Every day is an adventure in the Florida Keys, where the subtropical climate and scenic natural setting create the perfect backdrop for high-energy activities. You can experience watersports and eco-adventures, unparalleled offshore diving, and organized sporting challenges to test your endurance — but also enjoy a little wackiness while you’re at it. So put one (or all!) of these “only in the Keys” events on your bucket list.
Competitors in the open-water Swim for Alligator Lighthouse round the base of the historic Upper Keys beacon. (Photo by Andy Newman, Florida Keys News Bureau)
Each April the Seven Mile Bridge Run, a nearly 40-year-old foot race over the convergence of the Atlantic Ocean and Gulf of Mexico, temporarily closes the world-famous Seven Mile Bridge — the longest of 42 spans on the Florida Keys’ Overseas Highway. Slow runners in the iconic race risk being collected by the sweep bus, which picks up racers who don’t keep a steady pace, creating a lighthearted “beat the bus” vibe.
Paddleboard and self-propelled watercraft fans can participate in a renowned competition, too: the 12-mile Key West Paddle Classic, a race around the United States’ southernmost island, which usually takes place in May.
And let’s not forget the Key West Island Swim: FKCC Swim Around Key West, held each June — a 12.5-mile clockwise swim around the entire island. Individuals and relay teams can compete. The route takes swimmers through the waters of the Atlantic and Gulf of Mexico, ending where they began at Smathers Beach.
Islamorada’s 8-mile Swim for Alligator Light, generally held each September, raises awareness about the need to preserve the Keys’ aging offshore lighthouses — while offering challengers a unique fast-paced swim in open ocean waters.
Every July, the Lower Keys Underwater Music Festival entertains divers and snorkelers during an “only in the Keys” underwater concert to promote reef protection. The intriguing event takes place at Looe Key Reef, part of the Florida Keys National Marine Sanctuary approximately 6 miles south of Big Pine Key. The sanctuary protects the waters surrounding the entire Florida Keys island chain, including the continental United States’ only living coral barrier reef.
Costumed characters pretend to play a sculpted conch shell and “saxophone” beneath the sea at the Underwater Music Festival. (Photo by Bob Care, Florida Keys News Bureau)
An offbeat festival that commemorates the Keys’ symbolic secession from the United States (yes, really!) is staged each April. The Conch Republic Independence Celebration recognizes the republic, which was born following a 1982 U.S. Border Patrol blockade of the island chain.
In protest, citizens organized the secession, declared war on the mother country, surrendered 60 seconds later and demanded $1 billion in foreign aid. The anniversary of the secession is marked each year with a roster of eccentric events.
The best known “only in the Keys” event is undoubtedly Fantasy Fest. Key West’s 10-day extravaganza takes place every October — and attendees can anticipate creative costuming, offbeat artistry and exuberant adventures for masked and costumed revelers.
The themed festival features several dozen masquerade balls, costume contests, exotic parties and showcases for quirky creativity, all climaxing in the lavish Fantasy Fest Parade.
There’s also an event that takes place every single evening in Key West: the waterfront Sunset Celebration, named America’s best free attraction by TripAdvisor. For nearly 40 years, the sunset “carnival” at Mallory Square has drawn large crowds to applaud the talents of colorful street performers, view artisans’ handmade wares and watch the sun sink beneath the horizon beyond Key West Harbor.
A tightrope walker, jugglers, fortunetellers and musicians are among the attractions — as are local artists selling items ranging from jewelry and hand-painted T-shirts to photography and paintings.
In fact, no matter what time of year you visit the Florida Keys, you’ll find energetic adventures and high-spirited happenings that merit a spot on your bucket list. To check out the full calendar of Keys events, just click here.
