Five Funky Things To Do in the Florida Keys

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Is a Florida Keys road trip on your bucket list? It’s an iconic trip for boomer travelers that brings back memories of rolling down the highway with the windows open, ocean breezes, and quirky fun. If you’re headed to Florida, follow our list of funky things to do in the Florida Keys. Your itchy travel feet will thank us!


Funky things to on a Florida Keys road trip

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 found all of this and more, what I didn’t expect to find were the fun choices of funky things to do in the Florida Keys.

The bow of the African Queen heads down the canal in Key Largo.
Looking across the bow of the African Queen. Movie history, here I come.

Cruise on the African Queen in Key Largo

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:

A man kneels down on the dock to feed a tarpon that has risen above the water, mouth open ready to eat.
Feeding tarpon at Robbie’s Marina in Islamorada, Florida

Feed a Tarpon in Islamorada

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.

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 blue gin with other colorful items for sale at Robbie's Marina in Islamorada, 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:

Sign post of the Seven-mile Historic Bridge in Marathon, Florida.
It’s a beautiful day for walking the Seven-Mile Historic Bridge

Walk With Florida Keys History on the Seven-Mile Historic Bridge

A Florida Keys road trip on the Overseas Highway is meant for taking it slow and enjoying the scenery. In Marathon, 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.

The old highway of the Seven-mile Historic Bridge stretches into the distance with a cloud-filled sky overhead.
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:

An orange sun sinks behind the palm trees of Sunset Key in Key West, Florida.
The sun sinks behind Sunset Key

Sunset Celebration at Mallory Square in Key West

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.

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.

The Jolly Roger 2 prepares to battle the Coast Guard in the Great Bloody Battle of the Conch Republic.
The Jolly Roger 2 prepares to battle the Coast Guard in the Great Bloody Battle of the Conch Republic

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.

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.

A sunset colors the sky as silhouettes of sailing ships cruise on the water in Key West.
Key West Harbor is the place to be during the Great Bloody Battle for the Conch Republic.

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.

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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