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Sailing in Tortola
The largest of the British Virgin Islands and the charter hub of the Caribbean, with the Sir Francis Drake Channel running flat water down its southern side.
Why here
Tortola has the deepest bench of American Sailing Association schools in the Caribbean, and the geography is the reason people learn here rather than somewhere prettier. The Sir Francis Drake Channel is flat, the islands are within sight of each other, and the anchorages are close enough that a student can make a passage, navigate, and anchor for the night all in an afternoon. Three schools run liveaboard courses from the marinas around Road Town, including the full ASA ladder up to catamaran and instructor level. It is the classic place to convert a certificate into an actual bareboat charter.
Best months
Tortola sits at 18 degrees north, inside the Caribbean insurance hurricane box, which runs through November 30 inclusive. December is therefore the first clean month of the season and conditions improve from there through the winter trades. Note that no local operator publishes a November restriction, so this is an insurance and risk judgment rather than something the schools will tell you. Winter trades blow steadily from the east at 15 to 20 knots, which is close to ideal teaching wind. Christmas and New Year are the busiest fortnight of the year on the island.
Getting there & around
Fly into Terrance B. Lettsome International on Beef Island, connecting through San Juan or St Thomas, or take the ferry from St Thomas. The three schools are spread across different marinas rather than all at Nanny Cay: Village Cay and Penn's Landing also host operations, so confirm your base before arranging transfers. Courses are mostly liveaboard, so accommodation is the boat. Book December well ahead, since the holidays fill the charter fleet. One correction worth carrying: the Round Tortola Race is a spring event despite some tourism listings still advertising a November date.
Skill levels: beginner, intermediate, advanced
Schools & guides (3)
Horizon Sailing School
SchoolASA school at Nanny Cay Marina teaching the full 101 to 118 student ladder plus 201 to 218 instructor training, with catamaran options on several courses.
Rob Swain Sailing School
SchoolASA school running 101 through 118 on a fleet of 36 to 54 foot boats, with liveaboard courses and charters through the Sir Francis Drake Channel.
Top Tier Sailing School
SchoolASA school running liveaboard fast-track programs covering 101, 103, 104 and 114 plus a bareboat charter starter course.
Also good for sailing in December:
Torn between Tortola and Tobago Cays for December?
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