Ship of Fools

A hilarious annual regatta turns Jamestown’s shore into a seafaring spectacle


It’s a beautiful Saturday morning and you’re sailing up the bay. Jamestown is on your port side, Newport to starboard, and the Claiborne Pell Bridge looms ahead. You’re tracking the other boats on the water, but then you do a double-take toward the Jamestown shore. You see a boat, if you can call it that, made from plastic storage boxes – the kind you keep in your basement – connected by two-by-fours with giant plastic flowers for sails. Right behind it are three young women barely staying afloat on an enormous plastic bag filled with exercise stability balls and a clear plastic tarp for a sail.

Welcome to the Jamestown Yacht Club’s annual Fools’ Rules Regatta. This year’s event, scheduled for August 10 on the Town Beach, East Ferry, will be the 42nd race. The regatta typically draws 25 to 35 entries, mostly from New England, but sailors from California, New York, and Pennsylvania have also participated says Greg Hunter, who became the race’s Chief Fool in 2018. Greg started as a spectator in the late 1980s and began participating with his brothers. Since then, he has been involved in the building, sailing, and sinking of multiple vessels with his children, other family members, and friends.

This obviously isn’t your typical regatta. Each craft must be made from non-marine items only, and participants get two hours before the race to assemble their boat on the beach. Those rules lead to some hilarious and clever design innovations. Greg has seen a double-decker boat with a loveseat stacked over a sofa – a design that finished first in its class, he adds. Other noteworthy efforts have included a 25-foot catamaran that used cardboard construction tubes, balloons, and netting for a sail; another was made from water bottles.

Racers compete for prizes based on crew size, with special awards for best and worst designs, including The Karl Smith Most Ingenious Design and The Worst Example of Naval Architecture. Anyone can enter the race provided they bring a life jacket, an anchor for their boats, and a willingness to be foolish.