A Learn to Sail Vacation is a sailing adventure where you gain hands-on sailing experience while exploring destinations around the world. Guided by professional ASA instructors, you’ll learn essential sailing skills during the day and unwind in stunning coastal locations by night. You can expect a mix of structured lessons and real-world practice, including hoisting sails, navigation, and docking, all while sailing to beautiful islands, snorkeling in crystal-clear waters, and enjoying spectacular sunsets. Whether you're a beginner or looking to advance your skills, this vacation blends education, adventure, and relaxation into the ultimate getaway.
This immersive course covers ASA 101, 103, and 104 certifications over nine days, providing participants with a solid foundation in sailing while exploring the stunning waters of Barbados.
Embark on a week-long journey aboard the training vessel Starlight, guided by experienced American Sailing-certified instructors. This program offers hands-on sailing skills amidst the breathtaking beauty of Corfu and Paxos islands.
See the complete list of Learn to Sail Vacations at American Sailing Vacations Learn to Sail Vacations
A flotilla sailing vacation is a unique and social adventure where multiple sailboats travel together, following a planned route. Each boat is either captained by experienced sailors or led by a professional skipper, while a lead boat guides the entire fleet, providing support, navigation, and local expertise.
What You Can Expect on a Flotilla Sailing Vacation:
A Perfect Balance of Freedom & Support – Enjoy the thrill of captaining your own boat while having the reassurance of an expert-guided itinerary.
A Social & Fun Atmosphere – Meet like-minded adventurers, share experiences, and join in on group activities like beach BBQs, sunset cocktails, and island excursions.
Relaxation & Adventure in One – Whether you're seeking excitement on the water or peaceful moments at sea, a flotilla offers the perfect mix of both.
Hassle-Free Travel – The lead crew handles logistics, weather updates, and any challenges along the way, ensuring a smooth and enjoyable journey.
A flotilla sailing vacation is ideal for couples, families, or groups of friends looking for an unforgettable, community-driven sailing experience. Whether you’re a beginner or an experienced sailor, it’s a stress-free way to explore the world by boat!
Explore stunning islands, secure anchorages, and charming harbor towns while enjoying the safety and camaraderie of flotilla-style sailing. With expert guidance and countless learning opportunities, you’ll have the chance to enhance your skills and knowledge. Join us for a Pure Michigan adventure like never before!
Set for August 2025, this adventure explores the stunning Bay of Kotor, charming coastal towns, and rich cultural experiences, all while sailing in the supportive environment of a flotilla
See the complete list of Flotillas at American Sailing Vacations Flotillas
This 8-day journey aboard a 30-meter luxury sailing yacht visits destinations like Split, Hvar, and Korcula, offering a once-in-a-lifetime sailing vacation along the Dalmatian coast.
Departing from Newport, Rhode Island, this cruise visits Martha’s Vineyard, Nantucket, and Cuttyhunk, providing a rich blend of sailing and cultural experiences in New England’s iconic locales.
See the complete list of Luxury Cruises at American Sailing Vacations
