Your time is now.
Imagine yourself sailing in the British Virgin Islands, spending a week exploring the islands you’ve dreamed about. Feel the sunshine on your face, the warm Caribbean water surrounding you, and the soft sand under your toes. Swim ashore to the famous Soggy Dollar Bar on Jost Van Dyke, experience the thrill of endless jumps off the legendary Willy T and sail a sleek catamaran with perfect wind alongside a small group of like-minded adventurers. This is your time to meet new friends, and to fully reset in paradise.
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!
Escape to a sailing paradise with our British Virgin Islands flotilla, a sailing adventure where you can relax or learn as you go, surrounded by friendly, experienced sailors. We take care of all the logistics—from captaining the boat to provisioning—so all you need is your suitcase and sunscreen. New for 2026, experience the unforgettable Ultimate Dock Party, sail on a luxurious 6-cabin mega catamaran, enjoy a boat raft-up at sunset, and channel your inner sailor in a multi-day regatta through stunning Caribbean waters.
No experience is necessary, all you need is a reason to have a good time in the British Virgin Islands.
A flotilla is a group of boats sailing together from destination to destination, sharing the joy of being on the water and the excitement of what’s ashore. In this flotilla, we anticipate 10-20 boats made up of sailors and non-sailors from around the world coming together for one amazing week. Book your cabin with American Sailing, and you’ll have your own skipper, a luxury catamaran, and a dream sailing vacation waiting for you.
This is the third year of the Annual Lenny Shabes Sailing Festival and we have a few new things to add in 2026.
The Ultimate Dock Party: Start your journey with a bang! On the first night, get ready for an unforgettable dock party. Meet your crew, dance the night away, and get acquainted with your vessel.
Sail Aboard a Mega Catamaran: For the first time, we’re introducing a 6-cabin mega catamaran! Experience luxury, comfort, and world-class sailing with plenty of space for your friends or family.
The Boat Raft-Up: Join the iconic raft-up, a highlight of last year’s festival where we gather for camaraderie, fun, and breathtaking sunsets. Don’t forget those slushie drinks from the rum-runner! This year, we may even have some live entertainment!
Multi-Day Regatta: Channel your competitive spirit in the multi-day regatta, racing through some of the most scenic waters in the world. Whether an experienced sailor or a beginner, this regatta is for everyone!
The British Virgin Islands are a picturesque Caribbean destination known for their pristine beaches, crystal-clear waters, and stunning natural scenery. With over 60 islands and cays to explore, there are plenty of options for visitors looking to soak up the sun, relax on the beach, and enjoy the island’s laid-back atmosphere. The British Virgin Islands’ consistent trade winds and calm seas provide perfect sailing conditions for both beginners and seasoned sailors. Island-hopping is a breeze, allowing travelers to immerse themselves in various cultures, cuisines, and activities. Water sports abound, from snorkeling and diving to paddleboarding, ensuring there’s always something exciting to do. Whether you seek adventure, relaxation, or you aim to expand on your sailing education, sailing through the British Virgin Islands offers an irresistible destination for anyone looking to experience the Caribbean’s finest treasures.
You’ll be cruising aboard a luxury sailing catamaran, 42ft or larger. All the yachts have spacious, queen-sized cabins with their own head/shower, air conditioning throughout, and a generator. While you’ll be spending most of your time outside, the interiors are both spacious and stylish. The yachts have fully equipped galleys and comfortable saloon areas. Cockpit areas are well-ventilated and sheltered, the perfect spot to socialize with new friends! You’ll find various seating areas around the yacht, in the cockpit, on the bow, the coach roof, and on the flybridge, all perfect for sunbathing, lounging, and enjoying a drink or three! Sail controls are located by the helm station, making these yachts great to get everyone involved in the activity.
*Itineraries are subject to change due to weather or other circumstances beyond our control.
