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David Wegman: High Seas Wanderer

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One of the reasons that I love the cruising life is because I often cross tacks with people who are … well … you know … different. Take for example my friend David Wegman. He knew Jimmy Buffett before he was famous, and even occasionally plays music with him. David is not just a friend of the legendary Foxy Callwood, on Jost van Dyke in the British Virgin Islands; he sculpted the statue that greets the visitors to his sandy saloon. And not only can Monsieur Wegman get a table at Le Select in St. Barts, he has an art studio above the bar.

David Wegman in Key West
David Wegman in Key West

His seafaring life began in Key West in the early 1970s when it was a laid-back haven for artists, musicians, and smugglers. His first sailboat had character and history. Thirty people crowded onto this engineless 30-foot sloop and made the treacherous crossing from Cuba to America. They got their freedom and David got a stalwart boat for only $1,000. She had quite a name – AFRIGAN QUEEN II. Either the previous owner misspelled ‘African’ or had issues with queens.

For his 25th birthday, David decided to sail out to the Dry Tortugas islands. A friend joined him for a fun-filled week. Unfortunately, Hurricane Agnes formed suddenly and plundered Florida. Somehow David and his mate managed to survive 100 knot winds for what seemed like an eternity. Using buckets and pots they bailed out the boat around the clock. Ten days after leaving Key West they spotted the Gulf Coast of Florida, and ran the brave little sloop onto the beach.

The World of David Wegman

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Awaiting them was a stunning apparition—a shiny black hearse and a man dressed in a shiny black suit. Fortunately, it was not the Grim Reaper, but a city councilman from Venice, Florida, who also worked in the town mortuary. He was surveying road damage, and spotted the wounded sloop staggering ashore. He loaded the exhausted but elated survivors into his hearse and drove to the mortuary where he gave them some dry clothes purloined from an undisclosed source.

This was the first of many gestures of kindness that the local citizens showered upon David. Because they had also suffered the wrath of Hurricane Agnes, they were astonished that anyone in a tiny boat could survive such fury out in the Gulf of Mexico. After their saga made the front page of the local newspaper, many curious townspeople brought David food, tools and encouragement.

The artist with one of his paintings
The artist with one of his paintings

The effort to refloat the little wooden boat became a community crusade and nearly a circus act. Ringling Brothers had their winter quarters nearby and they tried to organize a rescue effort that would utilize two big slings and four even bigger elephants to walk the sloop back into the sea. After about ten days ashore, a bulldozer and an abnormally high tide returned the stranded sloop to her saltwater element. Sadly, she craved that water too much, and the pumps could not stay ahead of the leaks. David ran her back onto the beach and removed everything of value. Then he burned the valiant little boat and shoveled the ashes into a dumpster, which he jokingly referred to as a “large urn.”

The silver lining to this sad tale was that by losing his boat, which was also his home, David qualified for hurricane assistance, so he took the $2,500 check. Here, any sensible person would have sworn off the sea forever, but not Hurricane Wegman; he went searching for his next dream girl.

In the Chesapeake Bay area he found a fine little Dutch-built sloop that even had a functioning one-cylinder diesel engine. Soon, AFRIGAN QUEEN III was heading south towards Key West on the Intracoastal Waterway. His next beyond the horizon destination was the Bahamas. Imagine how unspoiled those sunny isles must have been in the early 70s. That voyage convinced David that life as an ocean vagabond would be just fine with him.

As more distant islands beckoned, his second sloop found her bow heading for the fabled West Indies and a voyage all the way down the chain to Trinidad. At that point he ran into a continent, so he headed back up the W’indies, revisiting favorite spots and exploring new ones along the way. Around this time, he discovered Coral Bay on St. John in the U.S. Virgin Islands. The kickback community there felt just about right.  The fact that the nearby mangroves also provided excellent hurricane protection convinced him to make this his new home port.

Around 1982 David bought the hull and plans for a Block Island Schooner. He spent a couple years on St. Thomas transforming the empty fiberglass shell into a handsome, any-ocean 40-footer. With his new vessel, it was time for a circumnavigation.

He left St. John in 1990 and went through the Panama Canal and out to Cocos Island, then the Galapagos, on to the Marquesas and Tahiti.

Friends joined him for many of the legs and sometimes he single-handed. He negotiated the dangerous Torres Straits, crossed the Indian Ocean and sailed on to South Africa. In 1998 he completed his voyage back in St. John.

I’ll close with a wonderful example of David’s eccentricity. He has a hammock on his schooner—but it isn’t mounted above the foredeck or between the masts— it is rigged beneath the bowsprit so that he can be within tickling range of those kindergarteners of the sea, the playful dolphins.

Ray Jason is the author of the humorous, offbeat sailing book Tales of a Sea Gypsy. He’s still out there happily wandering the oceans in his lovely 30-footer.

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  1. Today, Feb 15, 2017, my husband was fishing in Coral Bay in the shallows, early morning across from Calabash Market. Up floated a picture…named “Gone Fish’n” and it is signed by David Wegman. I have a photo of it if David would be interested in seeing it. It’s actually in awesome shape and it’s hanging on our wall!!


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Ray Jason
Ray Jason
Ray Jason is the author of the humorous, offbeat sailing book Tales of a Sea Gypsy. He’s still out there happily wandering the wide waters in his lovely 30-footer. 

So Caribbean you can almost taste the rum...

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