When you enter Key West, you’ll instantly feel the difference 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, combined with its accepting nature, makes 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.
Key West is closer to Cuba than it is to Miami, and this shines through in its culture and cuisine. 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. Just a short jaunt away in the Old Town, the 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. Nights don’t kick off until Sunset Celebration at Mallory Square, so be sure to arrive early and take part in the festivities before the show begins. You'll be in for a picturesque sunset that is definitely photo-worthy.
Key West’s cuisine is famous for a number of reasons, but seafood is high on the list. Since you're on an island, you’ll find a plethora of fresh seafood, especially stone crab, lobster, fish, and conch. Key West’s restaurants serve up conch in a variety of ways, from conch chowder to fried conch fritters. The island also boasts a variety of international flavors—especially Cuban, following emigration to the area in the early 1800s. 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, and many shops claim to serve the best one in town.
Key West exudes a Mardi Gras-like atmosphere, especially during festivals. While you can see this year-round at the bars in town and at the Sunset Celebration with its sword swallowers and fire jugglers, the best way to soak in the culture is at one of the city's annual parties, like Fantasy Fest, a precursor to Halloween. The festivities include everything from a royal coronation ball crowning the Conch King and Conch Queen to drag queen contests, pet masquerade costume contests, and The Fantasy Fest Parade. In July, the city honors writer Ernest Hemingway during the annual Hemingway Days Festival with a lookalike contest at one of his local haunts, Sloppy Joe’s.
Strolling along Duval Street, the main drag in Key West, you’ll come across plenty of local boutiques and galleries with an eclectic selection. The Green Pineapple is one example, with a marketplace vibe featuring clothing and eco-friendly gifts, as well as the Lush Bar, serving up organic coffee and tea, wine, and chocolates. Another pick that locals love is Bésame Mucho, a shop that doubles as a gourmet store in the Bahama Village neighborhood. Go gallery-hopping along upper Duval Street and get a sense of the local art in the form of paintings, jewelry, and glass, as well as a unique selection of furniture from around the world.
While the weather is generally warm year round, the best time to visit Key West is during the dry season, from November through April. 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.