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

Florida is a wonderful state, but it's not a walkable one. Like most of the U.S., many of our cities were developed after cars were invented and were built around motor transportation rather than walkability. We also have a tiny issue called heat, which can get so intense that it often feels impossible to be outside unless you can cool off in the sea. Yet there’s a tiny little town at the tip of the peninsula that is blissfully free from the constraints of car-obsessed American culture. Here, people walk or bike around and spend time outdoors rather than hiding from the sun. Their secret? Living on an island small enough to be entirely explored on foot. I’m speaking, of course, of quirky Key West, which might just be the most walkable city in all of Florida. 

Why This Florida City 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, of neighbors who know each other’s names and 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

In Key West, there are so many things to do in the walkable Old Town that the real dilemma is which ones to prioritize. One option is to simply get lost and walk 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 also enjoying the city by foot. 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 legendary 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, 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 the 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, you'll want to drive into the city after doing the 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 is simply something irresistible about a city centered around people rather than cars, making it one of the best walkable cities in Florida. Thankfully, the Conch Republic figured that out long ago and doesn't seem like it'll change anytime soon.