Sometimes in Key West, people get that “sinking feeling.” Not because there’s anything negative about Key West — the Florida Keys’ southernmost island city features restaurants with great food, intriguing attractions to explore, world-class watersports, rollicking nightlife and a friendly, easygoing atmosphere.

Minimal Regatta Key West

A hapless contestant tries (and fails) to stay afloat during a past Schooner Wharf Minimal Regatta. (Photo by Rob O’Neal, Florida Keys News Bureau)

No, something else entirely causes them to get that “sinking feeling.” It happens each Memorial Day weekend when they compete in a very strange regatta — where, in the course of one wacky afternoon, many participating vessels simply disintegrate in the water, leaving their navigators dogpaddling like Gilligan when his “three-hour tour” went wrong.

Known as the Schooner Wharf Minimal Regatta, it took place this year (as always) off the Schooner Wharf Bar in the Key West Historic Seaport. Spectators lined the dock to view the antics — and it was pure maritime mayhem.

Before floating their boats, participating teams were first required to build them (no, I’m not kidding). And since the event is held in the Florida Keys, where locals pride themselves on doing things a little bit differently, the allowed construction materials weren’t exactly traditional.

In fact, team members had to construct an actual boat out of a single sheet of 4-by-8-foot plywood, two 8-foot-long 2-by-4s, a 60-yard roll of duct tape and a pound of fasteners.

Epoxy paint was permitted to decorate the quirky craft — and team costumes were encouraged. But using caulking or adhesives was strictly forbidden, adding to the already daunting fabrication challenge.

Schooner Wharf Minimal Regatta Key West

The intrepid captain of the mini Titanic goes down with his ship during the 2024 regatta. (Photo by Matthew Dockery, Florida Keys News Bureau)

Once the bizarre boats were built, it was up to the “designated captains” to steer them around a short course in the seaport faster than all rivals — without overturning or sinking.

During past regattas, even boats that looked about as seaworthy as cottage cheese somehow stayed afloat (possibly held together by their intrepid captains’ spirit alone). In 2024 as in the past, however, some captains got the aforementioned “sinking feeling,” and could only try to maintain their dignity as their crafts crumbled around them.

Whether the vessels stayed afloat or not, the event’s spectators seemed most impressed by the ones that displayed a heavy-duty dose of creativity.

The 2024 regatta’s standout entries included a miniature pirate ship with a mermaid figurehead, and a tiny Titanic replica that quickly capsized … while the strains of music from the “Titanic” film wafted through the seaport.

Speaking of creativity, few veteran spectators can forget a couple of past entries: a replica of Key West’s iconic Southernmost Point marker, which quickly overturned and dunked its captain, and a colorful rooster-themed vessel dubbed Chick Magnet in salute to the local free-range poultry population.

Key West's Minimal Regatta

An entrant paddles a rooster-themed vessel dubbed Chick Magnet during a previous Schooner Wharf Minimal Regatta in Key West. (Photo by Carol Tedesco, Florida Keys News Bureau)

In 2024 as in previous years, prizes were awarded for the fastest boats, most creative designs, best paint jobs, best costumes and sportsmanship. And the dreaded “sinker” awards were presented to the hapless teams whose vessels proved the least seaworthy.

Live music and a barbecue rounded out the afternoon’s action at the Schooner Wharf — a place where something is always happening, whether in the waters of the seaport or in the laid-back bar that’s a favorite hangout for locals.

Owner Evalena Worthington pays special attention to finding high-quality bands to grace the small stage. Overall, the Schooner Wharf is the kind of funky open-air emporium where you can bring your dog, your girlfriend and half a dozen fishing buddies — and everyone will have a good time (without evoking any “sinking feelings” at all).

Want to know more about the landmark bar and its packed calendar of only-in-the-Keys special events? Just click here.