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The Origins of Sloop Racing and the Fastest Boat  


If you ever are in the company of two or more BVI senior citizens and the topic of conversation is traditional wooden sloops, the subject of which was the fastest vessel will invariably emerge. So which boat was the fastest?

The answer depends on who you are talking with and where they are from. People are very passionate about this subject and very loyal to their home village. Folks from the North Shore will say the Dixie or the Consolation. In East End and Parham Town, it could be the Pilgrim, the Cedar Branch or the Lady D. In Sea Cow’s Bay, the Florena or the Olive, known as the flag boat. In West End, it would be the Flame.

For well over 100 years, the Virgin Islands were the primary supplier of beef to St Thomas. Along with Beef, we carried other livestock, ground provisions, and charcoal. They exchanged these products in Charlotte Amalie for the supplies they needed to live.

Once a week was Shipping Day in Road Town – sloops would load up at the Jetty in Road Harbour and sail to West End where they would meet other Sloops from the North Shore and Anegada. They would ‘clear out’ (clear customs) and sail together for Charlotte Amalie. Whoever reached first would have the advantage of selling their products ahead of the others. The competition was fierce and a fast boat was definitely an asset.


Once business was concluded, it was another challenge to see who could sail back to West End and ‘Clear In’ before the others and then sail on to their home village. The route they took was identical to that used by our ferry boats today and the section between West End and Red Hook in St Thomas was known as ‘The Ghut.’ This is how sloop racing began and it eventually found its way into our annual Festival celebrations as a popular event held on August Tuesday.

Now in this story, I would like to deal with a sloop called the Lady D and a race against the Consolation and the Dixie, which took place in the 1940’s. The Lady D was built in East End (Red Bay to be exact) by expert Shipwright Haldane Davies.  I had the privilege of interviewing Mr. Davies before he passed away and one of the many things he shared with me was the story of this sloop.

Haldane said that the Lady D was the fastest boat ever built in the Virgin Islands. Of course he built her so his opinion might be a little biased. She was however, a very, very swift boat.

Haldane said that Father God had guided his hands when he built her and that her lines below the waterline were different from any other boat that he built.

“She would get up and fly,” he said and she could out reach and out point any sloop in her day. It wasn’t long before word of this fast East End sloop began to spread to the other communities. One day in the 1940’s, the Lady D was clearing out of West End with the other sloops bound for Charlotte Amalie. As she cleared customs, she met two Cane Garden Bay boats, which had purposely waited for her. They were the Dixie, Louis Callwood’s boat and the Consolation belonging to Sonny Henly and made famous in the ballad of Ella Gift with the rum hidden in her pantalets.


The race began but as they passed Great Thatch and headed into the Ghut, the wind became light and it favoured the other boats.

Haldane was on board the Lady D and at the helm was his cousin Adolphus Penn.  As the Dixie and the Consolation forged ahead, in the light airs Haldane settled in for a nap. When he awoke, the wind had increased and they were at the other end of the Ghut. He looked ahead to see how far the two boats had gotten, but could see nothing. He asked Adolphus where they were and was told to look behind them.

Far in the distance were the other boats and as they reached the rocks known as the Cow and the Calf, they made their turn to head towards Charlotte Amalie. The race didn’t end here, for when it was time to go back, Sonny Henly and Louis Callwood said that the real test is going into the wind and that would determine whose sloop was fastest.


This time they were joined by a St John boat and all four left together. Lady D was in her element and she could out point any other sloop when heading into the wind. She got below the other boats and never looked back. Haldane said that they reached West End, cleared Customs and were on their way east before you could see a tiny speck of the others in the distance.

Lady D went on to win many more races and confrontations. She was known and respected throughout the Territory and soon her reputation spread in the region.

It is sad to say that it was her speed which led to her demise.

Sometime in the early 1950’s, a group of men from down island showed up at Haldane’s door inquiring after the sloop they had heard was so fast. They made him an offer he couldn’t refuse and were soon heading south towards Anguilla.

In those days, travel between the Virgin Islands and St Martin was made by way of the Anegada Passage from North Sound. A boat would leave at sunset and reach Anguilla by first light. It is still done that way today no matter which direction you are going; only today we use the Round Rock passage on the other side of Virgin Gorda.

It was dark and the new owners settled in for a long night of sailing. It is not known if they all went to sleep or if the man at the tiller wasn’t paying attention, but the Lady D was so fast that at 1am she ran full speed onto the reef in Anguilla, broke up and was a complete loss.

Haldane tried to build another one like her in his construction of the Lady May. The vessel was fast but nothing to compare to the Lady D; perhaps the fastest sloop ever built in these parts.

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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