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The Florida Keys are known for turquoise waters, swaying palms, and that laid-back island lifestyle. But if you look a little closer, you’ll find something else the Keys do better than anywhere else: quirky fun. From a giant lobster statue in Tavernier to a full-fledged turtle hospital in Marathon, this island chain is bursting with weird and wonderful surprises.
So, if you’re planning a road trip down U.S. 1, here are the top quirky Florida Keys attractions — in order — from Key Largo to Key West.
1. Cruise on The African Queen (Key Largo)
Looking for one of the most unique things to do in Key Largo? Step aboard The African Queen, the actual steamboat from the 1951 Humphrey Bogart and Katharine Hepburn film. She’s still afloat, chugging through the canals with her iconic whistle. It’s part sightseeing tour, part movie magic.
Local Tip: After your cruise, grab a cocktail at Skipper’s Dockside, right on the water.
2. Say Hello to Betsy the Lobster (Tavernier)
Searching for quirky photo spots in the Florida Keys? Look no further than Betsy, a 40-foot-long fiberglass lobster outside Rain Barrel Village in Tavernier. She’s massive, clawed, and endlessly Instagrammable. Behind her, the open-air art village is filled with colorful Keys-inspired crafts.
Local Tip: Wander through the hidden garden paths — you’ll find murals and sculptures most tourists miss.
3. Dive into History (Islamorada)
Islamorada may be famous for sportfishing, but one of its coolest attractions is the History of Diving Museum. With antique helmets, deep-sea suits, and tales of treasure hunters, it’s a fascinating look at humans’ obsession with the ocean. It’s a must-see if you’re looking for indoor things to do in Islamorada.
Local Tip: After your visit, head to Florida Keys Brewing Co. nearby — it’s colorful, funky, and perfect for a post-museum pint.
4. Visit the Turtle Hospital (Marathon)
One of the most heartwarming Florida Keys attractions is in Marathon: The Turtle Hospital. This working facility rescues, rehabilitates, and releases injured sea turtles. Tours let you meet patients with names like Bubble Butt and learn about their recovery.
Local Tip: Book your spot early, especially in peak season — tours fill quickly.
5. Walk the Old Seven Mile Bridge (Marathon)
For some of the best free things to do in Marathon, take a stroll or bike ride on the Old Seven Mile Bridge. The views are endless — turquoise waters in every direction — and the sunsets rival Key West’s famous Mallory Square (without the crowds).
Local Tip: Bring water and a hat — there’s no shade, but the breeze makes up for it.
6. No Name Pub (Big Pine Key)
If you’re craving quirky dining in the Florida Keys, No Name Pub delivers. Tucked away on Big Pine Key, this legendary spot serves pizza and cold beer under ceilings covered with stapled dollar bills — nearly $90,000 worth!
Local Tip: Drive slow — the endangered Key deer roam freely around Big Pine.
7. The Underwater Music Festival (Big Pine / Looe Key Reef)
Looking for the most unusual events in the Florida Keys? Each July, divers and snorkelers head to Looe Key Reef for the Underwater Music Festival. It’s broadcast through submerged speakers while costumed “musicians” pretend to play under the sea. Equal parts surreal and silly, it’s an only-in-the-Keys experience.
Local Tip: Bahia Honda State Park is the perfect dry-land spot to catch the music and enjoy the beach.
8. Roaming Roosters (Key West)
When you arrive in quirky Key West, you’ll immediately meet its loudest residents: the roosters. Protected by city ordinance, they strut across Duval Street, crow at all hours, and add plenty of feathered personality to the island.
Local Tip: Sip a Cuban coffee at Cuban Coffee Queen — the roosters will likely wander by to join you.
9. Hemingway Look-Alike Contest (Key West)
Held every July at Sloppy Joe’s, this Key West tradition brings dozens of white-bearded men competing to be crowned the best Ernest Hemingway look-alike. It’s hilarious, a little chaotic, and one of the quirkiest festivals in the Keys.
Local Tip: Visit Hemingway’s Key West home year-round, where six-toed cats lounge in the gardens like they own the place.
10. Join the Conch Republic (Key West)
In 1982, Key West “seceded” from the U.S. to protest a border patrol roadblock, creating the Conch Republic. Today, it lives on with its own flag, passport, and annual April festival full of parades and sea battles. It’s Key West’s quirky spirit at its finest.
Local Tip: Stop by a local shop for a Conch Republic flag or passport — the ultimate quirky souvenir.
Final Thoughts
From movie boats in Key Largo to roosters in Key West, the Florida Keys are full of quirky attractions that make any road trip unforgettable. Whether you’re looking for fun things to do in the Upper Keys, hidden gems in Marathon, or eccentric festivals in Key West, you’ll find stories worth telling for years to come.
