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Key West may be small (it’s only 4 miles long), but it’s packed with things to do. Being the final stop on the Overseas Highway and the southernmost populated area in the U.S., It’s like all the eccentricity and revelry in the country slowly sank down to combine with the vibrant culture of the Caribbean to make a ridiculously fun haven for artists and vacationers alike.
Whether you’re looking for tropical outdoorsy adventures, mouthwatering cuisine or laughably weird historic sites, Key West has you covered. You can hit all the high points in a weekend, but if you really want to dive into the culture of this unique island, it’s better to give yourself closer to a week.
Pro Tip: Save up to 50% on Key West’s top attractions with the Sightseeing Pass.
When to Visit Key West
Key west can get pretty hot and steamy during summer, although the heat is somewhat tempered by the ever-blowing sea breeze. Temperatures often reach the low 90s, so summer visits are best for sun worshipers or those planning to spend most of their time in the air-conditioning.
Winter is high season in Key West, so be sure to book accommodations well in advance if you’re visiting then. Due to the small size of the island, there’s a limited number of hotels and campgrounds.
The ideal time to visit Key West is spring. Winter crowds have died down while the temperatures remain in the 70s and 80s. Hurricane season doesn’t start until June, so it’s unlikely that you’ll have to cancel your travel plans due to Mother Nature.
Explore Key West
Old Town, the heart of Key West, can easily be explored by foot. But if you get tired of hoofing it, hop on the Duval Loop, a free bus that loops around Old Town every 30 minutes.
1. Duval Street – Key West’s main drag is what you’d get if New Orleans and Nassau had a baby. It’s rowdy (in a good way) and crowded, with countless bars and restaurants spewing live music and drunken tourists out into the streets well into the wee hours of the morning. There’s plenty of souvenir shops as well as large chain stores like Banana Republic and Coach. All of it set against a beautiful Caribbean backdrop.
2. Mallory Square – Key West has been holding Sunset Celebrations at Mallory Square since the 1960s. The festivities begin two hours before sunset, when the square comes alive with street performers, artists, musicians and more.
3. Southernmost Point Buoy – Located at the southern (duh) end of Whitehead Street, it’s a great photo op. But be aware that EVERYTHING ABOUT THIS BUOY IS A LIE.
It says it’s 90 miles from Cuba, but it’s actually 94 miles away. And it’s not even the Southernmost point in the continental U.S.! That’s actually a spot on the restricted-access Navy site just a few hundred yards away from the buoy.
But that’s not even true! The real, legit southernmost point in the continental U.S. is a private island called Ballast Key, 10 miles away from the buoy. What other lies are you telling us, buoy?!? (What a weird word. Buoy buoy buoy.)
4. Key West Historic Seaport – Lots of trendy shops and restaurants, plus a working marina where you can watch the ships come in. You’ll see everything from small fisherman’s boats to multi-million dollar yachts.
5. Mile Marker 0 – The dawn of all creation, the genesis of the world! Or maybe just the beginning of U.S. Highway 1 AKA the Overseas Highway. Either way, it’s a fun spot to take one of those cheesy pictures of yourself standing in front of a random landmark.
6. Skydive Key West – What better way to explore the area than with a bird’s eye view? I would likely end up peeing my pants, tiny pee droplets raining down over the islands as I shriek in terror. But you might enjoy the feeling of flying in one of the top skydiving locations in the world.
Key West Arts & Culture
7. Key West Mural at Cuban Coffee Queen – A famous mural painted by local artist Letty Nowak decorates the side of this coffee shop. The perfect spot for an Instagram portrait.
8. Florida’s Living Reef Mural – One of the largest murals on the island, it’s a massive depiction of undersea life located near the corner of Caroline and William Streets. It was painted by one-name artist Wyland, who probably belongs to a secret club with other one-name artists like Cher and Madonna.
9. Bahama Village Mural – Located in the Bahama Village neighborhood at the corner of Petronia and Thomas Streets, this mural illustrates everyday life in a colorful Bahama town. It was painted by Rick Worth, a local artist who has been instrumental in growing Key West’s public art offerings.
10. Roaming Chickens – Why is this in the arts & culture section? Because feral chickens have been part of Key West’s culture since before you were born. Settlers brought chickens to the island back in the 1800s, and their great-great-great grandbaby chickens have since flourished due to the mild weather and lack of predators. You can’t walk more than a few blocks in Old Town without seeing a hen or hearing a rooster crow.
11. Seward Johnson Sculptures – Check out the 20-foot tall “Time for Fun” sculpture in front of the Custom House, depicting Renoir’s twirling dancers. Then stop by the Tropic Cinema to see Johnson’s statue depicting the famous Marilyn Monroe dress scene from The Seven Year Itch.
12. Key West Sculpture Garden – Right in Mallory Square you’ll find 39 bronze busts depicting historic Key West folks like Ernest Hemmingway, Henry Flagler and Harry Truman.
13. The Studios of Key West – Lots of local art in the gallery, plus classes, plays and other events. A unique cultural center and a great spot to get some one-of-a-kind art.
14. 7 Artists & Friends – An eclectic little gallery just a couple of blocks from the hustle and bustle of Duval Street. It’s filled with local art, and the owner, Jennifer, and her pup, Mr. Fancy Pants Uncle Tooche Jones, are friendly and welcoming.
15. Reality is a Drag Show – One of the funniest, most entertaining shows in town, held every single night at Aqua. Audience participation is part of the show, so sit in the back if you’re shy. Expect singing, dancing and strong drinks.
Key West Nature & Wildlife
16. Audubon House and Tropical Gardens – The incredible gardens contain hundreds of tropical plants, including over 200 orchids and a medicinal herb garden. The house contains dozens of detailed bird illustrations created by famous ornithologist John James Audubon.
17. Nancy Forrester’s Secret Garden – Nancy Forrester has been rescuing parrots for 30 years. She created this haven so that guests can interact with her birds, who have big personalities. Ara Ara has a foot fetish – she loves toe rings, ankle bracelets and shoes that light up when you walk. Mr. Peaches loves cell phones and tablets. He’s also a big fan of Facetime.
18. Dry Tortugas National Park – About 70 miles off the tip of Key West, lies a legit fairy tale realm. Seriously, Dry Tortugas is an old fort that looks like a friggin’ castle soaring over impossibly turquoise waters that stretch out as far as the eye can see. It’s like a deserted island, except you’re surrounded by other tourists.
Tour the massive 19th-century castle fort and take a stroll along the ramparts while pretending you’re a princess surveying her future queendom. You’ll also want to survey the underwater part of your queendom, since it’s one of the top snorkeling and scuba diving locations in the world. The coral reef is brimming with tropical fish, anemones, sea turtles, rays and bigger creatures like dolphins, barracudas and sharks.
And get this, you can actually spend the night in this otherworldly realm. It’s primitive camping with zero amenities, so there’s no concierge or room service – it’s more composting toilets and no cell phone coverage. But it’s incredible feeling like you’re at the edge of the world, listening to waves lapping at the island, feeling the warm tropical breezes and sleeping under a sky brimming with stars.
To get there, catch a ride on the Yankee Freedom ferry or if you feeling fancy, charter a seaplane.
19. Bayview Park – Right in between Old Town and New Town, this family-friendly park has a sweet picnic area, a playground, tennis and basketball courts, and a cool little pavilion. They often hold festivals and events at the park, so be sure to check their calendar before you go.
20. Key West Butterfly and Nature Conservatory – You like butterflies? If yes, this is a must. (If no, what kind of monster are you?) It’s less crowded in the morning and the butterflies are more active. The gardens and butterflies (over 50 different species) are all housed in a climate-controlled greenhouse. You’ll also see turtles, flamingos and other birds chillin’ in the gardens.
21. Key West Garden Club – If you need a break from the rowdy streets of Key West, go enjoy the peace and quiet at this historic fort turned tranquil garden. This place is seriously gorgeous. The brick pathways wind through lovely little courtyards, with tons of colorful flowers and trees, all overlooking the Atlantic. Be sure to check out the butterfly garden.
Key West Beaches
Key West is not known for its beaches. You won’t find any of those picture-perfect, powder-sand tropical beaches here. Nope, it’s mostly small beaches with rough sand (or rocks), muddy seabeds and lots of seaweed.
But it’s not bad if you’re just looking for a nice spot to lay out and enjoy the sun. And if you swim out past the seaweed, the water is like a warm, crystal clear elixir of youth filled with colorful fish and marine life.
22. Boca Chica Beach – Just a few miles from Key West, off a washed out road and through a fence decorated with random shoes (“lost soles”), you’ll find Boca Chica Beach. This is the Florida Keys’ only legal nude beach. Down the path you’ll find the Lonely Night Saloon, an impressive lean-to made out of driftwood. Feel free to tan your naughty bits here, but be sure to leave by midnight or risk getting kicked out by the popo.
23. Fort Zachary Taylor State Park – You can tour the historic fort and walk along the nature trails in the park, but the real draw here is the beach. It’s hands-down the best beach in Key West. The shore and sea floor are a bit rocky, but the waters are clear and excellent for swimming or snorkeling. Rent snorkel gear at the park, grab a bite to eat at their cafe and stick around to enjoy those famous Key West sunsets from one of the many picnic tables throughout the park.
24. Higgs Beach – A moderately sized beach with a nice sandy area for laying out. Not good for swimming though, as the sea bottom is muddy. Be sure to check out the pier and African slave cemetery.
25. Simonton Street Beach – Small, dog-friendly beach with chair rentals, a boat ramp and public restrooms. It’s on the edge of Old Town, but not as touristy as other Key West beaches.
26. Smathers Beach – Large (for Key West), sandy beach with public restrooms, showers, volleyball courts and jet ski rentals. Lots of seaweed in the water, but if you go out a ways it clears up.
27. South Beach – Near the Southernmost Point Liar Buoy, South Beach is small but popular. Softer sand than some of the other beaches and shallow waters make it a nice spot for families, although you will find some seaweed as with most of Key West’s beaches.
Key West Historic Sites
28. Hemingway House – Built in 1851 and bought by Hemingway in 1931, the Hemingway House is known for having a ridiculously expensive pool and a bunch of six-toed cats.
Hemingway’s second wife, Pauline, had the pool built while he was in Spain working as a war correspondent. She spent a staggering $20,000 (over $300,000 in today’s dollars) to have the massive hole dug out of solid coral, then filled with ocean water (there was no fresh water available in Key West at the time) via a pump that took up to three days to fill the pool, which had to be drained and cleaned every few days due to algae and debris build up.
When Hemingway got back from Spain (prepared to dump his wife for the new hottie he shacked up with in Spain) and discovered how much Pauline had spent, he threw a penny onto the ground and shouted, “You’ve spent all but my last penny, so you might as well have that!” The penny is embedded into the concrete at one end of the pool to memorialize the fun occasion.
As far as the six-toed cats go (I see all you crazy cat ladies clapping your hands and squeeing), there’s roughly 50 of them living on the property, all descendants of Hemingway’s six-toed cat, Snow White. The museum cares for the cats, but they’re always in need of volunteers to provide ear scritches and belly rubs to the little monsters.
29. The Custom House – The headquarters for the Key West Art & Historical Society, The Custom House holds exhibits on local history, famous Key West personalities and local art. Lots of different collections make it an interesting place to spend a couple of hours.
30. Bahama Village – A sub-section of Old Town, this was originally where the Bahamian workers (basically slaves) lived. Many of their 19th-century homes still stand along the narrow streets. It’s now been thoroughly gentrified, with lots of cute little shops and restaurants as well as Key West’s public swimming pool. But you can still see the original cobblestone streets and colorful Conch architecture.
31. Lighthouse Tower – Key West’s historic lighthouse opened in 1848 with one of the first female keepers in the country, who cared for the previous lighthouse as well and weathered at least five hurricanes. Grrrrl power! The lighthouse and keeper’s quarters showcase the maritime history of Key West and the lighthouse keepers. The view from the top of the lighthouse is breathtaking.
32. Fort East Martello – History, war relics, culture, blah blah blah. The real reason to visit Fort East Martello is to see the Ghosts of East Martello exhibition. They’ve got Robert the Doll, you guys. ROBERT THE DOLL! Never heard of him? Take a seat cuz this shit is crazy.
Way back in 1904, this kid named Robert was given a life-size doll, which he named after himself because kids are tiny narcissists. Supposedly the doll would terrify the kid by destroying his room, and people reported hearing the doll giggling in a creepy Chucky-like manner.
Robert the Doll now lives at this museum, and he curses people who take his picture without first asking permission. The walls surrounding his glass case are literally plastered with letters from visitors begging his forgiveness and asking him to remove the curse. He’s been blamed for everything from divorces to car accidents.
If terrifying dolls aren’t your thing, how about medical experiments, grave robbing and corpse marriage? The museum covers the story of a crazy German x-ray tech named Carl, who called himself Count von Cosel. He was working at a Key West hospital when a beautiful young woman named Elena was brought in with tuberculosis.
Carl fell madly in love with Elena and set about curing her with his experimental “electrical therapy.” Obviously that didn’t work and she died. Well Carl lost his damn mind and stole her body from the cemetery. He “restored” her body over the course of two years, all while guided by her spirit’s voice. His nutso behavior eventually led the cops to his home, where they found Elena’s Frankenstein body dressed in a wedding gown.
So what did the cops do? You guys. They put her body on display, then dismembered it and buried the pieces in an undisclosed location. What?! Oh, and Carl was left free to go about his business as a certified psycho. Only in Key West!
33. Mel Fisher Maritime Museum – Mel Fisher was a chicken farmer turned treasure hunter, who basically became the Indiana Jones of the sea. He discovered multiple shipwrecks over the years, most famously a Spanish galleon off the coast of Florida with $450 million in gold, silver and emeralds. The state of Florida declared ownership of the cache, but Fisher was like, “Nuh uh.” They took the case to the Supreme Court, who basically said, “Finders keepers.” Fisher got to keep 75% of the treasure, making him rich AF. Now he has a museum in his name, where you can view shipwreck artifacts and learn about conservation methods.
34. Blue Heaven Rooster Cemetery – A small, historic graveyard for some of the most important poultry to ever roam the island. Located in the courtyard of the eclectic Blue Heaven restaurant.
35. Harry S. Truman Little White House – While the rest of us enjoy minimal to no vacation time each year, presidents sometimes go off for months at a time. I guess they might get some work done while on holiday (gotta love those urgent emails from coworkers who KNOW you’re on vacation), but I’m pretty sure presidents are just for show and there’s actually a shadowy network of uber-wealthy industry titans who get things done. I’m not paranoid, you’re paranoid! Anyway, President Truman was an old school snow bird, spending his winters in Key West at the “Little White House.” The building is now a museum where you can tour the living quarters and view some of Truman’s belongings, including his famous “The Buck Stops Here” sign.
36. Key West Cemetery – Just like the people of Key West, the cemetery is a bit odd and full of interesting stories. Grab a tour guide from the office and explore the 19 acres of tombs and headstones, many of which have quirky or funny sayings inscribed. A couple to note: Edwina Larez – “Devoted Fan of Singer Julio Iglesias” and B. P. Roberts – “I told you I was sick.” Watch out for the wild iguanas.
Key West Food & Drink
37. Sip Some Coffee – Keys Coffee Co. and Cuban Coffee Queen make the best coffee on the island. Both have good smoothies and breakfast food, too.
38. Devour Breakfast – Pepe’s, founded in 1909, is the oldest restaurant still operating in Key West today. Their breakfast is home cooked perfection. Banana Cafe is another great choice, serving up waffles, omelets and crepes that are to die for. Weird fact: their logo has what appears to be a one-breasted woman wearing a skirt made out of bananas. How could you pass that up?
39. Grab Lunch – What started out as a makeshift food truck is now B.O.’s Fish Wagon, a funky driftwood shack serving the best fish sandwich on the island. For inventive burgers, tacos and burritos, try Garbo’s Grill, an Airstream trailer turned restaurant run by a couple who go buy the names Princess Buttercup and Grande Cabeza.
40. Sit Down for Dinner – If you’re feeling fancy, take the ferry (which runs every 30 minutes) from the Westin to Latitudes on Sunset Key. They’ve got award winning food and great views, but there is a dress code, so no scrubs allowed. For something more low-key, head to Bliss, where you’ll find delicious Latin fusion dishes and excellent sangria. Also check out the authentic Cuban cuisine at El Siboney.
41. Wash it Down with Drinks – Key West is known for its watering holes, so it’s kinda hard to narrow it down to just a few. But you can’t go wrong with Sloppy Joe’s, a Key West landmark and an old Hemingway favorite.
Captain Tony’s is another institution, housed in Key West’s original morgue. Check out the tree growing through the middle of the bar. It was originally a “hanging tree” where 17 people were hanged. The bar is a celebrity favorite, with everyone from Jimmy Buffett to JFK visiting.
If you want something a little less macabre, head to Sunset Pier at the Ocean Key Resort. It’s a trendy oceanfront restaurant and bar with some of the best sunset views in Key West.
42. Gorge on Dessert – If you don’t eat a slice of key lime pie at Kermit’s, the locals are likely to burn you at the stake. Not really, but Kermit’s really does have the best key lime pie. It’s actually been featured on the Food Network and National Geographic. For other options, like “Man Flowers” and “Cookie Nookie Pie,” head to Better Than Sex. Yes, yes it is.
If you need a place to stay after all the excitement, check out the 6 best resorts in Key West.