Situated closer to Cuba than to Miami, Key West, Florida, offers a little slice of island life within the continental United States. Alongside gorgeous palm tree-studded streets, century-old mansions, and enough rum to fill several large ships, this laid-back town is home to many cultural, culinary, and adventurous activities for all types of travelers to enjoy.
Travelers can fly direct into Key West International from several major U.S. cities. Still, many visitors opt to fly into mainland South Florida and drive the famed Florida Keys Overseas Highway to enjoy its breathtaking ocean views. However you get to Key West, these are the activities that need to be on your itinerary.
Get a Taste of Literary History at the Ernest Hemingway Home
This small island is said to have inspired more writers per capita than any other city in the country, and the most well-known among them is undoubtedly Ernest Hemingway, whose former home is a must-visit for any fan of the author. The bright yellow Spanish colonial villa was Hemingway’s residence in the 1930s, where he wrote some of his most famous works. If you’re allergic to cats, beware: the grounds are home to more than 50 felines, all of which are descendants of a cat owned by Hemingway.
Drink Incredible Coffee at Cuban Coffee Queen
If you’re a coffee snob looking for a jolt, a trip to Key West wouldn’t be complete without a trip to the Cuban Coffee Queen. Home to a large Cuban population, south Florida runs on Cuban coffee, a bold, dark roasted blend of espresso brewed with ample sugar that will get your heart pumping faster in seconds. Head to Cuban Coffee Queen’s downtown street shack and order a cafe con leche—it’s the best version that you can find outside of Havana.
Eat Great Seafood
Key West’s culinary influences and offerings are diverse, but the crown jewel of the dining scene in this town is its seafood. Local favorites include shrimp, Florida spiny lobster, fish, and stone crab claws, considered a renewable resource because of the crabs’ ability to re-grow harvested claws. Some species, such as stone crab claws and lobster, are subject to seasonal harvest restrictions. A slice of Key lime pie, the Keys' signature dessert, is an ideal end to a meal.
Go Gallery Hopping
Key West may be known for its literary connections, but a flourishing visual arts community is evidenced by the many galleries exhibiting artwork in varying styles and mediums. Make an afternoon of it by perusing local favorites Gallery on Greene, Gingerbread Square Gallery, Frangipani Gallery, and Art@830.
Visit the Tennessee Williams Museum
Known as one of the greatest 20th-century playwrights, Tennessee Williams also called Key West his home for many years; in fact, it’s been said that he wrote the final draft of his masterpiece "Cat on a Hot Tin Roof" during his stay. A museum dedicated to his time in the Keys is located in the Duncan Street home that Williams purchased in 1950 and features rare memorabilia of his storied career.
Snap a Photo at the Southernmost Point of the United States
One of the most recognizable images of the Keys, the yellow, black, and red buoy-shaped structure that stands at the corner of South and Whitehead street is a photo opp that shouldn’t be missed. The marker indicates the 90-mile distance that stands between Key West and the next closest city, Havana, Cuba.
Learn About the History of the Key West Lighthouse
First opened in 1848 with a woman as its keeper, this lighthouse guided mariners through the region’s treacherous waters until it was decommissioned in 1969. The only U.S. lighthouse within city limits, it stands right beside the keepers’ quarters building. Visitors to its museum can learn the stories of the men and women whose job it was to keep its light burning.
Visit the Mel Fisher Maritime Museum
Mel Fisher, a longtime resident who died in 1998, led efforts to recover approximately $450 million in gold and silver from the Nuestra Señora de Atocha, a 17th-century Spanish galleon that sank 35 miles southwest of Key West. Fisher, who spent 16 years searching for the shipwreck, established the Mel Fisher Maritime Museum, where visitors can view and learn about the riches of the Atocha and other area shipwrecks, including the galleon Santa Margarita.
See a Drag Show
One of the most LGBT-friendly cities in the United States, Key West is home to many excellent gay bars and gay-themed entertainment. Head to the “Pink Triangle” on Duval Street to find regularly scheduled drag shows at Aqua, La Te Da, and the 801 Bourbon Bar, which hosts an annual nationally-televised New Year’s Eve “shoe drop” starring a local celebrity drag queen named Sushi.
Visit Key West's Very Own White House
Florida’s only presidential museum, the Truman White House, first served as the winter residence of President Harry Truman in 1946 and was the U.S. naval station’s command headquarters during the Spanish-American War, World War I and World War II. The house has hosted former presidents Dwight Eisenhower, John Kennedy, Jimmy Carter, and Bill Clinton.
Go on a Key Lime Pie Crawl
Key lime pie is a staple of the Keys, and having a slice (or five) during your visit is essential. Start at Blue Heaven, also home to Ernest Hemingway’s former boxing ring, for its famous sky-high slice, then continue to Kermit’s, Old Town Bakery, and La Grignote. Be prepared to pick a side in the ultimate Key West debate: whipped cream versus meringue topping.
Have a Sloppy Joe at Sloppy Joe's
While the origins of the sloppy joe sandwich continue to be up for debate, many foodies contend that the sandwich was born in Havana, Cuba—served with ropa vieja in an establishment frequented by sailors that had a "sloppy" reputation—and finessed at Sloppy Joe’s in Key West, a bar once owned by Ernest Hemingway. Order a rum cocktail and dig into this delightfully meaty treat.
Bar Crawl Down Duval Street
Nightlife in Key West is always lively and exciting. The "Duval Crawl" is a famous phrase used to describe fun-seekers' evening adventures up and down the island's main street to sample numerous taverns and entertainment offerings, including live music and drag shows. Some classic bars to hit are Green Parrot Bar, Smokin’ Tuna Saloon, The Garden of Eden, Little Room Jazz Club, and The Rum Bar.
Drink Rum Like Hemingway
Key West’s Bahamian heritage is evidenced throughout the island, but perhaps nowhere more so than in its excellent rum selection. If you’re looking to quench your thirst, Key West First Legal Rum Distillery offers a variety of flavored rums aged in salt-cured barrels. Nearby, Hemingway Rum Co. Distillery, an 8,200-square-foot brick distillery, and attraction with photo tributes to Ernest Hemingway, produces up to 80 gallons of rum daily from molasses, yeast, and water.
Catch the Sunset at Mallory Square
At each day's end, crowds gather at Key West’s central Mallory Square to take in the nightly "sunset celebration," a tradition that both locals and visitors look forward to daily. While musicians, acrobats, and other performers provide entertainment on the boardwalk, the sun sinks slowly below the horizon as sunset cruise boats sail by in Key West Harbor.