The first time Bruce Dyson laid eyes on his boat Gypsy, it could barely be considered a boat. Pulled from the bottom of New York Harbor, the International One Design’s deck was destroyed, the first four feet of bow was missing along with the transom, the mast was broken and there was a hole in the port quarter “that you could walk through.” It was a victim of what became known as the “Perfect Storm” in 1991 but Bruce saw something in the boat that made him think he could bring it back to life again.

“I determined it was repairable as the lead keel was fine,” he said. 

Many of his fellow Marblehead, Massachusetts, sailors weren’t quite
as optimistic.

“It was the laugh of the town. ‘Bruce’s going to fix it?’ Well, I fixed it and now it’s the fastest boat in the Marblehead IOD fleet.”

Having determined that because the boat had 10 ribs and a keelson that were in good shape it was “a good boat to start with but I need to get it to float,” Bruce spent a winter rebuilding the boat, which included replacing the missing bow, deck beams and deck and sistering about 20 frames. Then he replanked most of the port quarter. He used a solid piece of mahogany on each side of the boat and the back of the cockpit to replace the coamings and cabin sides. New floorboards and a mast step were also required. 

“Then I sanded and varnished the interior of the boat, installed all new deck hardware, found a mast and a boom, acquired sails, painted, launched and raced it,” he said, making the whole process seem much easier than it certainly was.

That shell of boat-turned-race winner became Gypsy, so named because Bruce didn’t have a mooring in Marblehead’s harbor, and the boat would move around to any free mooring he could find. 

The International One Design is a fine daysailer but it is primarily used in one-design fleets, where strict class rules and a healthy class organization make it the home of fun, competitive racing, at which Bruce, the 1998 class world champion, excels. He sails Gypsy out of Eastern Yacht Club in Marblehead and has traveled with the boat to big regattas like the IOD World Championship.

But it’s not the quest for a trophy that makes sailing Gypsy such a pleasure, Bruce said.

“Sailing that boat wouldn’t be half as much fun without the people on that boat and the tales they bring,” he said. 

His longtime crew consisted of what he described as “a cast of characters, one more entertaining and interesting than the next.”  They included sailmaker Norm Cressy, Bernie Coyle, David Hooks and Sue Foight.

In fact it’s friends and crew like those who are part of a perfect day of sailing, he said, although the competitor in Bruce also pictures a perfect day at the front the of the fleet.

“Getting three other people who are all great friends onboard, getting a great start, getting the lead, maintaining the lead and then stretching the lead. And a nice, cold beer on the way in is always nice,” he said.

Although the benefits of sailing in a well-run one-design class are certainly part of the IOD’s charm, Bruce’s love for Gypsy starts with her traditional design and is buoyed by her story of coming back from the dead. Although wooden boat ownership is not for the faint of heart and requires a steady amount of ongoing maintenance, Bruce said that the compliments he receives on how well she is maintained and how nice she looks, not to mention how fast she is, make the effort worth it.

Gypsy’s owner does have a certain knack for rebuilding and maintaining IODs. He’s owned four others and restored eight more over the years and along the way the man who was laughed at for trying to rescue a shell of a boat became known as the IOD Whisperer. When a hurricane damaged 12 IODs in Bermuda several years, the IOD Whisperer was flown in, housed and given all the materials he needed to repair all 12 boats in six weeks, living up to
his moniker.

Bruce and Gypsy have a long history together. There have been other boats, but for Bruce, Gypsy remains “the one.”

“It’s fun to sail and beautiful to look at,” he said. “What more does a boy need?”