Your future doesn’t start someday. It starts today. Set sail on the vacation you’ve been dreaming about? We believe you’re ready.

"Your journey begins where the dock ends."

Your adventure begins here.

Set sail with American Sailing aboard world-class yachts in some of the most breathtaking destinations on earth — from the rugged coastlines of New England to the turquoise waters of the British Virgin Islands, and from the ancient shores of Greece to the vibrant beauty of Croatia.

This isn’t just a vacation — it’s your chance to chase the horizon, feel the wind in your sails, and discover who you are out on the open water. Whether you’re making lifelong friends on a flotilla, learning to sail in paradise, or unwinding on a luxury cruise, one thing is certain:

The time is now. Don’t let another year pass without answering the call of the sea.

 

Upcoming Cruises & Flotillas

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DISCOVER LA PAZ A GUIDED FLOTILLA

Go Baja Sailing
Availability : April 2025

Sailing the waters around La Paz, Mexico, is a truly magical experience. Nestled in the Sea of Cortez, often referred to as the “Aquarium of the World,” La Paz offers crystal-clear turquoise waters, calm seas, and stunning, unspoiled islands just offshore. With no Pacific ground swell, the waters are as smooth as a lake, making for relaxed and enjoyable sailing conditions.

From$1,998
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2025

British Virgin Islands Flotilla ~ Lenny Shabes Sailing Festival

American Sailing
Availability : June 15-21, 2025

Enjoy seven days and six nights of sailing alongside fellow boats for one epic flotilla experience. Explore the iconic baths, get in on a small boat regatta at the famous Bitter End Yacht Club, and swim to shore to visit the iconic Soggy Dollar Bar. It’s going to be an action-packed sailing adventure!

From$2,499
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LIMITED CABINS AVAILABLE

EXPLORE CROATIA ABOARD CATALEYA A LUXURY CRUISE

American Sailing
Availability : July/September 2025

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.

From$3,000
(1 Review)
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LIMITED CABINS AVAILABLE

EXPLORE THE AMALFI COAST ABOARD CHRONOS A LUXURY CRUISE

American Sailing
Availability : July 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.

From$4,050
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NEW

Grand Tour of New England Aboard Arabella A LUXURY CRUISE

American Sailing
Availability : July/August 2025

Imagine this: You’re on the deck of a magnificent 157-foot yacht, the Arabella, cruising the crystal-clear waters of New England. The wind whispers through the sails, the sun warms your skin, and the breathtaking coastline unfolds before you.
This isn’t a dream; it’s your reality with the American Sailing’s Grand Tour of New England aboard Arabella.

From$2,400
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NEW

Sailing The South of France aboard Chronos A LUXURY CRUISE

American Sailing
Availability : October 2025

Embark on a luxurious sailing trip starting in St. Tropez, exploring Cap Bregancon and the stunning Îles d’Hyères, including Île de Porquerolles. After relaxing on beautiful beaches, return to St. Tropez to discover iconic sites like Place des Lices and the citadel. Experience the best of the French Riviera.

From$4,050
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SOLD OUT

ST TROPEZ & MALLORCA ABOARD CHRONOS A LUXURY CRUISE

American Sailing
Availability : October 2025

Your journey begins in the glamorous port of St. Tropez, known for its luxury yachts, vibrant nightlife, and charming old town. As you set sail from this iconic French Riviera destination, the Mediterranean’s turquoise waters will guide you toward Marseille. Along the way, you can enjoy the stunning coastal landscapes, with opportunities for swimming in secluded coves or relaxing on deck.

From$4,050
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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. 

Testimonials

  • “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