilla trips.

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Set sail with American Sailing aboard various mega-yachts located around the world. Find amazing cruises in New England, The British Virgin Islands, Greece, and Croatia. Feel the wind, make new friends and explore multiple ports!


Why Sail with American Sailing?

We are not a travel Company. We are a sailing education organization that loves to sail.

We Want To Sail

Our goal is to get more people out on the water. We want you to go sailing. We organize these charters to expand our member’s ability to experience the joy of sailing. Therefore, we work to make these trips as affordable as possible.

We Are All Sailors

We are an organization of sailors. American Sailing is the largest sailing education entity in North America. When you sail on one of our member events you will be with other sailors.

We Teach Sailing

We are not a travel agency or a charter company. We teach sailing. We encourage you to use the skills that you learned while obtaining ASA certifications.  These are pleasure cruises but you will be surrounded by sailors and by people who love the water.

We Answer Your Questions

When you book there is one person handling your trip. One. You are not just another passenger, you are one of our members. Go ahead and send an email to zeke@americansailingvacations.com and you’ll see that your travel questions will be answered. 

We Sail With You

Whether you are sailing in New England, the British Virgin Islands, or in the Mediterranean, you will always have an American Sailing Ambassador on your trip to help with the details. 

Explore Croatia aboard Cataleya A Luxury Cruise

American Sailing
Availability : May 2024 / Sep 2024

Welcome aboard Cataleya a 30 meter luxury sailing yacht which will be your home for 8 days as you explore the Dalmation coast of Croatia. This trip will include stops in Split, Hvar, Korcula as well as a few anchorages that are the secrets of the captain and the crew. Join us on a once-in-a-lifetime sailing vacation.

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Greece, Mediterranean A Guided Flotilla

Fair Winds Sailing
Availability : June 8-15, 2024

Join American Sailing and Fairwinds Sailing Greece on a journey from Corfu through the Corfu Islands. Our local captains from Fairwinds Sailing will take us to their favorite anchorages and introduce us to Greece as seen through their eyes. Corfu Island is in the north Ionian Sea, between Italy and Greece (Greek “Ιόνιο Πέλαγος” – Italian “Mare Ionio”). Corfu is considered one of the finest and most cosmopolitan islands in the Mediterranean. 

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Lenny Shabes Sailing Festival ~ BVIs A Guided Flotilla

American Sailing
Availability : June 16-22, 2024

Join us for a week of sailing in paradise, as our late founder Lenny Shabes, set out to teach aspiring sailors to do. To pay tribute to all Lenny has done for the world of sailing, we are calling all sailors to partake in a week of festivities ranging from sundowners to regattas in the beautiful BVI’s.

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Arabella Grand Tour of New England A Luxury Cruise

American Sailing
Availability : August 2024

Arabella is one of the most beautiful sailing yachts in the world. She epitomizes classic elegance and graceful style and has been an icon along the East Coast in summer and in the Caribbean in winter. Arabella is also US Coast Guard certified, one of the few mega yachts with this designation in our country.

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  • “Everything is taken care of. You don’t have to worry about anything. You just sit back and enjoy the beautiful scenery, fresh sea air and fantastic ports of call to explore. In a very short time, we all got to know each other and everyone felt like family to me. I learned a lot, and enjoyed sharing this brief moment in time and space on this lovely boat called the Arabella.”


    Tracy Kosbau
  • “What do a film producer, a tech consultant, a dad and his son have in common with a group of Puritans? They all boarded a boat named Arabella bound for Massachusetts, albeit 385 years apart. Unlike John Winthrop and crew the modern passengers sailed in comfort on an ASA sponsored voyage to Martha’s Vinyard, Nantucket and Cuttyhunk islands!”


    Tim Shuman
  • “Absolutely no better way to relax… A full day of sailing aboard the “melts my heart” Arabella, lobster for dinner and slow trip back to the schooner during golden hour. Fantastic!”


    Fred Wyckoff and Gerri Haan
  • “Steering a 157 foot schooner under full canvas in 20-25 plus winds was exciting, with the wind tearing at my hair. With beautiful blue skies and turquoise seas in 80 degrees, what could be better?”


    Marge Benning, Denver CO