The Most Essential And Wacky Key West Experiences

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.

Duval St


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.

Key West


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.

Key West


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.

Key Lime Key West


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.

six toed cat in Key West


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.

South Beach


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.

smallest bar in Key West


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.

Margaritavilla Key West


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.

cruise ship Mallory Square


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.

Key West


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.

Key West


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.

Duval Street


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.

Duval Inn pool in Key West


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.

Casa Marina


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.

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