The Best Things to Do in Key West

New Orleans may be home to America’s most festive thoroughfare, Bourbon Street, but Key West’s Duval Street is a close second. This two-kilometer-long (1.25-mile-long) road runs from north to south, from one end of the island to the other, and passes through the city’s historic Old Town. It’s lined with bars, restaurants, stores and galleries—many of which are among Key West’s most famous, including Sloppy Joe’s, a Hemingway hangout back in the 1930s and still a hotspot today. By day it’s mostly for shoppers, but it really heats up at night, with huge crowds strolling up and down the street, live music spilling out from the bars and a party atmosphere all around.

Yes, there is a fort here—a National Historic Landmark built in the mid-1800s to protect the country’s southernmost coastline—but locals know it for its excellent beach. A nice sandy expanse is a rarity in the Florida Keys—they’re surrounded by coral reefs, which make for primo fishing and diving but block the waves that are needed to produce a proper beach. But here, sand is trucked in to create a close facsimile—plus the water is wonderfully clear and calm, and there’s great snorkeling thanks to an offshore reef.

The Key West Shipwreck Museum transports visitors back to 1856, when the young city’s port had more than 100 ships passing through daily. Because of the coral reefs, shipwrecks were common at the time and salvage became a thriving business. At the museum, visitors will meet an actor portraying Asa Tift, an actual Key West citizen whose family made a good living salvaging, or saving, crew, passengers, and cargo from ships that were wrecked on the reefs. He’ll tell the stories of the many wrecks and recoveries of Tift’s time. The museum’s immersive experience includes films and historic artifacts, including the wreckage of the Isaac Allerton, which sank off the coast in 1895.

Key West’s most famous literary resident, Ernest Hemingway, lived in this two-story Spanish-colonial villa for nearly a decade and composed several of his best-known works here. His second wife, Pauline, insisted they add a pool to the spacious grounds—the first inground pool in Key West. The cost ballooned to around $20,000, a fortune in the 1930s, and was said to have contributed to the breakup of their marriage. It’s just one of the fascinating stories guides will share on the half-hour tour of the home and gardens (included in the price of admission). And yes, you’re guaranteed to see plenty of six-toed cats, descendants of Hemingway’s original six-toed cat, Snow White.

Key West is billed as “the Home of the Sunset,” which means every time the sun sinks below the horizon, it’s time for a party. Since the 1960s, Mallory Square’s dock has been hosting this nightly celebration, which begins two hours ahead of sunset with jugglers, musicians, artists, and street performers showing off their talents while food carts serve up conch fritters and Key lime pie. Soak up the quirky scene while waiting for the big show in the sky.

The city of Key West has an incredible literary history, and one of its most celebrated residents was Tennessee Williams, who lived in town from 1941 until his death in 1983. A final draft of his most famous play, A Streetcar Named Desire, was written at La Concha Hotel here in 1947. Williams later bought and moved into a cottage in town. The exhibit, in another lovely yellow cottage, displays movie posters, newspaper articles, photos, first editions, and memorabilia like his vintage typewriters. The free exhibit is manned by friendly volunteers and is open from 10 a.m. to 5 p.m.

The Southernmost Point buoy, at the corner of Whitehead Street and South Street, marks not only the spot for the southernmost point of the continental United States but also the distance (90 miles) to the next country, Cuba. The buoy, installed by the city in 1983, is visited by thousands of people each day. (Before the buoy, a small sign stood at the spot alongside a line of seashells for purchase.) Taking a photo in front of the buoy is imperative for a first visit to Key West, so bring a tripod, or ask a stranger to snap a few shots. Buskers play music, and street vendors sell food and goofy souvenirs and slash open coconuts to drink.

It is irresistibly tempting to compare distiller Paul Menta to Captain Jack Sparrow. There’s the long, dark hair, the slightly Depp-ish eyes, and yes, a shared love of rum and open sea (Menta’s a competitive kiteboarder). Menta’s business dealings, however, are a bit more…legitimate. The Florida-native opened the Key West Legal Rum Distillery last year, the first legal distillery in the Florida Keys, though rum has flowed through the islands for years. But this is no bathtub rum. A chef by trade, Menta uses Florida sugar cane as his base—you can really taste it in his raw, unfiltered version—which he infuses with coconut, vanilla, and key lime to make flavored rums that are refreshingly bright (and not syrupy). Tours are fun and informative—the distillery, occupying a former saloon-turned-Coke-bottling-plant, doesn’t shy away from the shady side of the local rum trade. Visitors can examine mug shots of infamous local rum-runners, watch as prefiltered rum is drained into the still, and taste Menta’s five spirits. $8, including four tasters and a free shot glass.

This wood house was originally intended as officers’ housing on the island’s naval base, but became famous as the Little White House when Harry S. Truman used it as a base of operations for several extended stays during his presidency. The house, now a museum, is dedicated to the history that took place here: Not just Truman, but Thomas Edison and presidents Taft, Eisenhower, Kennedy, Carter, and Clinton all spent time here, and several key summits took place here as well. As you walk through the house you’ll view all of the original furniture and historical elements—including Truman’s famous “The Buck Stops Here” desk sign—which have been maintained for generations. The beautiful tropical garden is surrounded by the original 1890 wrought-iron fence.

The San Carlos Institute was founded in 1871 by Cuban exiles who came to Key West to campaign for Cuba’s freedom from Spain. The original building was elsewhere and burned to the ground. The present building was erected in 1890. The interior was restored recently and the hand painted floor tiles and those in the main staircase area are works of art in themselves. The museum has exhibits and displays of pictures and historical articles of Cuban life in the 19th century and up until today. Stand outside and look at all the angles and balconies of this building. It’s a real piece of architectural history there in Key West. Admission is free; the museum is open from Friday - Sunday from 12 - 6.