Key West

When browsing through our list of best things to do in Key West, keep in mind that the island city is closer to Cuba than it is to any single Walmart. True story. The 48 bridges that connect Key West to the mainland of Florida (including the Walmart 129 miles away, in Florida City) do more than just bring power, water and tourists to the area: they serve as a separation from life on the mainland. Each bridge crossed takes you closer to the idyllic island living that locals so adore. So, when here, do as the locals do: hop on a bike, pedal to your destination (from restaurants to bars and beaches) rain or shine and cruise past the roosters, iguanas and six-toed cats that also reside in the lush, historic streets of Old Town. In spite of the slower pace, there is still much to do in Key West: a variety of outdoor activities is complemented by five theaters, an independent movie house, numerous galleries chock full of fine art created by locals and, of course, imbibing and dining destinations that range in style and scope, most home to musicians that play their unique tunes from happy hour until late at night daily.

June 2019: We’ve updated our list of the best Key West restaurants for summer to include some new and old favorites that well-deserve the nod of notoriety. From new digs for must-sup staples, like Onlywood (#13) and the Flaming Buoy (#12), to new chefs and revamped menus (Marquesa at #1) and even newer town additions like Dirty Pig (#18), The Jerk (#20) and Little Pearl (#3). Whether you want to sink into a sandy spot beneath a banyon tree where the ubiquitous chickens roam free or want a ringside seat for sunset dining, we’ve got your covered. There’s a perception that things don’t move quickly in Key West, but the Conch Republic is far from immune to the winds of change – especially since 2017’s Hurricane Irma blew through town. While some spots like 2 Cent, Pescado and Cuzzy Bubbaz sadly shuttered (either as a direct result or financial fall-out of that storm), others turned key limes into limeade, changing locales, bringing in new talent or finding opportunity to strike out with something new altogether. Of course, with its proximity to both the Atlantic and the Gulf, locally caught, deliciously fresh seafood is king here. That eye towards sustainability is also what impacts the best things to do in town, local bars and even the way Key West beaches are taken care of. From the famed, ubiquitous grouper and mahi mahi, to mutton and yellowtail snapper, hogfish and lionfish (an invasive predator fish that more and more chefs are finding delicious use for), and the Key West pink shrimp, crab and spiny lobsters, water-bound creatures are the local protein of choice, although a slow-burn of barbecue spots popping up from Old Town to Uptown are a trend to keep an eye on as well. There’s a natural gravitation toward Caribbean flavors and a casual, flip-flops-encouraged dress code that’s long ruled the day and night. But spots like Little Pearl, Thirsty Mermaid and Nine One Five are bringing a new era of bright, fresh, less-is-more flavor to town, allowing the great local fare to take the star turn over heavy sauces or the confines of a frialator – same for revamped wine and cocktails lists that are venturing away from stale, sweet hit-parade pariahs. Key West was, is and, if it doesn’t become part of the ocean, always will be a vortex of creativity. To help you navigate it all, we break down the best eateries in town.

Arriving at the Key West International Airport, travelers are greeted by the sound of rustling palm trees and a delightful absence of crowds. It’s time to switch into a lower gear. Key West, famous for its plentiful things to do on land and in the water, its colorful Duval Street bars and restaurants and its splendid ocean outlooks, has been a dependable coastal escape for travelers of all walks of life. And at the best hotels in Key West, absolute relaxation is the number one concern. Here, we’ve rounded up blissful private cottages, rollicking oceanfront resorts and historic mansions remade as luxury inns. However you choose to unwind in America’s southernmost city, we’ve got you covered.  

Most of the best Key West beaches are tucked away like hidden treasures. After all, this is not your typical beach town: the velvety-smooth sand dotting our man-made island has been imported from the Atlantic Ocean, the Gulf of Mexico and beyond and has to be occasionally replenished. Each local swimming destination serves its own function: Fort Zack, where the Atlantic and Gulf meet, is the unofficial gathering place for birthdays, weddings and hangouts of any kind. On the ocean side, Smathers Beach is great for watching kiteboarders or even trying your hand at the sport yourself. Higgs Beach, also on the ocean side, is a sporty location where you can pick up a game of beach volleyball or train for your next triathlon by swimming laps between the piers in the ocean. And at the beach at Zero Simonton on the gulf side, you can relax and watch the sun set over the harbor accompanied by live music and cold beer. So, in-between gulping down delicious seafood at the best restaurants in Key West and craft beer from local bars, embrace one of the very best things to do in town: soak up that sun at these great local beaches. RECOMMENDED: Full guide to the best things to do in Key West

While it’s taken until recent years for this Florida Keys island to catch up to the cocktail renaissance happening elsewhere, the days of pre-fab sour mix and oxidized vermouth have been all but washed out to sea within the best Key West bars. Today, this southernmost U.S. island is as comfortable shaking up bespoke concoctions as it is dispensing frozen to-go piña coladas from open-air bars on devil-may-care Duval Street or the Last Call Bar at the tiny Key West airport. The thing about Key West is that the destination is comfortable with its own simplicity, offering timeless things to do, delicious restaurants and relaxing beaches, all of which contributes to a culture that allows for the beer-and-a-shot revelry of old haunts like the Green Parrot or Sloppy Joe’s to co-exist with serious drink destinations like Point Five Lounge and the brand new General Horseplay. Old Town is still where the brunt of the action is, but while Duval remains the city’s designated drag for cruise ship crawlers and weekend warriors, its high rents have spawned a swathe of new spots on side streets like Fleming and Caroline. Whether you’re looking for a casual stool from which to kick off your flip-flops and do a little margarita day-drinking, a low-key wine bar worthy of oenophile admiration or a sophisticated sunset perch to dive into a Hemingway daiquiri, our Key West list has got you covered.

Laidback island vibes, breathtaking sunsets and sweet tropical drinks have lured experience seekers to Key West for decades. But it’s the savvy travelers, the ones brave enough to veer away from the fray, who really get a feel for what this funky, way-down-south town is all about. Follow our guide to experience Key West like the natives (who proudly call themselves ‘conchs’). We’ll take you away from noisy Duval Street to explore cool under-the-radar haunts that offer everything Key West is known for—delicious drinks, catchy tunes and rowdy drag shows—but with a side of in-the-know, authentic local flair.

If you’re headed to Key West then you won’t be short of great Airbnb options. Yep, for such a small Key, the city is covered in an amazing number of apartments as well as a plethora of hotels, making it easy to stop by and check out the many brilliant things to do in Key West. And if you’re already local to the area? A weekend jaunt to Key West is a trip that every Floridian should take at least once in their lives (especially if your idea of a good getaway is all about beaches, bars and restaurants). So pack your bags – here are some awesome places to rest up during your vacation.