Five Funky Things To Do in the Florida Keys

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Are you looking for funky things to do in the Florida Keys? While there are plenty of fun activities in the Keys, some are more unique than others.

On a Florida Keys road trip, as a guest of The Florida Keys and Key West, I expected to indulge in tasty seafood, treat myself to key lime pie, appreciate early American history, go charter fishing and photograph numerous sunsets. While I enjoyed all of this and more, what I didn’t expect to find were the fun choices of Florida Keys attractions that are available to visitors.

If a Florida Keys road trip is on your bucket list, don’t rush through this iconic trip for boomer travelers. Take your time to enjoy some quirky fun that brings back memories of rolling down the highway with the windows open, ocean breezes blowing through your hair, and the time to stop at every sight that piques your interest.

Key Largo: Cruise on the African Queen

boat travels down a canal in Key Largo, Florida
Looking across the bow of the African Queen. Movie history, here I come.

Thirty-three-mile-long Key Largo is the first key in the Florida Keys chain. And it’s only a 60-mile drive from the Miami airport.

Known as a diving mecca due to the longest artificial reef in the world, the 510-ft USS Spiegel Grove, Key Largo is also home to John Pennekamp Coral Reef State Park.

But I arrived on Key Largo intent on experiencing some quirky fun on the African Queen. How many film buffs can say they cruised on a movie set?

When Captain Lance Holmquist stokes the steam engine of the original vessel used in the movie, The African Queen, I channel my inner Katherine Hepburn. The famous Hollywood actress joined movie icon Humphrey Bogart in the 1951 film based in Africa’s Congo. The steamboat, also known as the African Queen, could certainly be considered a co-star.

As the boat lurches slowly along a canal in Key Largo, Captain Lance shares stories from the making of the movie. It’s a noisy endeavor what with the chug a chug chug of the engine and occasional shrill shrieks as Capt. Lance blows the African Queen’s whistle.

Florida Keys visitors can experience the African Queen on a 1.5-hour journey through Key Largo’s canals to the Atlantic Ocean and back. Or book a 2-hour dinner cruise that stops at Pilot House Restaurant for a 3-course meal.

Plan your trip to Key Largo

Islamorada: Feeding a tarpon is definitely one of the funky things to do in the Florida Keys

Islamorada is actually six islands (or keys) that together claim to be the “Sports Fishing Capital of the World.” I caught my first Florida fish here, but feeding a tarpon wins for my funkiest Florida Keys experience.

man feeding a tarpon fish in Islamorado Florida
Feeding tarpon at Robbie’s Marina in Islamorada, Florida

I never thought I’d be kneeling on a dock holding a slimy fish so that another fish with a great big mouth could eat it. But that’s exactly what I’m doing at Robbie’s Marina in Islamorada, Florida. Actually, I’m feeding one of 100 tarpons that hang around this special Florida Keys spot where Florida Bay meets the Atlantic Ocean.

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After throwing a bait fish into the water to attract the tarpon—also known as silver king—I kneel on the dock, holding a fish between my thumb and finger and wait. A tarpon jumps to grab the tasty morsel; I squeal and let the bait fish go. It misses the tarpon’s mouth but is quickly snapped up by another fish.

For $1 dock admission and a $3 bucket of fish, you, too, can squeal when feeding the tarpon.

sea shells in a shopping display in Islamorado, Florida
The funky shops at Robbie’s Marina in Islamorada, Florida

Feeding tarpon isn’t the only attraction at Robbie’s Marina. Enjoy browsing the mix of art, crafts and kitsch at the open-air shops scattered around the grounds before relaxing with a cool drink and Caribbean inspired meal at The Hungry Tarpon.

Stay longer in Islamorada

Marathon Key: Walk with Florida Keys history on the Seven-Mile Historic Bridge

Marathon is considered to be the “Heart of the Keys.” Visiting the sea turtles at the Turtle Hospital is one of the most popular, and rewarding, activities on this key that feels more like a small village. In fact, the Turtle Hospital is so popular that making a reservation is highly recommended.

Another must is walking the Seven-Mile Historic Bridge.

Seven-Mile Historic Bridge sign surrounded by trees in the Florida Keys
It’s a beautiful day for walking the Seven-Mile Historic Bridge

A Florida Keys road trip on the Overseas Highway is meant for taking it slow and enjoying the scenery. Be sure to get out of the car at the Seven-Mile Historic Bridge for a walk on a span of concrete that’s now on the National Register of Historic Places. Visitors and locals walk, bike, rollerblade or run the 2.2 miles portion of the bridge that’s open to recreationalists.

Pavement stretches out on seven mile bridge in Florida Keys
Walking with history on the Seven-Mile Historic Bridge

Walking beside Florida Keys history—the bridge was originally part of Henry Flagler’s railroad that connected Miami to Key West—I peer over rusted highway rails and down into the clear water of the Gulf to look for sea life, including sharks. Next time, I’m planting my  beach chair on the bridge in the late afternoon to watch the sun cast an orange glow across the water.

Slow down in Marathon for a while

Key West: Sunset Celebration at Mallory Square

When driving the Overseas Highway in Florida, Key West is the official end of the road. A favorite bohemian hot spot, and port stop for cruise ships, the southernmost city in the continental United States offers an abundance of quirky fun. Check out two of my favorites:

What’s funky about a Florida Keys sunset? The street carnival known as Sunset Celebration, held each evening at Mallory Square on the Key West waterfront, definitely qualifies.

Yellow and red sun setting in a red sky behind palm trees
The sun sinks behind Sunset Key

For two hours before sunset, street performers entertain the crowds with acts and physical fetes that defy description. Add arts and crafts booths, street musicians, food carts and more—illuminated by a fiery red sunset—for one funky celebration.

I start my evening with authentic Cuban dishes at El Meson de Pepe before walking over to Mallory Square. It’s hard to know where to begin. Should I watch the Great Rondini perform mind-blowing escapes or marvel at tight rope walker Will Soto?

And then there are the arts and crafts to browse. But when that big orange ball of sun begins to dip behind Sunset Key, it’s time to join the crowd, stand on my tiptoes and blindly click the camera shutter to capture the show.

Key West: Watch a sea battle in Key West Harbor

Probably the funkiest, and most fun, Florida Keys travel experience is watching the Great Bloody Battle of the Conch Republic. The pseudo sea battle is held during April’s Annual Conch Republic Independence Celebration.

Historic sailing ship in the blue water off Key West
The Jolly Roger 2 prepares to battle the Coast Guard in the Great Bloody Battle of the Conch Republic

My Key West visit coincides with the celebration commemorating the Florida Keys’ one-day succession from the U.S. on April 23, 1982, due to a federal drug blockade of the Overseas Highway. While local citizens made their point, the incident also inspired one of the Florida’s most notorious celebrations.

Like many other visitors and citizens, I’m on a boat in Key West Harbor to watch the Great Bloody Battle of the Conch Republic between Jolly Roger 2 and the U.S. Coast Guard. From the High Tide, a 33′ custom sloop, I witness the battle commence with planes dropping rolls of toilet tissue into the water while cannons from the Jolly Roger 2 shoot water at the Coast Guard boat.

sailing ships at sunset
A beautiful end to the Great Bloody Battle of the Conch Republic

The blazing sunset provides just the right mood. Of course the Conch Republic wins, which means Coast Guard officers must surrender over drinks at the Schooner Wharf Bar. Dancing to live reggae music is part of the funky fun. Yeah, mon.

Plan your trip to Key West

For more boomer travel fun in Florida, check our tips for spending a weekend on Amelia Island.

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Text on photo: Five Funky Things To Do in the Florida Keys. Photo: Sailing schooner at sunset


Disclosure: The Florida Keys and Key West provided this travel experience. However, as always, the opinions are strictly my own. 

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