Key West, the southernmost city in the contiguous United States, packs in plenty for travelers looking for warm weather and beyond. The city’s connection to the arts is evidenced by its previous residents, including Ernest Hemingway and Tennessee Williams, and can still be felt at events like its annual film festival. Opportunities for adventure focus on Key West’s sponge flats, and the colorful (not to mention delicious) marine life, while lively streets make it a fun time for those who want to stay on land.
Whether you want to go kiteboarding or get a slice of delicious key lime pie, this part of the Florida Keys is worth a stay. Ready to dive in? Read on.
Take kiteboarding lessons for a day, and you can learn how to go airborne among the waves.
Photo by Chuck Wagner/Shutterstock
1. Try your hand at kiteboarding
Kiteboarding, aka kitesurfing, involves strapping your feet to a board while a wind-harnessing kite pulls you across the water—and it isn’t for the faint of heart. Key West native Paul Menta has been at it since the late 1990s and knows the area well. One of his favorite spots is Smathers Beach, a pristine, palm-lined shore close to the airport. While Menta’s school, Key West Kiteboarding, only offers for those advanced in the sport, beginners can take lessons with other companies like Upwind Kiteboarding. Key West conditions are actually ideal for those just starting out—you can wade out for 15 miles and still be only knee-deep in the ocean.
2. Hunt for your dinner
Can’t seem to catch the wind? Maybe you’ll have better luck catching your dinner. Spearing a snapper or a lobster takes considerable skill and patience, but with the sea turtles, reef sharks, and spotted eagle rays wriggling around down there, the appealing scenery is worth the trek. Finz Dive Center, known for its spectacular nocturnal dives, offers a chartered, all-inclusive spearfishing tour that brings you out to deep-water reefs chock-full of fish.
3. Fuel up for adventure, on land
When you’re not on the water, fuel up in style. For key lime pie, head to the Reach Key West for what Afar contributor Charlene Fang calls the “prettiest key lime pie in the Florida Keys”. She describes the dish as “a vibrant, thicker-than-usual lime filling encased in an extra-buttery graham cracker crust and topped with a layer of fluffy, zest-infused sweet cream.”
In downtown Key West, you can slurp oysters or dig into fennel-infused lobster cakes at Thirsty Mermaid, which boasts the town’s only locally sourced raw bar. End your evening at Mary Ellen’s, a sports bar where you can find a (not-so-)secret takeout window serving up imaginative twists on grilled cheese. After all that paddling, you deserve it.
First-time visitors shouldn’t miss the home of one of Key West’s most celebrated residents.
Courtesy of Wolfgang Kaehler/age fotostock
4. Explore literary history at the Hemingway Home and Museum
Key West’s most famous literary resident, Ernest Hemingway, lived in a two-story Spanish-colonial villa in the island city throughout the 1920s and ’30s and composed several of his best-known works here.
His home also has the first in-ground pool in Key West, due to the insistence of his second wife, Pauline. The cost ballooned to around $20,000, a fortune in the 1930s, and was said to have contributed to the breakup of their marriage. It’s just one of the fascinating stories that guides will share on the tour of the home and gardens. And yes, you’re guaranteed to see plenty of six-toed cats, which are most likely descendants of Hemingway’s original six-toed cat, Snow White.
5. Stop by the Tennessee Williams Museum
Ernest Hemingway wasn’t the only celebrated resident in Key West. Acclaimed playwright Tennessee Williams also called this place home, living in Key West from 1941 until his death in 1983. He wrote a final draft of his most famous play, A Streetcar Named Desire, at La Concha Hotel here in 1947. Williams later bought and moved into a cottage in town. The museum, in another lovely cottage, displays movie posters, newspaper articles, photos, first editions, and memorabilia like his vintage typewriters.
Key lime pie vendors, street carts, and quirky boutiques line Duval Street, the main thoroughfare in Key West.
Photo by xbrchx/Shutterstock
6. Stroll along Duval Street
Many travelers know about New Orleans’s Bourbon Street, but Key West also has a festive thoroughfare: Duval Street. This 1.25-mile-long road runs from north to south, with the Gulf of Mexico on one end and the Atlantic Ocean on the other. It passes through the city’s historic Old Town and is lined with bars, restaurants, stores, and galleries—many of which are among Key West’s most famous, including Sloppy Joe’s, a Hemingway hangout back in the 1930s and still a hot spot today. By day it’s mostly for shoppers, but it really heats up at night, with huge crowds strolling up and down the street, live music spilling out from the bars, and a party atmosphere all around.
7. Taste quality rum at the Key West Legal Rum Distillery
It is tempting to compare distiller (and aforementioned kiteboarder) Paul Menta to Captain Jack Sparrow, including a shared love of rum and the open sea. Menta’s business dealings, however, are a bit more . . . legitimate. The Florida native opened the Key West Legal Rum Distillery, the first legal distillery in the Florida Keys, though rum has flowed through the islands for years. But this is no bathtub rum.
A chef by trade, Menta uses Florida sugarcane as his base—you can really taste it in his raw, unfiltered version—which he infuses with coconut, vanilla, and key lime to make flavored rums that are refreshingly bright (and not syrupy). Tours are fun and informative—the distillery, occupying a former saloon-turned-Coke-bottling-plant, doesn’t shy away from the shady side of the local rum trade. Visitors can examine mug shots of infamous rum-runners, watch as filtered rum is drained into the still, and taste Menta’s five spirits.
This article was originally published in 2017 and most recently updated on December 27, 2024, with current information. Jennifer Ceaser and Aislyn Greene also contributed to the reporting of this story.
