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!
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!
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.
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.
Embark on an enchanting 8-day, 7-night sailing voyage through the stunning Saronic Gulf and its neighboring regions in Greece. This trip provides a blend of historical exploration with leisurely island-hopping, offering a captivating experience for sailing enthusiasts and newcomers alike.
Sailing in the Grenadines allows you to experience a variety of landscapes and activities. You can anchor in a quiet cove for a day of swimming and snorkeling, visit lively markets and historic sites onshore, or enjoy a sunset from the deck of Chronos. The Tobago Cays, a protected marine park, is a highlight, offering some of the best snorkeling and diving in the Caribbean.
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.
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.
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.
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.
“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.”
“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!”
“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!”
“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?”