Behind its candy-colored houses and swaying palm trees, Key West holds a quirky culture and deep history that will intrigue even the most seasoned traveler. Only in Key West can you explore a shipwreck a hundred feet underwater, lounge on a beach next to a Civil War-era fort, and sip rum at one of Hemingway’s favorite bars—all in the same day.
Immerse yourself in one of the Keys’ most important habitats with a paddle through the mangroves. With the water inches below and mangrove trees stretching in from both sides, you’ll have a front-row seat to the fish, crustaceans, sponges, and birds that call the mangroves home. Lazy Dog Adventures offers multiple options, including a four-hour kayak tour with snorkeling.
The world’s third largest barrier reef (and only coral barrier reef in the continental U.S.) is in South Florida. The waters of the Florida Keys are home to coral reefs, mangroves, and seagrass beds teeming with over 6,000 species of marine life. Dive and snorkel operators like Southpoint Divers in Key West can get you up close and personal with local marine residents like turtles, sharks, and dolphins.
Dry Tortugas National Park is accessible only by boat or seaplane—but it’s well worth the trip. The park is home to Fort Jefferson, a 19th-century fort called the “Guardian of the Gulf,” surrounded by sparkling blue waters teeming with tropical fish. Explore the fort, then don your snorkel gear to check out the coral reefs and seagrass beds below the surface.
Best Day Trip
Take the Overseas Highway a hundred miles north for spectacular views and classic roadside attractions. Enjoy panoramic ocean scenes on the Seven Mile Bridge as you head to Marathon, where you can see rehabilitated sea turtles at the Turtle Hospital. Grab souvenirs at Islamorada’s Rain Barrel Artisan Village before sampling key lime pie at the Fish House in Key Largo.
Off the Beaten Path
Fort Zachary Taylor Historic State Park is home to Key West’s best beach, well worth the two-mile trek from downtown. Visitors can snorkel to see colorful fish and soft corals, or walk through nature trails to see birds and native plants. After lunch at the Cayo Hueso Café, tour the Civil War-era fort to see excavated cannons and ammunition. There’s a park entrance fee based on number of vehicles, so carpool if you can.
Most Iconic Place
Ernest Hemingway penned some of his most iconic works during the decade he lived in Key West. At the Ernest Hemingway Home and Museum, explore the studio where he produced 70 percent of his writing, including “The Snows of Kilimanjaro” and For Whom the Bell Tolls. Take a 30-minute guided tour and visit with the 40-some six-toed cats that roam the property, some descended from Hemingway’s own six-toed kitty, Snow White.
Duval Street is the go-to spot for Key West nightlife. This iconic strip lights up after sunset as bars turn on the neon and crank up the music. Stop at Sloppy Joe’s, famous for being frequented by Hemingway, then hop over to the Hog’s Breath Saloon. If you want to go off Duval, try the Green Parrot—it’s a local favorite.
President Harry S. Truman began using a former naval station headquarters in Key West as his winter retreat in 1946. He spent a total of 175 days at the “Little White House” and considered Key West his second favorite place in the world, behind his hometown. Tour the estate and gardens to learn about Truman’s presidential and personal history.
In 1982, U.S. Border Patrol set up a blockade on Route 1 in Key West to prevent undocumented immigrants from coming, resulting in massive traffic delays. In response, the town seceded from the Union, declared war, then immediately surrendered and called for foreign aid. The Conch Republic was born, and its navy conch flag can be seen throughout town.
The famous Mallory Square Sunset Celebration begins two hours before sunset, complete with local musicians, artists, and food vendors. It’s the performers that steal the show, though—from Dale the Sword Swallower to Dominique the Cat Man (whose act includes kittens on a tightrope). It’s an experience that needs to be seen to be believed.