Don Street Stories: A Rough Start in the Virgin Islands

Street in good company with sailors Paul Shard and Liza Copeland.

This is the third part in an ongoing series of short pieces that didn't make the final magazine cut of my 'Don Street is Not Dead' article. Some of the below appears in the magazine, but most of it's new. To listen to the entire 90-minute conversation I had with Don, click here. To kick things off, here's what outgoing Yachting World editor David Glenn said about Street when I prodded him last year...

"Don was always with his typewriter in what used to be the 'Last Lemming' bar in Antigua with his trademark, sweat stained Tilly Hat in place and a cold green 'un – i.e. a Heineken – handily placed, while he bashed out his next story. Seamanship is seamanship and he knows the meaning of the word and its importance, something that many modern yachtsmen don't! Don might be from another era but his thinking is still relevant. Worth dusting him down from time to time….!"

Without further ado, another Don Street Story...


Donald Street's legendary accomplishments in the Caribbean didn't happen immediately. In fact, from the stories he tells of the times, it’s a wonder he ever got anything accomplished.

Take for example his paint contracting business he and a friend started in St. Croix, an endeavor, Street admits, that “was not successful.”

He and his friend would work normal contracting hours – up early, start work at 7am and quit by 3. They’d end up in town by 4pm, ready for a cold beer. Problem was, the pub in town was run on traditional British pub hours – closed between 2:30pm and 5:30pm, when it would reopen for dinner. 

“Well, Robin was tall, and there were these little windows you could open up top,” Street explained, grinning all the while. “I’d stand on Robin’s shoulders, go through the window, open up the door.” Street had to pause here to laugh, his eyes smiling as much as his face. It was fun to watch the wheels turning in his head as he recalled all these obviously joyful memories. “And we’d start a tab. Various other people knew about this, and came knocking on the door [laughs] and we let them in, and Aubrey would show up at 5:30 and say ‘I’m the only guy who can make money with a pub when he’s sound asleep in bed!’”

Street bounced around the Virgin Islands doing various work to stay busy, but quite obviously enjoying himself, away from the cold concrete canyon of Wall Street, and in a place where nobody cared if he had a beard. 

His first ‘real’ work experience came as a land surveyor. “I didn’t know a damn thing about it,” he admits. “I bought on book on Friday, and by Wednesday had convinced them that I’d learned enough to do basic survey work and they hired me. I figured it was just like navigation, except you knew exactly how far you went!”