A funny but true story tells you all you need to know about the independent, larger-than-life spirit of tiny Key West, the 4-square-mile island at the southernmost tip of the Florida Keys. It was April 23, 1982, when, in search of illegal drugs, the U.S. Border Patrol set up a roadblock on US 1, the main thoroughfare connecting the keys to the mainland, creating a colossal traffic jam and hampering tourism. Key West city officials implored the federal government to remove the blockade but to no avail. So, they staged a mock secession from the Union, declaring Key West the Conch Republic. Within 60 seconds, they surrendered to the government and asked for a billion dollars in foreign aid. The money never materialized, of course, but the roadblock was removed—and the spirit of the story endures.
Today, locals continue to embrace their “sovereign state of mind” and tongue-in-cheek motto “We seceded where others have failed.” Indeed, along with a sense of humor, Key West brims with a singular sense of place, separated not only by the endless blue Gulf and Atlantic waters but also by its uniquely Conch come-as-you-are attitude and laid-back lifestyle.
If you long for a bit of island time but are short on—well, time, here’s a two-day itinerary that squeezes in a weekend’s worth of fun and sun in Key West. (You can sleep when you get home.)
DAY 1:
TOOLING AROUND TOWN
While Key West is super-walkable, consider renting transportation (an electric cart, a scooter or a bike, for example) to explore the island’s many corners. Another option: Board the Conch Tour Train or hop-on/hop-off Old Town Trolley to explore a greatest hits collection of attractions.
KEY WEST MUSEUMS
Love history? You’ll want to check out the Harry S. Truman Little White House, used as a retreat by Truman and five other US presidents during their presidencies, and the Key West Lighthouse & Keeper’s Quarters Museum, where you can explore the life of a keeper and climb 88 steps to the top of the 1848 lighthouse. Also, drop by the Oldest House Museum, a Bahamian-style home dating to 1829, and the 1891 Key West Museum of Art & History at the Custom House, featuring two floors of exhibitions.
You can also dive deep into the 19th-century Golden Age of Sail when a hundred ships passed by Key West daily, many wrecking along the treacherous reef, making the island a wrecking hot spot. Fascinating shipwreck stories are told at the Shipwreck Treasure Museum, also home to a 65-foot-tall lookout tower and artifacts salvaged from the Isaac Allerton, and the Mel Fisher Maritime Museum, showcasing treasure hunter Mel Fisher’s fortune of finds, including gold, silver and jewels from a 17th-century Spanish galleon.
KEY WEST MUSEUMS FOR LITERARY FANS
Key West has a storied reputation as a haven for the literati, with famous writers—including Mark Twain, Wallace Stevens, Robert Frost, Ralph Ellison, Elizabeth Bishop and Shel Silverstein–leaving their mark here. But the most legendary resident was Ernest Hemingway. His former home, a grand Spanish Colonial villa, is now the Ernest Hemingway Home & Museum. Here, you see the writing studio where he penned many a masterpiece and visit with some 60 six-toed cats, which are descendants of Hemingway’s pet feline. Nearby, the Tennessee Williams Museum presents a trove of artifacts related to the celebrated playwright.
KEY WEST GARDENS
If nature is your thing, head to The Key West Butterfly & Nature Conservancy, where a glass-domed tropical habitat teems with hundreds of fluttering butterflies, exotic birds and two flamingos. More glorious gardens await at the Audubon House & Tropical Gardens, Key West Tropical Forest & Botanical Garden, and West Martello Towers, a Civil War-era fort turned tropical oasis.
KEY WEST RESTAURANTS AND PLACES TO PARTY
Hungry yet? Key West’s multicultural influences translate to a kaleidoscope of island flavors, from Caribbean plates to Cuban specialties to American mainstays. For a quick bite, swing by the Bahama Village for curry- and jerk-infused Caribbean cuisine, the Cuban Coffee Queen for café con leche and Cuban sandwiches or, natch, Margaritaville for the quintessential Cheeseburger in Paradise.
Come evening, Mallory Square is the place to be beginning two hours before sunset. Here, on the promenade overlooking the Gulf of Mexico, a Sunset Celebration unfolds nightly, with magicians, acrobats and stunt performers entertaining the crowds as a prelude to the spectacular sunset.
KEY WEST SHOPS, ART GALLERIES, RESTAURANTS, AND BARS
Then, mosey over to Duvall Street, chockablock with shops, art galleries, restaurants and bars, many presenting live music nightly. Stop by Sloppy Joe’s, once a Hemingway hangout, for an original Sloppy Joe’s sandwich. Then, hop over to Captain Tony’s Saloon, where the late Jimmy Buffett performed and the dive-bar décor includes license plates, bras, business cards and dollar bills plastered everywhere.
DAY 2:
GETTING OUT ON THE WATER
You cannot visit Key West without getting out on that beautiful turquoise-blue water, of course. A slew of tour operators, many clustered along the Key West Historic Seaport, can take you out on everything from fishing charters to eco-adventures to sunset sails. The crystal-clear, calm waters are perfect for snorkeling, kayaking, paddle-boarding, jet-skiing, scuba-diving and more.
KEY WEST PARKS AND BEACHES
You can rent gear from tour operators on several public beaches, or simply enjoy a dip in the water at places like Fort Zachary Taylor Historic State Park, Smathers Beach and Higgs Beach.
For a splurge, take a day trip by high-speed ferry or seaplane to Dry Tortugas National Park, about 70 miles west of the island. Here, you can explore 19th-century Fort Jefferson as well as swim, snorkel and scuba to see an amazing array of marine life inhabiting the coral reef.
MORE TASTE-TEMPTING KEY WEST RESTAURANTS
Back at the dock, watch the boats unload their fresh catches of the day. Later, return here for dock-to-dish dining at the many restaurants dotting the seaport. You can’t go wrong with a waterside table at the open-air Conch Republic Seafood Company. For more upscale waterfront dining, make reservations for a balcony table at the A&B Lobster House. And save room for Key West’s iconic dessert: key lime pie. Kermit’s Key Lime Shop whips up some of the island’s best, including Key Lime Pie on a Stick.
Before wrapping up your whirlwind tour, snap a photo at the Southernmost Point, a concrete buoy marking, yep, the southernmost point in the continental US, a mere 90 miles from Cuba. And while you wave good-bye, remember to bring home the ultimate souvenir: some of that colorful Conch spirit.
