Key West is more than a little weird…but in a good way. I mean, in 1982 they seceded from the US (for all of 5 minutes) as they protested a border checkpoint. The primary military aggression involved hitting an actor in a naval uniform over the head with a stale loaf of Cuban bread. They call themselves “Conchs”, which is the slug of the sea and best served deep fried. Not to mention there are loose chickens running around everywhere!
Little wonder then, that you’ll find it easy stumble off the tourist track and seek out some truly offbeat and unique things to do in Key West.
We are all about weird here at Wayfaring Views (the phallus museum in Reykjavik and the sewer museum in Paris come to mind). We’ve been to Key west and done some weird stuff there. But it’s been a minute since we visited, so we tapped into some of our travel blogger friends to offer up some options.
I also reached out to local resident Pony. Yes, that’s his real name. He and I met on the Camino de Santiago and we bonded while singing bawdy show tunes on the pilgrimage trail. Pony is a hairdresser, Disney fanatic, comedian and long time Key West resident.
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Where to Stay in Key West
Key West has a wide range of accommodation, from traditional beach resorts, to historic B&Bs to a floating condo. So, you can literally float your boat while booking accommodation in Key West.
But, book early. Key West is a popular tourist destination and lodging isn’t cheap. The earlier you book, the better your deal. And if your travel plans are at all uncertain, look for refundable room deals.
Look at the Southernmost Point Guesthouse for a really nice hotel that is conveniently located…but away from the noisy bar spots. The Hyatt Residence Windward Point has ocean view AND kitchenettes. And the Knowles B&B is a nice budget choice (by Key West standards) with a cozy vibe, pool and breakfast included.
Why Try These Unique Things to do in Key West?
Sure, go to Mallory Square for sunset and have some adult beverages on Duval Street and take your picture at that “southernmost point” sign (but please don’t forget and Hawaii and all of the US territories are actually further south).
But you can do those things and still make time for an off the beaten path Key West vacation, because the island is small, clocking in at 7.2 square miles. You can walk from the northeast corner to the southwest corner in an hour and a half.
The island delights in being quirky, so you should lean into that culture, make like a Conch and dig into hidden Key West
Off the Beaten Path Key West Attractions
What follows are our 13 suggestions for how to get off Duval and into the quirky side of the Keys.
1. Key West Cemetery
One of the more creepy and unusual things to do in Key West involves a visit to the city cemetery. It was founded in 1847 following a hurricane that destroyed the previous graveyard. To prevent future flooding, they relocated it to Solares Hill. So, you can visit the gravesites and get a bit of a view at the same time.
There are some very quirky gravestones in Key West, with the dearly departed proclaiming things like “devoted fan of singer Julio Iglesias”, Admiral, Conch Republic Navy” and “I’m just resting my eyes”.
It’s best to pair the cemetery visit with a bike rental. This allows you to explore the cemetery, but also do a circuit of the whole island. There are bike rental shops all over Key West, so you can simply pick one that’s close to your lodging. Or you go to Island Bicycle, which is just east of the cemetery.
Read More: If you are keen on cemeteries, then you should also visit offbeat New Orleans and the Pere Lachaise cemetery in Paris.
2. Blue Heaven Rooster Cemetery
(Suggested by Lori from Travlinmad)
If you’re searching for the kind of Key West that Jimmy Buffett sings about, with “a flashback kind of crowd”, you’ll find it at the inimitable Blue Heaven, one of the coolest and quirkiest places in the Conch Republic.
It’s located on Petronia Street, which was once a makeshift neighborhood boxing ring. The likes of Ernest Hemingway himself spent many a night here fighting in the ring.
Today, the Blue Heaven is a Key West treasure known for its amazing food, daily live music and garden setting under the tree canopy.
It wasn’t long ago that chickens roamed freely under the tables, pecking near your feet as you enjoyed your dinner as they foraged for theirs. But they’ve since passed on. In the corner near the event stage you’ll find the graves of many of these famous layers and cocks, who have sadly crossed the poultry rainbow bridge. Be sure and check out the epitaphs — they’re almost as good as those in the Key West Cemetery!
Be sure and come to Blue Heaven for breakfast (their Eggs Benedict is renowned) or dinner, and don’t miss a slice of their mile-high Key Lime Pie.
3. Mel Fisher Maritime Heritage Museum
Fisher was a lifelong diver and treasure hunter whose 17 year quest finally hit pay dirt in 1985. His salvage crew recovered $450 million in buried treasure just offshore of the Key West coastline.
The bounty came from the Nuestra Señora de Atocha galleon, which sank during a hurricane in 1622.
You can see a lot of the goods on display at the Mel Fisher Maritime Museum. They have gold bars, chalices and jewelry along with exhibits on the Caribbean slave trade. They are actively involved in conservation work as well.
The museum is a fun Key West attraction for history buffs, treasure hunters and would-be pirates.
4. Key West Wildlife Center
The mission of this nonprofit organization is to ensure the future of Key West’s diverse native wildlife through rescues, rehabilitation and (hopefully) releases.
They are particularly active with wild birds, like brown pelicans. But they also have an arrangement to do rescue and rehab for Key West’s crazy crew of feral chickens. The Center also works with sea turtles, tortoises and marine mammals.
They offer public education programs which include a nature trail, freshwater pond, two aviaries and some locations for observing the wild bird migrations.
This is not a zoo, but it does offer a cool opportunity to see the local wildlife. The Wildlife Center is definitely an off the beaten path Key West experience people usually find it on recommendation of a local.
The Wildlife center is free, but if you visit, please give them a donation.
5. Key West Martello Tower
The Key West Martello Tower is where the Civil War meets the ladies who lunch.
The tower is a relic of the unusual political position that Key West took during the civil war. It was the only southern city that allied with the Federal government. The east and west Martello batteries were constructed in 1863 to provide support for nearby Fort Zach.
Perhaps the laid back Key West vibe was at work, because it took so long to build the towers, that they were never actually put into service for the war. After cycling through several uses, the West Tower has now become part of the Key West Garden Club. So, you can literally find a hidden Key West history lurking amidst the orchids, roses and tropical bromeliads.
6. Books & Books
For a book nerd like me, there is nothing better than killing an hour or two in a local indy bookstore. If you like to do the same, you should check out Books & Books. This small indy chain started in Naples, Florida and they came to Key West in the mid oughts. If you are lucky, you may even be able to hang out with Judy Blume, because she is a co-founder of the store and she occasionally works there.
Key West is a literary city and Books & Books carries on that tradition by curating staff pics and featuring local authors. The store is part of The Studios @ Key West, with is a nonprofit organization on a mission to provide low cost studio space for local artists and performers.
Read More: For more literary love, check out our article on the most beautiful libraries in the world…it will blow your bucket list out of the water!
Fun Activities to do in Key West
7. The Dry Tortugas
The Dry Tortugas isn’t exactly an off the beaten path Key West activity. People know about it and tourists do take the boat trips out there. But it’s worth mentioning because it is one of the strangest, loneliest and loveliest national parks in the US.
Construction was started on the fort in 1846 and thirty years later it still wasn’t quite finished. The original intention was to provide an advanced post for ships patrolling the Gulf of Mexico and the Straits of Florida. The fort never fulfilled its military mission, but the port was used as a refueling station and prison (most notably housing John Wilkes Booth’s physician).
It’s worth carving out time to do the day trip out to the island. You can take a history tour of the fort and then snorkel around it’s edges. Book ahead for the catamaran tour.
8. Danger Charters
Danger Charter is one of the local outfits recommended by Pony. They rate the rare full five stars from Trip Advisor. Their boats are 65-foot schooners designed to replicate the classic skipjacks used by the wreckers and fishers who worked the Keys in the 19th century.
Their more modern activities include sunset cruises, snorkel and kayak trips. What’s cool about Danger Charters is that they go into the Key West National Wildife Refuge, so you can experience both open water and the mangroves. This isn’t a booze cruise, but rather an on-the-water adventure for people who love nature.
9. Comedy Key West
Comedy Key West is the only comedy club on the island. In addition to the usual headliners, and locals like Pony, the club also offers some unusual comedy experiences. You can try their “paint ‘n’ chug” (because they think that sipping is for wussies). This offbeat Key West activity involves comedy, drinking and wet paint. Because of course.
If you think that you are hilarious, they also host an open mic night on Tuesdays. And don’t miss the drunk spelling bee at Mary Ellen’s Bar, because libations and hard to spell words are a recipe for the perfect spit take.
10. Lazy Dog Kayak & Paddle
The owner of Lazy Dog has the right idea. Just when she was at the top of her game in a white collar profession, she chucked it all to become a Conch, writing about her transition in the book, Millionaire in Flip Flops.
Her company offers a variety of kayak and SUP tours, including DIY tours, guided eco tours and getting into the backcountry.
Unique Places to Eat (and Drink) in Key West
11. Retro Room (or Glitchcraft Cafe & Gameroom)
They call themselves the Retro Room, but the locals call them the Glitchcraft Cafe & Gameroom. They are pretty off the radar and don’t have much of an internet presence. That makes them an altogether better place for hiding out from some of the tourist crowds in Key West.
They offer a chill atmosphere and 24 beers on tap. They also have trivia nights, board games and action figures.
12. Brothers Grocery
5 Brothers is an old school place that’s popular with the locals. They specialize in Cuban food with a great cafe con leche and Cuban sandwiches. Their burgers and huge empanadas are delish too.
Key West can be a very expensive place to eat, but 5 Brothers offers generous portions, for a great price.
13. Funky Rooster Coffee House & Wine Bar
The Funky Rooster has a lot going on. They are a coffee house, a wine bar and a store featuring locally made art and clothing. The Funky Rooster is a social place and they very deliberately don’t have public wifi.
Try one of the tasty pastries or their kinda famous smoothies. Or grab a glass of wine and sit on the porch, watching the world go by.
Explore more of Florida and enjoy some outdoor adventures in Panama City Beach.
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Sunday 1st of August 2021
The author's name is Judy Blume, not Bloom. That's an easy spelling to check. Also, the plural of local is locals, not local's. Apostrophes don't make words plural.
Wednesday 5th of January 2022
@Judy Blume, Love you and your books always! I'm 53. First time in Key West this week, staying on a catamaran. Love the vibe!
Thursday 16th of December 2021
@Motherducker, Don’t be a pompous ass.
Saturday 24th of July 2021
Go to two friends restaurants on front st
Sunday 5th of September 2021
Awesome place...owned by my parents old classmates!!! I miss commodores. I love KW and miss it. Its Def not weird. Well ID use the word fun and laid back. Now Robert The doll weird, and the man who wouldn't bury his wife are odd lol.
Sunday 5th of September 2021
Saturday 12th of June 2021
John Wilkes Booth never went to ANY prison, much less Fort Jefferson in the Dry Tortugas. The person you're thinking of is Dr. Samuel Mudd, the doctor who set Booth's leg after he shot President Lincoln. Mudd was released early from his life sentence after his life-saving efforts during a yellow fever outbreak on the island.
Saturday 27th of November 2021
@Mick Dahlstrom, they said Booth's doctor at the beginning.