At a Glance
When you arrive in Key West—the southernmost point of the U.S. at the western end of the Florida keys—you’ll instantly feel its distance from the rest of Florida. The island’s colorful culture draws a diverse crowd of characters: from cruise ship passengers, families, and couples to spring breakers, artists, and drag queens. The city’s "anything goes" attitude and accepting nature make for a festive environment day and night. Whether you’re looking for a lively nightlife scene, museums and culture, or a day in the sun, Key West offers something for everyone.
When to Go
While the weather is generally warm year round, the best time to visit Key West is during the dry season, between November and April, but of course, winter is also high season, so room rates will be high. If you're looking for fewer people, days that aren't too hot, and decent hotel rates, visit between the rush of spring breakers and late May.
The Florida Keys are a 120-mile-long chain of islands extending south of Miami to Key West, so take the scenic route driving along the Overseas Highway’s 42 bridges. Domestic and international airlines offer flights to Miami International Airport, but you can also fly directly into Key West International Airport on a number of domestic airlines (Delta, United, American, and Silver Airways), or take a ferry from Fort Myers on Florida’s west coast. Since Key West is only a 2-by-4-mile island, you can skip driving and explore by foot, bike, or scooter.
The Florida Keys are a 120-mile-long chain of islands extending south of Miami to Key West, so take the scenic route driving along the Overseas Highway’s 42 bridges. Domestic and international airlines offer flights to Miami International Airport, but you can also fly directly into Key West International Airport on a number of domestic flights, or take a ferry from Florida’s west coast. Since Key West is only a 2-by-4-mile island, you can skip driving and explore by bike or scooter.
Key West is closer to Cuba than it is to Miami, and this geographical blessing shines through in its culture and cuisine. To honor that connection, make your way to the iconic Southernmost Point marker that marks 90 miles to Cuba. First-time visitors shouldn’t miss the home of one of Key West’s most celebrated residents—the Ernest Hemingway Home and Museum. The Old Town house looks exactly how it did when the writer resided in the Conch Republic, and descendants of his six-toed cat Snowball still roam the grounds. Night doesn’t really start until it's kicked off by the Sunset Celebration at Mallory Square, so be sure to arrive early for the show. You can expect not just a picturesque sunset but also a distinctly Key West-flavored event.
Food and Drink
Key West’s cuisine is famous for a number of reasons, not least of which is seafood. On the island's menus, you’ll find a wealth fresh seafood, especially stone crab, lobster, fish, and conch. Key West’s restaurants prepare conch in a variety of ways, from chowder to fritters. Enjoy a typical Cuban breakfast of toasted bread and a cafecito (Cuban coffee with sugar), or pick up a pressed Cuban sandwich filled with ham and cheese. The dining experience in Key West wouldn’t be complete without key lime pie: Since several shops claim to serve the best one in town, you should sample them and decide for yourself.
Key West’s Mardi Gras atmosphere permeates the island year-round and can be experienced on any given day by heading into one of the Old Town bars or by attending the Sunset Celebration along with sword-swallowers and fire-jugglers. But the best way to soak in the local culture is by visiting during one of the city's annual parties. But the best way to soak in the local culture is by visiting during one of the city's annual parties. At Fantasy Fest, a precursor to Halloween, the festivities include a royal coronation ball at which the Conch King and Conch Queen are crowned, as well as drag queen contests, competitions for best pet costume, and the Fantasy Fest Parade. Each July, the city honors writer Ernest Hemingway during Hemingway Days Festival which feature readings and panel discussions, a parody of Pamplona, Spain’s running of the bulls, and culminates in a Hemingway lookalike contest at one of his old haunts, Sloppy Joe’s.
Along Duval Street, the main drag in Key West, you’ll come across plenty of local boutiques and galleries with an eclectic (and often cheesy) selection. The Green Pineapple has a marketplace vibe and features bohemian clothing and eco-friendly gifts. Lush Bar Key West serves up organic coffee and tea, wine, and chocolates. On Petronia Street, the gift shop Bésame Mucho doubles as a gourmet store that locals frequent. Go gallery-hopping along upper Duval Street and get a sense of the local art in the form of paintings, jewelry, and art glass, as well as a unique selection of furniture from around the world.