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A Tale of Two Boats and the Anguilla Connection

Photography by Geoffrey Brooks, Curator – Virgin Islands Maritime Museum

Towards the end of the 1930’s Virgin Island shipwrights began to build larger sloops which broke away from the unique design that had been used for over 150 years. These sloops had bow sprits, they were cutter rigged (that is they carried two or more jibs in front of the mast) and they were gaff rigged on the mainsail. One of the earliest was the Yolanda built by Leopold Smith in Road Town.

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As the economy began to change in the 1950’s, bigger cargo boats were needed to carry construction materials for the growth in new housing, hence the need for larger sloops. In 1952, Osmond Davies built the 40ft Bells of St Mary in East End. Later came the Parham Town by Edward Frett at 45ft and finally, the sloop we are concerned with, the Amanda Stoutt built in 1956 by Claremon Floyd Davies. She was 42ft in length.

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Amanda Stoutt was built for Captain Warren Stoutt of Little Apple Bay – she was a fine boat and very fast; however, one problem these larger sloops faced was that they were difficult to control. The length of the boom and the large size of the mainsail made them hard to handle. Someone once told me that a single person could not hold the tiller on Amanda Stoutt and that many times they would have to tie a line on the tiller just to maintain course.

The answer to this problem was to transcend from sloops to schooners. Schooners—with the sail area spread over two masts—were much easier to control and allowed for even larger vessels with more cargo capacity. Schooner building was however the domain of Anguilla. Anguillans excelled at building schooners and for very good reason. Anguilla had salt. Trading schooners from Nova Scotia would stop and load salt in Anguilla to carry back home in order to preserve fish which would then be returned to the Caribbean to trade for molasses. This is where our traditional food ‘salt fish’ came from.


During the great depression in the 1920’s, Caribbean people migrated to the Dominican Republic and Cuba to find work in the Sugar cane fields. The Anguillans provided transport with schooners they learned to build from the Nova Scotia sailors they had been trading with for years.

Boat building became one of the mainstays of the economy of both the Virgin Islands and Anguilla – the Virgin Islands specialising in a unique design of sloop and Anguilla in large sea worthy schooners.

People came from all over the region to purchase these boats. The similarities between our two territories does not end there. The very first settlers of Virgin Gorda came from Anguilla and had names like Hodge, Vanterpool and Romney just to name a few. The capital of Anguilla is The Valley and the connections go on.

It made perfect sense that when Captain Rudolph Hodge of Cane Garden Bay decided to build a schooner, he would bring in a shipwright from Anguilla to do the work. In 1957, Anguillan shipwright McDuff Richardson relocated to Cane Garden Bay and began construction of one of the Virgin Islands’ most beautiful and well-loved vessels the Pride of Tortola or just the Pride as she was called. The Pride was 63ft in length and clearly a thing of beauty, fitted with a Perkins Diesel engine making her an auxiliary schooner. I have always considered both the Pride and the Amanda Stoutt two of my favourite local boats. I built models of both vessels and they are on display at the Maritime Museum at the H. Lavity Stoutt Community College.




The story of these two lovely vessels takes an interesting turn when in 1963, Captain Rudolph Hodge decided to sell the Pride to Capt. Warren Stoutt and along with cash, the Amanda Stoutt was traded.

Captain Stoutt kept the name Pride of Tortola for the schooner, but Capt. Hodge changed the Amanda Stoutt to the Pride of Tortola II.

The story told is that the deal had been made, but no money or boats had changed hands when a big cargo became available. Capt. Hodge asked Capt. Stoutt if he could do this last job before they exchanged boats, but Capt. Stoutt insisted that the sale go through first. Capt. Stoutt then got the cargo and his profit paid for the purchase of the boat.

Both vessels continued to ply their way through the region trading and carrying cargos and people to various destinations. Two years after acquiring the Pride she was lost on Omen Rock off Magens Bay in St. Thomas. She hit at 6am on November 22, 1965 with a full load of lumber.

The weight of her cargo split the hull wide open and she sank in fifteen minutes. Thankfully, Capt. Stoutt and his crew made it to shore safely.

Capt. Stoutt went straight to Anguilla and purchased a veteran schooner called the Baby Mack built by Anguillan shipwright Mack Conner. The Amanda Stoutt continued to sail as the Pride of Tortola II for seven more years until she too sadly sank 20 miles South of St. Thomas on July 8, 1972. We have no information at present as to why or if there was loss of life.

As these schooners and large sloops faded out, they were replaced first by wooden motor vessels and then by the steel barges that we know today. At present, you can go to Port Purcell and find large steel cargo vessels lined up at the dock – if you look closely, you will see names like Tortola’s Pride and Warren’s Pride, so it would appear that the legacy lives on.

Geoff Brooks, Curator - Virgin Islands Maritime Museum

Geoff Brooks, Curator - Virgin Islands Maritime Museum

Geoffrey is the curator of the Virgin Islands Maritime Museum. He pioneers and takes part in many of the initiatives related to the traditional art of sloop building.
Geoff Brooks, Curator - Virgin Islands Maritime Museum

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