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We are a crew of dedicated sailors, ready to make your vacation a memory for a lifetime.

a man wearing sunglasses

Laurie Gumbs


Captain Laurie Gumbs was raised on the water. Born in Sandy Ground, Anguilla, Laurie grew up with the sea at his front door. He comes to sailing naturally as his father and many uncles were captains and sailors on some of the most historic Caribbean sailing vessels.

For Laurie, owning and captaining a vessel like Tradition has been a lifelong dream and given his sailing forefathers, perhaps even his destiny. He knows the history of the islands, has wonderful and engaging stories of the people, and great experience on the water.

A professional in the hospitality business (Laurie owns The Pumphouse, a world-famous restaurant and rocking roadhouse in Sandy Ground), Laurie knows how to treat his clients with excellent service and outstanding charm.

a person standing next to a body of water

Deborah Vos

Guest Services/First Mate

While growing up on a large grain farm in Northern Alberta, First Mate, Deborah Vos, was constantly filled with dreams of wind against canvas and a wide open sea. With no sailing opportunities in the wilderness of the North, Deborah took every opportunity to canoe, kayak and swim in the rivers around her home.

In 2008, her long held sailing dream became a reality when she joined the sail training tall ship, Picton Castle, for a year long circumnavigation around the Atlantic. Making the transition from pollywog to shellback, Deborah learned the ropes onboard a traditional tall ship and never looked back.

She fell in love with blocks, with lines, with the pure joy of hauling sail. While modern yachts have some appeal, Deborah’s heart is with classic boats like Tradition.

a person standing next to a body of water

Thomas Maccow Jr.


When we first met Thomas eight years ago, he was a student at the Anguilla Youth Sailing Club. We watched his sailing skills progress and cheered him on as he competed in dinghy regattas, laser competitions. Before we knew it, he was teaching younger children how to sail, and soon became the Assistant Director of the AYSC.

We couldn’t have been more delighted when he joined us as crew on Tradition. His passion for sailing is evident every day. His commitment to the daily set up and tear down of the boat is inspiring.

Best of all, his quiet and thoughtful interactions with our guests is absolutely lovely. A shy guy with a great smile and a commitment to ensuring everyone on board has an unforgettable day. In 2021, Thomas moved up the ranks after completing his Boatmaster Certificate and you’ll now often see him handling the helm with ease and confidence.