For over a hundred years, the Tortola Sloop was the jack of all trades in transporting people and goods among the Virgin Islands. A combination of pick-up truck and automobile, this nimble one-masted sailboat plied among the islands, graceful and yet immensely practical.  

The design of the Tortola Sloop is unique to the Virgin Islands and appears to have originated in West Africa. Take just a glance at one of today’s fishing boats pulled up ashore on the Cape Verde Islands and you’ll recognize the full hull, the flat stern with its rudder, and the wooden construction. The first of these boats to sail in the Virgin Islands were likely constructed  by master boatbuilders who had arrived as slaves.

These single-masted boats have main sail, and a jib. Their hulls are fashioned from white cedar, local to the Virgin Islands. They measure about twenty feet in length and feature a wide beam so they can  carry plenty of cargo. Their stability is increased by placing heavy stones in the bottom of the hull to counteract the tipping (heeling) force of the wind.

Tortola Sloops were still numerous through the 1970s and were amazingly versitile. I once saw one being loaded out with a VW Beatle at the pier of Charlotte Amalie, St. Thomas. Also, I’ve seen them sailing serenely on the Caribbean, full of passengers, and having very little distance (“freeboard”) between the deck and the water. 

These days, motor vessels with aluminum or fiberglass hulls have taken over the jobs of cargo and passenger transportation among the islands, and a few years ago, only a handful of Tortola Sloops remained. Happily, the art of their construction and sailing has been retained, and new boats are arriving each year. They are built in simple, open-air boatyards  and sailed mainly for fun, such as in the VP Bank Tortola Sloop Spring Challenge.