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.

Embrace the adventure of a lifetime and journey from the British Virgin Islands to Bermuda on the majestic Arabella. Don’t miss this unparalleled blend of adventure and luxury at sea.

Embrace the adventure of a lifetime and journey from the British Virgin Islands to Bermuda on the majestic Arabella. Don’t miss this unparalleled blend of adventure and luxury at sea.

Belize’s sailing experience extends beyond the sea, offering captivating inland ventures. With BSV’s fully crewed catamarans, guests enjoy the ultimate all-inclusive charter, accessing the world’s largest living barrier reef and remote sites.

Explore Belize’s paradise islands on your own private luxury catamaran. Learn sailing from ASA certified instructors & crew. Snorkel, kayak, and fish in crystal clear waters. Enjoy gourmet meals & exotic drinks prepared by your crew. Experience a different destination every day on this ultimate sailing vacation!

Join Horizon Sailing School for a women-only learn-to-sail vacation in the beautiful British Virgin Islands. During this week-long liveaboard experience, you’ll build confidence on the water while sailing between iconic islands like Norman Island, Virgin Gorda, and Jost Van Dyke. Aboard a comfortable 34–44 ft monohull, you’ll learn sailing fundamentals, coastal cruising, and bareboat skills while earning ASA 101, 103, and 104 certifications. With small groups, expert instruction, and time to snorkel, explore beaches, and enjoy island life, this trip combines sailing education with a relaxed Caribbean adventure.

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 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.

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!

Learn to sail while exploring the beautiful British Virgin Islands on this week-long liveaboard adventure with Horizon Sailing School. Aboard a comfortable 34–44 ft monohull, you’ll build sailing skills while visiting iconic destinations like Norman Island, Virgin Gorda, and Jost Van Dyke. During the trip you can earn ASA 101, 103, and 104 certifications, gaining the knowledge and confidence needed to bareboat a monohull. With small groups, expert instruction, and time to snorkel, explore beaches, and enjoy island life, this experience blends hands-on sailing training with a relaxing Caribbean vacation.

Join American Sailing Vacations and Cruise Abaco for a week of clear, warm waters, white-sand beaches, and unforgettable sailing through the Abacos. This flotilla offers the perfect mix of freedom and fun — explore the Out Islands by day and share sundowners with new friends each evening.

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 can be on board, guiding you through ASA 103, 104, and 114 certifications as you explore one of the world’s best sailing destinations. Don’t need certifications? Charter captains are available by request.

Learn to sail while exploring the beautiful British Virgin Islands aboard a 40–44 ft catamaran. During this week-long liveaboard adventure with Horizon Sailing School, you’ll gain hands-on sailing experience while visiting iconic islands like Norman Island, Virgin Gorda, and Jost Van Dyke. The course includes ASA 103, 104, and 114 certifications, onboard accommodations, instruction, and most meals.