Caribbean

To pay tribute to our founder Lenny Shabes we are calling all sailors to join us for a week of sailing in the beautiful BVI’s to enjoy festivities ranging from sundowners to regattas.

The BVIs are the perfect destination for your first charter experience. A flotilla gives you the support group that makes that first charter experience even easier. And the weather in late February in the BVIs is some of the best.

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.

Embark on the ultimate sailing adventure with our comprehensive 9-day ASA Liveaboard Monohull Class. This immersive course is designed for aspiring sailors seeking to master the essentials of sailing, with hands-on training and real-world experience. Over the span of a week, you will cover ASA 101, 103, and 104 certifications, ensuring you are well-prepared to handle various sailing conditions and navigate with confidence!

Join Wet & Salty Adventure Sailing School in Barbados for a 6-day intensive liveaboard course combining ASA 103 (Coastal Cruising) and ASA 104 (Bareboat Cruising) to help sailors refine their skills and gain confidence as a skipper. With steady trade winds, deep blue waters, and hands-on training in navigation, anchoring, and passage planning, this Caribbean adventure prepares you for independent cruising and chartering worldwide.

Set sail in one of the world’s premier cruising grounds—the U.S. Virgin Islands. This immersive, week-long sailing course combines world-class instruction with an unforgettable vacation. With small class sizes and award-winning ASA-certified instructors, you’ll earn your bareboat charter certifications while exploring crystal-clear waters, stunning beaches, and vibrant island culture aboard a luxury catamaran.

Set sail on a 7-day learn-to-sail vacation in the stunning British Virgin Islands with Go Sail Virgin Islands. Earn ASA 103, 104, 114, and the International Proficiency Certificate (IPC) while exploring top island destinations aboard a luxury catamaran. With award-winning instructors, small class sizes, and hands-on training, this unforgettable sailing experience combines world-class education with adventure, relaxation, and island-hopping fun.

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!

Join the Ultimate Sailing Experience! Set sail with us in the stunning British Virgin Islands, whether you want your own boat or prefer to share with others. Certified ASA instructors will be on board, guiding you through ASA 103, 104, and 114 certifications (for an additional fee) as you explore one of the world’s best sailing destinations. $3500 per person (double occupancy cabin with private head and shower).

Join the Ultimate Sailing Experience! Set sail with us in the stunning British Virgin Islands, whether you want your own boat or prefer to share with others. Certified ASA instructors will be on board, guiding you through ASA 103, 104, and 114 certifications (for an additional fee) as you explore one of the world’s best sailing destinations. $3500 per person (double occupancy cabin with private head and shower).

Experience the vibrant spirit of the Caribbean — from the historic harbors of Antigua and the pink sands of Barbuda to the glamorous shores of St. Barths. Sail through turquoise waters aboard the luxurious schooner RHEA, as we follow the exhilarating spectacle of the St. Barths Bucket Regatta. Bask in the steady trade winds, savor world-class hospitality, and witness the unmatched beauty of classic yacht racing in one of the world’s most breathtaking destinations.

Join American Sailing for an unforgettable 8-day adventure racing in the Antigua Classic Yacht Regatta aboard the luxury sailing yacht Chronos. Compete, cruise, and celebrate in the Caribbean’s most iconic regatta while enjoying world-class service, stunning beaches, and vibrant island culture.