Story and photos by David H. Lyman
A friend has died, and with him goes a great deal of Caribbean sailing history. The sailing community will miss him, but his passing was enviable. Don Street — navigator, boat owner, charter skipper, racing sailboat driver, mentor, prolific guidebook author and magazine writer — was sailing to the very end.
News reached us via a post from the Glandore Harbour Yacht Club in Ireland, where he has lived with his wife Trich for 30 years. He leaves behind a daughter and three sons: Dory, Donald, Richard, and Mark.
There was nothing about boats, the sea, or the West Indies that Don did not have an opinion on. He’d been sailing, charting, and chartering in these islands for more than 50 years aboard his engine-less wood yawl, Iolaire.
I first met Don at Antigua Race Week in 1984. I photographed him, his six-year-old son Mark atop his shoulders, when he went up to claim his prize for winning his division (see pic below). The next day, I paid Don and Iolaire a visit. They were tied to the quay at Nelson’s Dockyard in English Harbour. Don’s yacht was showing her years. The patchwork decks were a checkerboard of various woods; the sails were old and tarnished, and the tiller was well worn. Crew were scurrying around, putting things to right, with Don sitting at the helm, barking out instructions. What I realized then, and know now, is that new gear, fancy electronics, carbon sails, chart plotters, and GPS will not replace experience and knowledge.
Later, when I was writing for the magazines, I’d occasionally get a note from Don, or he would back me up on some nautical point in a letter to the editor. Those words of encouragement from him meant more to me than did the checks from the publisher.
Don was one of those larger-than-life characters you’ll find in the tropics. He was an authority on everything dealing with offshore passage-making, proper yacht design, and sailing among the islands of the Eastern Caribbean. As a fellow maritime writer, I will miss our monthly conversations via email, collaborating on articles. I’d ask him to comment on a paragraph I’d written, some aspect of navigation, and I get back three pages of his informed opinion. I’d write back, “Just the facts, Don, just the facts, please.” We’d discuss (argue) about anchors, anchoring techniques, routes to and between the islands, and hurricane preparations. He knew what he knew, and he didn’t mind sharing that knowledge with anyone who would listen.
Sitting at Pusser’s Landing in Soper’s Hole on Tortola in the 1980s, I listened as Don monopolized the conversation with a Greenie — a bottle of Heineken — in hand, and in his high-pitched voice (his nickname was “Squeaky.”) I listened to him berate a poor skipper who had the misfortune to run his boat onto a rock that Street had purposely charted in his guides.
Thankfully, there are still half a dozen of his books to read and reread. They remain valuable references, even those that are out of date and out of print, for, as Street is quick to point out, “the bars and services ashore may change from season to season, but the rocks and reefs haven’t moved in a hundred years.”

















