You Can Explore This Coastal Florida City Entirely on Foot—and It’s Stunning

Florida is a wonderful state, but it's not a very walkable one. As in most of the U.S., many of the state's cities were developed after cars were invented so they were built around motor transportation rather than walkability. Thankfully, Florida has Key West, a small laidback island at the tip of the peninsula that's blissfully free from the constraints of car-obsessed American culture and nestled cooly by the sea. It's common for people here to walk or bike around and spend time outdoors rather than hiding from the sun. Because of its size and great urban planning, quirky Key West might just be the most walkable city in all of Florida. 

Why Key West Is So Easy to Explore on Foot

The southernmost city in the continental U.S., Key West is merely two miles by four miles. Some people might get claustrophobic at the idea of being in a place so small, but I find the island’s size the main reason for its charming personality. It allows for the existence of a true community made up of neighbors who know each other’s names and locals who welcome tourists with open arms. Compactness is also what makes Key West, one of the most scenic cities in Florida, walkable. Many, if not most, streets have sidewalks and bike lanes (I know, shocking!), encouraging people to move around without a car. And distances are so short that you can easily get to almost all of the city’s main attractions without ever needing to drive or get an Uber. 

The Best Things to See Within Walking Distance of Key West

Despite its small size, Key West boasts an impressive array of interesting things to do, especially in Old Town. You can get to most of them without a car, which is another reason that the Conch Republic (as Key West is lovingly called) is one of the best walkable cities in Florida. One option is to simply wander around, seeing where the wind blows and where destiny takes you. If you want an itinerary to hit up all the best things to do in Key West, I’d walk from the Atlantic Ocean to the Gulf Coast in what locals playfully call “the longest walk in the world.” 

Without stopping, this will take around 30 minutes, but the idea is to sightsee along the way. Start at the unmissable Southernmost Point marker and get fuel at the Southernmost Beach Cafe’s quick-serve window. From there, start heading west up Whitehead Street. You’ll pass by lovely historic homes in pastel colors, small family-owned businesses, and groups of tourists and locals walking around the city. Along the way, look for the iconic wild roosters that often hold up traffic as they take their time crossing the street.

If you like history, your first stop should be the Hemingway Home and Museum, where the legendary author lived in the 1930s. The Key West Lighthouse is also nearby, as is Blue Haven, whose sky-high Key lime pie has a cult following. Consider stopping by at other historic spots like the Audubon House and Historic Gardens or the Key West Museum of Art History at the Custom House. Otherwise, simply take in your surroundings as you continue walking along to Mallory Square. You can spend the rest of the day shopping, drinking mojitos at El Mesón de Pepe Cuban restaurant, or getting some of the city’s freshest seafood at Conch Republic. If you like your pie more tart than sweet, then this is also your moment to go into Kermit’s for a slice.

Make sure you’re back at Mallory Square to catch the sunset. It’ll be crowded, but worth it. Once the night’s begun, head back down east on Duval Street, Key West’s main entertainment spot. Here, you’ll see everything from kitschy souvenir shops selling t-shirts to fine art galleries and fancy restaurants. Take it all in, and consider going into some of the street's most legendary bars like Sloppy Joe’s, Captain Tony’s, or Willie T’s for a raucous yet welcoming dive bar vibe.

Tips for Visiting Key West Without a Car

Even though you don’t need a car to explore Key West, a road trip south will take you on a scenic drive along the Overseas Highway that connects the Keys to the mainland. Once in the city, choose your hotel wisely. I’ve stayed in different parts of town, and my favorite accommodation has been without a doubt the Southernmost Beach Resort. Set right next to the Southernmost Point marker, the hotel’s location couldn’t be more convenient. It’s at the very end of Duval, so you’ll be within walking distance of the bars and restaurants, but just far enough to be able to enjoy some peace at the beach if you prefer that. The hotel also rents out bikes, which my mom and I used to explore around a bit during a recent trip. If you’d rather stay elsewhere, I would highly recommend looking exclusively at hotels in Old Town, especially if you want to walk more often than drive. 

Wherever you stay and whatever you do, take the intensity of the sun into account. The Florida heat doesn’t play, and neither should you. If you plan to walk around during the day, hydrate often and consider getting a portable fan or a UV-protectant umbrella. You could also make the most of the early morning and late afternoon/night, and leave the middle of the day for lounging by the pool or swimming in the ocean.

Key West will always be one of my favorite places in Florida—perhaps even the entire country. I love its laid-back vibe, its willingness to embrace its wonderful weirdness, its constant proximity to the water, and, of course, its walkability. There's simply something irresistible about a city that centers people rather than cars, and the Conch Republic knows this well.