Sept. 7/2023: While vacationing in West Cork, Ireland, last month, one of my goals was to spend some time sailing with Don Street. It says a lot that this is even a possibility. The last time I sailed with Don, when he was a sprightly sure-footed 75-year-old, was way back in 2005, aboard his famous 100-year-old yawl Iolaire. Since then he’d sold Iolaire, and the old girl, very sadly, was wrecked and lost by her subsequent owner on the coast of Ibiza in 2019.
So these days Don focuses on sailing Gypsy, his 86-year-old International Dragon. “She’s trying to catch up to me,” he noted with a grin as we rowed out to where the boat lay on her mooring in Glandore Harbour. Don has owned this boat for 38 years and likes to brag that she is the oldest Dragon still sailing, which very likely is true. I certainly have to believe he is the oldest Dragon sailor still sailing.
Don led me through a tour of Gypsy’s running rigging, which features a few creative touches only Don could have thought of, and also showed me where he keeps the ship’s “church key” (see photo up top), on a lanyard right by the helm. He produced a couple of Heinekens, and we settled down to discuss his career racing the boat.
Greenies in the bilge!
Don seated at the helm. In spite of some neglected cosmetics and antique gear, Gypsy is in very sound condition
Gypsy on her mooring, boasting a fresh coat of topside paint
A proud moment! Don racing Gypsy at the 90th anniversary Dragon class regatta in San Remo, Italy, in 2019. As Don describes it, all the Dragons, classic wood and modern fiberglass, some 160 boats, were mustered on one start line. He stayed clear of the mayhem, then took a huge flyer on one long offshore board out to the layline, as he felt he had the boat in a good groove. When he tacked back to the mark and called for a spinnaker set, he was surprised to find much of the fleet was behind him
Afterwards we rowed back ashore and spent some more time chatting in the sun room behind the small cottage where Don lives with his wife Trich, right next door to the Glandore Harbour Yacht Club, just a few footsteps from the waterfront. It is filled with memorabilia from Don’s long career afloat.
Iolaire’s Royal Ocean Racing Club pennant. Don claims it flew longer on Iolaire than any other RORC pennant on any other boat in the club’s history
From the cutting edge of electronic navigation in days gone by: a radio-direction finding kit
Souvenir photo from the ’87 Stars and Stripes America’s Cup campaign. Don’s son-in-law worked the foredeck
Painting commemorating Don’s appearances at the Brest International Maritime Festival—in 1992 aboard Gypsy, and in 1996 aboard Iolaire. The bird in the middle is a white-tailed sea eagle, or “iolaire” in Gaelic
Photo of Gypsy returning from Brest in 1992. Don sailed her there and back on her own bottom and fired off smoke flares as he sailed her triumphantly into Glandore Harbour
In the end, unfortunately, I didn’t get to sail with Don. He’s the first to admit he isn’t quite as sprightly and sure-footed as he was at 75. And when the forecast for that weekend’s GHYC Golden Cup event came in with a strong breeze gusting to better than 25 knots, he decided we better punt.
Still, I was super-impressed when I went to visit again a few days later and found him in his office in the cottage’s cramped attic, at the top of a very steep ladder.
Don in his office lair
His goal now, he told me, is to race Gypsy in the 100th anniversary Dragon class regatta in 2029, when he’ll be just one year shy of 100 himself. I assured him I’d be there to crew for him, if he’d have me.
For a thorough recap of Don’s long and illustrious career in sailing, I urge you to check out this article by Andy Schell that ran in SAIL a few years ago!
