The most southern point in the continental U.S., Key West has been memorialized in music and literature for nearly 100 years now — Ernest Hemingway called this island home for a while, and Jimmy Buffet loves to sing about its laid back boozy attitude. Plus it’s actually closer to Havana, Cuba (90 miles) than it is to Miami (more than 100). Here are 15 essential and wacky Key West experiences.
1. Duval Street bar crawl
Key West is a hard drinking town, and most of its bars are crowded along Duval Street. Spend a night hopping between them. Sloppy Joe’s and Willie G’s are two of the most famous.
2. Snap a picture at the southernmost tip
There’s a giant buoy marking the spot, and usually a line of tourists stretching for half a block to snap a picture in front of it.
3. Look for the fish truck
Key West is known for its zaney characters and kitschy art, and this truck is the epitomy of all things Key West. It’s usually parked on one of the main streets in town.
4. Eat Key Lime
In Key West they are crazy about Key Lime anything, and they’re also pretty nuts about cigars, so it makes sense at some point someone would create a key lime flavored cigar.
5. Six toed cats
Ernest Hemingway lived in Key West from 1931 to 1939 and today you can visit his former home, which is preserved as the Ernest Hemingway Home & Museum. The descendants of his famous six-toed cats still live on the premises.
6. South Beach
Despite the gorgeous turquoise water, Key West isn’t really a beach destination with only a handful of spots to chill on the sand. In town, South Beach (pictured above) is one of the most popular and you can rent beach chairs. Tennessee Williams used to swim here daily.
7. Have a drink at the town’s smallest bar
It’s name is simply “Smallest Bar” and this tiny spot on Duval Street has the distinction of being the “smallest bar in Key West.” Grab a drink just to say you did so.
8. Have a margarita in the original Margaritaville
Today there are Jimmy Buffet Margaritaville franchises all over the world, but the original outpost is in Key West. Pop on in for a drink.
9. Mallory Square sunset
Head to Mallory Square for a nightly sunset celebration as the sun sinks over the Atlantic Ocean. This is also where the cruise ships dock.
10. Eat fresh seafood
From conch fritters to lobster rolls, seafood pasta to blackened snapper sandwiches, Key West is choke full of good seafood options. Don’t skip out.
11. Destination selfie
Take a selfie in front of this sign on the promenade by Mallory Square. It’s way cooler than the southernmost tip sign, especially if you’ve traveled to any of these places.
12. Get in the water
Whether you take a snorkeling trip to a nearby reef or go for a sunset sail, it is imperative to get out on the water in Key West. Jet ski tours are also popular.
13. Shop Duval Street
Duval Street is known for its drinking scene, but stroll it by day to do some shopping — there’s everything from the requisite bawdry t-shirt shops to more classy boutiques.
14. Sleep boutique
Key West is choke full of quaint little guesthouses, many with private pools like the one at the Duval Inn featured here. Note prices during the season can be super expensive for the size of the rooms, however.
15. Sleep classy
The classiest place to stay in town is Casa Marina, which is a Waldorf Astoria resort and has the best beach in town. The design is cool as well.