It’s not always easy to stay afloat. And that’s particularly true if the vessel you’re piloting is made of nothing more than a 4-by-8-foot sheet of plywood, two 8-foot-long two-by-fours, a 60-yard roll of duct tape, a pound of fasteners and a daub or two of epoxy paint.

Minimal Regatta Key West

A contestant tries (and fails) to stay afloat in the 2022 Schooner Wharf Minimal Regatta. The “sink or swim” regatta takes place in the waters off Key West’s Schooner Wharf Bar. (Photo by Rob O’Neal, Florida Keys News Bureau)

Keeping their plywood-and-duct-tape boats afloat is the mission for the valiant teams in the annual “sink or swim” Schooner Wharf Minimal Regatta — a wacky annual event that has been a Memorial Day weekend tradition in Key West for more than 30 years.

Naturally, the homemade crafts’ minimal construction means marginal seaworthiness. And that, in turn, means maximum hilarity for the many hundreds of spectators who line the waterfront at the island city’s Historic Seaport each year to watch the aquatic antics.

Team members in the challenge navigate a short course in the seaport area, trying to avoid sinking long enough to complete it — with varying degrees of success. Up to six members are allowed per team, and at least one stalwart “sailor” must stay aboard the vessel throughout the regatta.

Some teams get “that sinking feeling” soon after launching, including (on one memorable occasion) a hapless group that constructed an outrigger mistakenly named No Problem.

Sinking standouts in recent regattas have included a tiny Tiki hut that overturned midcourse and an unsteady entry whose captain, costumed as a park ranger, nobly went down with his ship.

Other vessels in the annual spectacle remain surprisingly buoyant — and many sport clever designs that illustrate their builders’ imagination and construction skills. Epoxy paint is permitted to decorate the makeshift boats (though calking and adhesives are not) and team themes and costumes are encouraged.

Unforgettable past entries have included a red-and-white striped creation whose paddler portrayed the children’s book character “The Cat in the Hat,” a tiny replica pirate ship with furled sails that carried a costumed buccaneer, and a floating miniature golf course.

Minimal Regatta Key West

Hapless mariner Sean Blaise goes down with his ship during a past Minimal Regatta. (Photo by Carol Tedesco, Florida Keys News Bureau)

And one year, “Gilligan” himself navigated a tiny replica of the S.S. Minnow from the classic sitcom “Gilligan’s Island,” cheered on from shore by teammates costumed as the show’s iconic Skipper, movie star Ginger and perky Mary Ann.

The 2023 regatta is to take place Sunday, May 28, in the waters off the Schooner Wharf Bar. Teams typically line up on the lane behind the popular bar in late morning, making last-minute improvements to their craft and adjusting costumes to avoid potential wardrobe malfunctions.

A vessel inspection is scheduled for 12:30 p.m. Sunday. The first heat is to begin about 1:30 p.m. and continue until all entries have made their way (or not!) around the course.

While spectators must sometimes watch their favorites sink beneath the waves, the event’s lighthearted fun and seafaring spirit generally outweigh any disappointments. The revelry also includes live music and a Memorial Day weekend barbecue at the Schooner Wharf.

Of course, even the quirkiest regatta wouldn’t be complete without prizes. The intrepid winners in the Minimal Regatta can anticipate plenty of them — to be awarded in categories including the fastest boats in the kayak/canoe and open design divisions, the best paint jobs, most creative designs, sportsmanship and the best costumed entries.

But in this crazy challenge, winning a prize isn’t as important as avoiding a prize: the dreaded “sinker” awards that go to the LEAST seaworthy vessels.