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14-21 June 2026
Explore the stunning British Virgin Islands with us on a unique and adventurous flotilla journey! This flotilla offers an incredible opportunity to discover the BVI’s hidden gems and off-the-beaten-path destinations that most charters miss. We’ll sail to picturesque anchorages, vibrant snorkeling spots, and charming islands, creating an unforgettable experience away from the more crowded locations. Our itinerary promises a rich variety of less-visited bays and coves that capture the true essence of the BVI.
An example itinerary highlighting possible activities, overnight stops, and routes. (Not for navigation.)
Join us for an unforgettable sailing adventure from Sunday, June 14th (6 pm) to Sunday, June 21st (11 am), 2026. Our first night will be spent in the marina, and we’ll set sail on Monday morning.
Everyone is welcome—whether you’re a seasoned sailor or a complete beginner. Come solo, with a partner, or bring friends and family!
Our flotilla will be led by Calypso Sailing Life team members, including:
Capt. Mark Noneman: USCG Master, American National Standards Instructional Skipper, and Flotilla Co-Leader.
Capt. Sharon Noneman: USCG Captain and Flotilla Co-Leader.
We have a selection of Sunsail and Moorings monohulls and catamarans available for this flotilla. To join, you must book through NauticEd Sailing Vacations, ensuring you get the same great price as booking directly. We offer two options:
By the Cabin Charter: Sail with an experienced Instructional Skipper. Perfect for those who want to learn as they explore, or for those who prefer not to captain their own vessel.
For our “By the Cabin” luxury charter option, enjoy a hassle-free sailing experience with an instructional captain, hostess, provisioning (breakfast, lunch, snacks, and three dinners onboard), beverages, mooring fees, refueling, BVI cruising fees, and a stand-up paddleboard—all included. Sail aboard the lead boat, a luxurious Moorings 5000 catamaran with Captains Mark & Sharon Noneman for $7,900 per cabin (double occupancy).
Private Boat Charter: Rent an entire boat and fill it with friends and family!
Costs depend on the size and amenities of the boat. Additional expenses include flights, provisioning, mooring fees, water toys, refueling at the end of the charter, and a cruising tax (around $30 per person for the week). A $250 per cabin flotilla fee is also applicable. Let us know your preferences and we’d be glad to send you suitable options.
Choose from:
Bareboat Charter: You skipper the boat yourself
Optional Skipper: We will hire a skipper for you
Optional NauticEd Instructional Skipper: Enhance your sailing skills with a professional instructor onboard
Private Boat Charter Costs:
Monohulls: Start at approximately $9,000 for a 41-foot (3-cabin, 6-pax) boat (1-3 years old).
Catamarans: Start at approximately $16,000 for a 45-foot (4-cabin, 8-pax) boat.
Skippered Option: Add $1,820 for the cost of the skipper.
NauticEd Instructional Skipper Option: Please ask us for the cost of an Instructional Skipper.
If you’re looking to gain some experiential training, then this is a great opportunity to hang with the best of the best NauticEd trainers. We say “light instruction” because – this is a vacation but with that comes gaining the experience of what a sailing vacation offers and some how-to’s when operating a boat on such a vacation.
Those who are competent skippers bringing their crew for family and friends are welcome and encouraged to join the fun. Or, those that want to just hang back and get captained around with their feet up in the hammock – we have a place and a captain for you as well.
The 2026 British Virgin Islands Sailing Flotilla is a casual flotilla without a ‘theme.’ This is NOT an adult-only flotilla, a party yacht week, or a flotilla focusing solely on hiking or wines or yoga. We’re laid back and run our flotillas that way. Of course, you’re welcome to explore as you see fit. There is a no ducks-in-a-row mentality; a flotilla offers you independence with peace of mind as well as fun and camaraderie with other flotilla sailors.
Learn more about what is a sailing vacation and a sailing flotilla
Easy to get to (fly into St Thomas and ferry to BVI (Tortola) or fly into BVI’s Beef Island)
Sailing Capital of the World
Pirate history
Mix of relaxation and adventure
Snorkeling, hiking, and nature abound
Short sails with consistent trade-winds and line of sight navigation
Stunning beaches
Delicious Caribbean food and drinks
Photographs of your adventure that will last a lifetime
Great sailing for both new sailors and experienced skippers
Check out our BVI charter recap
Can’t make the flotilla, but want to sail the BVI—let the agents at NauticEd plan your perfect BVI sailing vacation. We know the area, we know the good companies (and the not so good). We don’t charge you a fee and you get our expertise.
Inquire about a vacation in the BVI
Want to go somewhere else?
We are location experts. Chances are … we’ve been there! Mediterranean, Pacific, Caribbean, Asia, ‘Stralia Mate’, Indian Ocean, and many more!
Inquire about a different sailing vacation
Other Flotilla Opportunities?
What is Experiential Learning or an Instructional Skipper?