Sure, you’ve probably strolled down Duval Street, sipped a Key lime margarita, and taken a selfie with the Southernmost Point Buoy. But this quirky corner of the Florida Keys has a whole other side—full of the wild, the weird, and the downright wonderful. From ghost tours to food and cocktail adventures, these are the best places and most unique things to do if you’re ready to shake up your next trip.
Pack your sunscreen, your curiosity, and maybe a flamingo-themed fanny pack—because we’re diving into the offbeat side of the southernmost city in the continental United States.
1. Take a Wacky Bike Tour with Lloyd
If Willy Wonka ran a bike tour, this would be it. Lloyd’s Tropical Bike Tour is part ride, part comedy act, and part guided tour of Old Town Key West’s hidden tropical gardens. You’ll meet chickens, taste fresh fruit (cracked open with a machete, of course), and possibly hear Lloyd play a conch shell like a trumpet. This guy is a local legend and a national treasure.
- Where: 601 Truman Ave.
- Cost: Around $50
- Fun Fact: He was featured in The New York Times and still has a perfect 5-star rating. Respect.
2. Flamingle with Rhett and Scarlett
The Key West Butterfly & Nature Conservatory isn’t just about fluttery wings. You’ll also meet Rhett and Scarlett, two flamingos with major diva energy. Stroll through tropical gardens, chat with exotic birds, and book a Flamingle Encounter for an unforgettable photo op.
- Where: 1316 Duval Street
- Cost: ~$15 general admission, extra for Flamingle Encounter
- Pro Tip: This spot is air-conditioned and open daily. Perfect for a mid-day cool down.
3. Take a Ghost Tour (and Meet Robert the Doll)
Sure, ghost tours are fun—and in Key West, you’ve got options. Take a spooky walking tour through Old Town, hop aboard a haunted trolley, or visit the infamous Robert the Doll at East Martello Museum. Learn chilling stories about the Key West Cemetery, Captain Tony’s Saloon, and other haunted historic sites.
- Where: Various locations across Old Town
- Cost: ~$25–$40 depending on the tour
- Fun Fact: Robert the Doll is so creepy. Be sure to ask permission before snapping a pic!
4. History and Ocean Views at Fort Zachary Taylor
While the park closes at dusk, Fort Zachary Taylor is still worth a visit during the day. Explore Civil War history, stroll the shady trails, and enjoy one of the best beaches in Key West. Pack a picnic and snorkel gear to make a full day of it.
- Where: 601 Howard England Way
- Cost: Around $6 per vehicle
- History Buff Note: Fort Zach played a role in both the Civil War and the Spanish-American War.
5. Eat, Drink, and Be Key West-y
Take a guided walking tour with Key West Food Tours where you’ll sip tropical cocktails, taste local favorites like conch fritters and Cuban coffee, and—of course—enjoy a slice of that legendary Key lime pie. Whether you’re a foodie, a cocktail connoisseur, or just really hungry, this experience is one of the best ways to dive into the flavors of the island.
- Where: Tours start near Duval Street
- Cost: ~$85–$90
- Pro Tip: Come hungry and wear your stretchy shorts.
6. Kayak Through Bioluminescence
Glide through shallow waters near Stock Island after dark and watch the Atlantic Ocean glow beneath your kayak. Dinoflagellates (glow bugs of the sea) light up with every paddle stroke. Nature is amazing.
- Where: Tours launch from Stock Island
- Cost: ~$85 per person
- Pro Tip: The best time for this is during the summer months when the water is warm and the moonlight is low.
7. Treasure Awaits at the Mel Fisher Maritime Museum
Channel your inner pirate and hold a real gold bar from the shipwrecked Spanish galleon Atocha. This national historic landmark is filled with artifacts, tales of slave ships, and the obsession of one man who spent 16 years searching the sea floor.
- Where: 200 Greene St.
- Cost: ~$17
- Cool Bonus: Learn how underwater archaeologists work and see real Spanish coins.
8. Garden in a Fort
Inside the West Martello Tower, a Civil War relic turned tropical wonderland, you’ll find the Key West Garden Club. It’s one of the best hidden gems on the island—complete with palm trees, orchids, and ocean views from Higgs Beach.
- Where: 1100 Atlantic Blvd
- Cost: Free (donations welcome)
- Fun Fact: This is also one of the most popular wedding venues in Key West. Because nothing says romance like cannons and hibiscus.
9. Sunset Sandbar Party
Mallory Square is great, but the best sunset cruise might be your own private boat ride to a sandbar. With a cooler full of drinks, some good tunes, and your toes in crystal clear waters, it’s paradise without the crowds.
- Where: Depart from Key West Marina
- Cost: Starts at ~$99 per person
- Pro Tip: Book during off-peak or shoulder season to avoid hurricane season chaos.
10. Hop on a Tiki Bar Tour with Up The Keys
Want to hit the best tropical watering holes without worrying about driving? The Tiki Bar Tour from Up The Keys takes you on a breezy ride to some of the island’s most fun and flavorful bars. You’ll visit hidden gems, sip signature cocktails, and enjoy the good vibes that only the Florida Keys can serve up.
- Where: Tour departs from Old Town Key West
- Cost: Check UpTheKeys.com for latest pricing
- Pro Tip: Bring your party spirit and maybe a feathered lei. Because why not?
So… What Will You Try First?
Key West isn’t just a place—it’s a state of mind. Whether it’s sipping rum, paddling through glowing waters, or swapping stories with six-toed cats at the Hemingway House, there are always new favorite things to discover on this tiny island.
Want more adventures, tips, and fun facts? Stick around. We’ve got a whole conch tour train of weird and wonderful to explore together.
