We provide the best cruises and flotilla trips.

Book your trip today with ease

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. 



American Sailing
Availability : Jul 19, 2025

Experience the enchanting allure of the Italian coast – from the picturesque Amalfi and Positano to the captivating islands of Capri and Ischia. Bask in the sun-drenched hillside villages, where the air is imbued with the tantalizing scent of citrus. Indulge in the delights of limoncello and embrace the charm of “Molto Bene.” Embark on a journey of luxury aboard a sailboat, as we navigate the azure waters of the Amalfi Coast in the summer of 2025.

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American Sailing
Availability : Dec 2024 | Jan 2025 | Feb 2025

Embark on a transformative journey through the British Virgin Islands aboard Arabella with American Sailing. From the lively shores of Jost Van Dyke to the serene beauty of Virgin Gorda, every moment is promised to be infused with laughter, camaraderie, and pure joy. Lose yourself in the rhythm of island life, where each day brings new adventures and lifelong friendships. Your dream itinerary awaits – let Arabella be your guide through paradise.

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American Sailing
Availability : Oct 21, 2024

Embark on a 6-day luxury sailing adventure aboard Chronos Yacht, exploring Mallorca to Menorca with American Sailing. Enjoy personalized service, secluded coves, and stunning coastlines with a small, passionate group. This intimate voyage offers full-board luxury, breathtaking views, and unique experiences in the heart of the Balearic Islands. Set sail for an unforgettable journey this fall.

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American Sailing
Availability : Sep 14, 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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Grand Tour of New England Aboard Arabella A LUXURY CRUISE

American Sailing
Availability : August 2024

From the moment you board Arabella in Newport, Rhode Island, the tone is set for a sailing adventure. Your week aboard Arabella will be filled with full sails on the way to Martha’s Vineyard, Nantucket, and Cuttyhunk. This is more than a sailing vacation; it’s an adventure for the soul.

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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