8 Quirky Things to See on a Florida Keys Road Trip

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If you’ve never rented a car or RV and hit the road in the direction of America’s own Caribbean-inspired escape, you’re in for a multitude of surprises. Aside from palm trees jostled by the breezes and baby blue water as far as the eye can see, the Keys have a fun, quirky personality unlike any other found in the entire nation. So it’s no wonder that this chain of tropical islands is bursting with offbeat, eccentric, and downright strange things to do and see. We’ve rounded up a few oddball places you shouldn’t miss on your Florida Keys road trip. 

1. The 17th Century Cannons Guarding Cannon Beach in Key Largo

Cannons on the beach

Key Largo is the official starting point for a Florida Keys road trip, and it also happens to be one of the best spots in the region for snorkeling, thanks to the country’s first undersea sanctuary, the John Pennekamp Coral Reef State Park. The parts of the park on land include Cannon Beach, a man-made beach with a very special feature: two 17th century cannons nestled along its shore. These cannons originally belonged to the HMS Winchester, a British man-of-war ship that met its unfortunate end in a shipwreck back in 1695. Recovered by salvagers before the area was a National Marine Sanctuary, these relics are a shout out to the Keys’ maritime past.  

After you check out the cannons, make plans to snorkel near the Spanish shipwreck replica just a hundred feet offshore. 

2. The Steamboat That Got Top Billing in a Classic Movie

African Queen steamboat in Florida KeysImage: AP Photo/Florida Keys News Bureau, Andy Newman

For years, the African Queen has lured old romantics eager to experience even the shortest trip on this legendary vessel, a steamboat built more than a hundred years ago. One of Key Largo’s top attractions, it’s famous for its starring role in the 1951 film “The African Queen,” a classic featuring Humphrey Bogart and Katherine Hepburn. 

The steamboat, now a National Historic Site, enjoyed a long life of service in Africa before being brought to the United States and put to use in California, Oregon, and Florida. Nowadays she shuttles lucky passengers on cruises around the Port Largo Canal area and is also available for private events (for those hopeless romantics among us). 

3. The Slightly Creepy Exhibits at the History of Diving Museum

Scuba exhibit at diving museum.

Diving has come a long way, judging by the extensive exhibits at the History of Diving Museum located in Islamorada. It’s home to a vintage collection of diving helmets, armored suits, and other early-stage diving equipment, along with photos and memorabilia related to humanity’s first undersea explorations (some more successful than others). 

Walking through the museum and confronting peculiar diving suits gives you a slightly unsettling feeling, especially since they give off old-school sci-fi or horror movie vibes. Nevertheless, you’ll be impressed by the story told through the collection, passionately collected by Drs. Joe and Sally Bauer, who wanted nothing more than to share with the world the many historical items they curated from around the world. If you’re into exploring the underwater world, there’s a lot to learn here — it’s a must-visit on your Florida Keys road trip. 

4. Betsy, the World’s Largest Lobster

Big Betsy

It’s hard to miss Betsy as you’re driving along the Overseas Highway in Islamorada. Dubbed the world’s largest lobster, she’s a 30-foot tall, 40-foot long sculpture guarding the entrance to the Rain Barrel Village in Islamorada. 

After you get over the shock and wonder of seeing Betsy close up, venture through this artsy village full of studios selling arts, crafts, and home goods. Enjoy the beautiful gardens and the bohemian ambiance, and take it slow. That’s what a Florida Keys road trip is all about! 

5. The Faro Blanco Lighthouse

Faro Blanco lighthouse

Standing at the heart of a scenic marina in Marathon, the Faro Blanco (“White Lighthouse”) has an interesting past. It was built in the 50s as part of a local motel, and at one point it did actually contain a light and functioned as a navigational aid.  

It was pummeled by a few hurricanes over the years, including Wilma, which delivered its worst beating yet. In 2014, the lighthouse was rescued from disrepair when the property was revamped to include the restaurant, yacht club, and marina. Since then, this white-and-red landmark has become the perfect spot for selfies and sunset photos.

6. The Old Bahia Honda Bridge

Image: Bob Krist/Florida Keys News Bureau

Astounding blue water. Bone-white sand. And in the background of this dazzling tropical panorama, an old rusted behemoth arching across the sky. The Old Bahia Honda Bridge, unmissable as you pass through Bahia Honda Key, is a remnant of the Overseas Railroad built by Henry Flagler in 1912. 

Flagler had high hopes that Key West would be Florida’s premier port city, though that never came to pass. Even worse, the railroad was all but destroyed in the Labor Day Hurricane of 1935, leaving it essentially out of commission. A portion of the Overseas Highway that was built over the top of that old railroad is all that remains of this relic. It lends a dramatic aura to the otherwise peaceful landscape. 

7. The Rum Distillery That Nods to “Bad Bitch” Spanish Marie

Barrels stacked at distillery

Distilling rum was illegal for the longest time in the Florida Keys, but luckily tourists can now openly and freely enjoy this island-inspired spirit. The hands-down best place to do that is the Key West First Legal Rum Distillery. Rums of various flavors are made on-site using a special distilling and aging process that involves salt cured barrels and Florida demerara sugar instead of molasses. 

Though you can try a variety of flavors (all excellent) the real standout is Bad Bitch, named for infamous Spanish Marie, a local rum runner who smuggled rum from Cuba to the Keys back in the day. She preferred her rum with a splash of red wine, so to honor her memory, her namesake rum is aged in French Oak barrels that once contained red wine. Cheers! 

8. The Birthplace of Pan American World Airways

Birthplace of Pan American

Pan Am is a distant memory for today’s fliers, but at one point the airline had grown to be one of the largest and most innovative airlines in the country. And it all started in the heart of Key West at what is now the First Flight Island Restaurant & Brewery at the corner of Whitehead and Caroline. This building is where the first tickets for flights between Key West and Cuba were sold in 1927. 

As a nod to the building’s history, the restaurant and brewery is adorned with Pan Am logos and other flight-related memorabilia, including a sea plane diving nose-first into Crash Bar, named for obvious reasons. Aside from fantastic food, this bar also boasts three unique brews made in-house and a beautiful, overgrown patio for relaxing with a drink under lush greenery. 

Before you set out to visit some of these places during your own Florida Keys road trip, be sure to take a look at the hotel, flight, and car rental deals from our partners. 

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