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Bareboats BVI - Bareboat Sailing and Motor Yacht Charters

Is Vigilant the Oldest Sailing Sloop in The Western Hemisphere?

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Moon Beam & Youth Instructor

Vigilant was built by Willie Penn in East End, Tortola. Some say she was built in 1880 and others claim 1882. In either case, Vigilant is the oldest known wooden sailboat in the Caribbean!

Known as a "Tola Boat", identifiable by her distinctive, "leg of mutton" mainsail, Vigilant has passed through several hands in her 100 plus year history! She was owned by builder, Willie Penn for some time until he sold her to Bim Thomas who sold her to Isiah Stoutt ... all of Tortola.

In 1920, Vigilant found a more permanent home in Hannah's Bay, with the MacTavious family of Tortola. She was employed as an inter-island work boat in return for her care and maintenance. By 1994, her usefulness as a work boat had long since passed and she was purchased from Randolf MacTavious by the BVI Government for the H. Lavity Stoutt Community College, Marine Studies Department.

Jeff Brooks, is charged with the care and maintenance of the three remaining Tortola Sloops (including Vigilant) and he believes she may even be the oldest wooden sailboat of her type in the Western Hemisphere and possibly the world! Jeff is always on the hunt for a boat which might prove older ... but to date, has not found one.

For several hundred years, these stalwart work horses of the Caribbean were used as inter-island passenger vessels and cargo boats. Incredibly, the Tola Boats were often used to carry livestock to neighbouring islands, including cattle, pigs, sheep and goats. I'd hate to imagine what it might have been like having an 800 or 900 pound, seasick bull aboard one of these tiny vessels!

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Vigilant in happier days
Photo courtesy of Nancy Terrell
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Sweethearts of the Caribbean Race
Photo courtesy of Nancy Terrell

Until Vigilant popped a plank during a race and sank, she had always been a contender in the "Sweethearts of the Caribbean", wooden boat regatta! With stained sails and rust streaks on her white painted hull, this was to be the last time Vigilant would sail the waters of the BVI.

Another treasure of the Caribbean is the marvelous Carib Canoe, Gli Gli, seen in the foreground of the photo above.

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Dry rot consumed her
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Popped Planks

Since she sank, this valiant little Tola Boat sat on the hard at Virgin Islands Shipwrights in Soper's Hole, Tortola for several years, waiting for a well deserved overhaul that was not to be.

This once strong and beautiful little sailing vessel that bravely tackled the Caribbean Sea for so many years, has been hauled for the last time.

Vigilant on the hard
Vigilant - circa 2004

Photos of the Tortola Sloop Shootout - BVI Photos

All photos of Vigilant and the Tortola Sloops are copyrighted by Bareboats BVI or Nancy Terrell and may not be used on the internet without prior written consent.


For more information about sailing the British Virgin Islands,
contact our Tortola bareboat charter specialist!

Phone: (284) 495-4168 Tortola, British Virgin Islands
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Text & Photos Copyright © Bareboats BVI. All rights reserved.
Launched: August 16, 2004 - Last Updated: January 27, 2014