Your Trip to Key West: The Complete Guide

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The nation’s southernmost city is filled with fun bars, restaurants, historic homes and museums, beaches, watersports and eclectic characters with stories to tell. A three-hour trip from Miami (you can also fly into Key West International Airport), the drive to Cayo Hueso is anything but stressful when you’re surrounded by crystal blue, sparkling waters on both sides of the highway. A therapeutic drive forces you to slow down and will get you in the mood for what’s to come—boozing, cruising, and possibly some dolphin-watching. Use this guide to plan your trip including where to stay, what to do, when to go, and more

Planning Your Trip

  • Best Time to Visit: Visit between March and May when the weather is milder for South Florida (think 70s and low 80s Fahrenheit and less humidity all around) and there aren't as many tourists.
  • Language: English, though there are many native Spanish speakers.
  • Currency: U.S. dollar.
  • Getting Around: You can rent a car in Key West or use a rideshare app, but a pretty common and somewhat adventurous way to get around Key West is on a Vespa. Many hotels on the island have rental programs for guests, as do local tour companies.
  • Travel Tip: If you’re not much of a scooter fan or even a bike rider, you can get around Key West perfectly fine on foot. Old Town is worth exploring at a leisurely pace, anyway. There’s a European-style (above ground) cemetery worth checking out and most of the restaurants, bars, and sights we’ve listed are easily accessible when you’re walking.   

Things to Do

Local bars stay open really late here, and most of them hire local talent to play originals, as well as covers of songs we all love. The Ernest Hemingway Home is a must-do, as is a photo at the Southernmost Point of the Continental U.S., an anchored concrete buoy by the water. The well-known tourist attraction has been at the corner of South and Whitehead Streets since 1983 and is the most visited and photographed attraction in the Keys.

  • You’ll likely end up on Duval Street at some point, where you'll find shopping, dining, and drinking galore.
  • Mallory Square is where a daily Sunset Celebration takes place with live entertainment that includes fire breathers and artists of all sorts.
  • If tours are more your speed, reserve a spot on the Ghosts and Gravestones trolley tour. Guides combine Key West history with some clever ways to make you scream, so this activity may not be suitable for children under the age of 13. 

Explore more attractions with our full-length article on the best things to do in the Florida Keys.

What to Eat and Drink

If you like seafood, you’re in the right place. It’s always fresh and always perfectly cooked. If you’d rather go fishing and present your catch at a restaurant, they’ll season and cook it for you. While you're in town you have to try a slice of Key lime pie. Some of our favorite restaurants in Key West include El Siboney (Cuban food), Eaton Street Seafood Market & Restaurant (go for the stone crabs), Half Shell Raw Bar (oysters, pelicans and the decor here will leave you wanting more) and Croissants de France (for a full-on carby French breakfast of crepes, fresh-baked pastries and French toast—with a side of eggs for balance).

When it comes to imbibing, the options are endless, but for craft cocktails, Caroline’s Other Side is a cozy, cool bar hidden in a Key West-style home. Breweries are abundant here, too. Waterfront Brewery and First Flight Island Restaurant & Brewery are a couple; there are also rum distilleries (Key West First Legal Rum Distillery) and the down and dirty, good old bars that haven’t changed since they opened, like Sloppy Joe’s, Green Parrot Bar, Capt Tony’s Saloon and El Meson de Pepe where you can dance nightly to the only salsa band on the island.

Where to Stay

Where do we begin? If you want to relax right outside town, there are some newly renovated and reopened hotels worth getting to know, like Havana Cabana, 24 North Hotel, the Perry Hotel Key West and the Gates Hotel. Smack in the middle of the downtown area, though, the possibilities are endless. La Concha Hotel & Spa serves up glamorous 1920s vibes (it opened nearly 100 years ago), Casa Marina Key West, a Waldorf Astoria Resort channels Old Hollywood but in Florida, and the Saint Hotel Key West, an Autograph Collection Hotel, feels dark and mysterious in all the right ways New Orleans might feel dark and mysterious. Old school bed and breakfasts are abundant in the Southernmost City, too, and there’s something refreshing about booking the old-fashioned way and having bread baskets delivered to your door in the morning.

Getting There

You can drive into town (there’s only one road on and off the island) or fly into Key West International Airport. While cars are helpful to get around, especially when traveling from one side of the island to the other, most areas are easily walkable. On the rare occasion you’re sailing around the world, or even just the state of Florida, you can dock nearly anywhere on the island. Some hotels give guests the option of parking their boat instead of a car.  

Money Saving Tips

Take advantage of parks and museums that are free of charge for all visitors. Walking, of course, is free, good for you, and a more affordable option than hopping in a rideshare car. If you and everyone in your crew is of legal drinking age, First Legal Rum Distillery offers free rum tastings, with the purchase of one shot glass per person. 

  • The Children’s Animal Park has a petting zoo, which will delight kiddos of all ages. 
  • The Florida Keys Eco-Discovery Center is another fun and educational place to learn about local plant and animal species. 
  • Higgs Beach is free to visit, too. Pack a blanket, a picnic, and lots of water, and spend the day soaking in the sun and saltwater. 
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