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.

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 Caribbean Sail Training in Antigua for an unforgettable offshore sailing adventure aboard the legendary S/Y Spirit of Juno. This hands-on expedition combines real-world seamanship, offshore passagemaking, and exploration of some of the Caribbean’s most remote and beautiful islands. Designed for sailors looking to build confidence on larger yachts, you’ll gain practical offshore experience while discovering a side of the Caribbean few ever see.

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.

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.

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.

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!

Explore the stunning British Virgin Islands on a hands-on sailing adventure through crystal-clear waters, secluded anchorages, and vibrant island communities. Earn your ASA 104 Bareboat Cruising or ASA 114 Cruising Catamaran certification while gaining real-world experience aboard a 48-foot monohull or 46–48-foot catamaran. With steady trade winds and short passages between islands, the BVIs provide the perfect setting to build confidence and create unforgettable memories on the water.

Escape to the crystal-clear waters of the British Virgin Islands on an unforgettable 7-night catamaran sailing adventure. Sail aboard a luxurious 40–44 ft catamaran, explore iconic destinations like Anegada, Jost Van Dyke, and Norman Island, and enjoy the perfect balance of relaxation, island exploration, and hands-on sailing. Whether you’re looking to earn ASA certifications or simply experience one of the world’s premier cruising grounds, this all-inclusive sailing vacation offers the adventure of a lifetime.