36 Hours
By Dave SeminaraJuly 17, 2025
By Dave Seminara Photographs by Scott McIntyre
Dave Seminara lives in St. Petersburg, Fla., and enjoys exploring the Keys.
Why did Key West, a city of 25,000 at the marshy tip of Florida, attract 4.6 million visitors last year? There are no theme parks, no golf courses, no casinos, and there are better beaches in far more obscure Florida cities. It’s probably the most charming, but unquestionably the least air-conditioned city in a state where frosty A.C. is a sacrament. The conchs, as islanders are called, are an eccentric lot who are passionate about preserving their hometown, which has one of the largest historic districts in the South and is one of the most gay-friendly cities in the country, with a large number of its residents identifying as L.G.B.T.Q. Allegations that Key West has become a paradise lost have swirled since at least 1929, when Harper’s published an essay asserting that the construction of the Overseas Highway into town would cause Key West to lose “half its charm.” But those charms — the Key lime pies, the white gingerbread houses hidden behind tropical gardens and the city’s live-and-let-live ethos — endure.
During the latter half of the 19th century, Key West was one of the richest cities in the nation. More than 160 factories produced 100 million cigars annually, and the city’s shipwrecking and sponge industries turned a former backwater into a boomtown. But by the Great Depression, these industries were dead, and the city declared bankruptcy in July 1934. At the Key West Museum of Art & History at the Custom House ($17), visitors can learn how Key West reinvented itself as an artsy tourist destination by enticing out-of-work artists to the city via the Federal Art Project. The museum’s well-air-conditioned first floor features works by Key West artists past and present, like Mario Sanchez, Suzie Zuzek de Poo and the writer Tennessee Williams, who turned to painting later in life as he battled depression and drug addiction.
Hop on a bike, either a rental (try Key-Lime Bike Rentals, $4 per hour) or a loaner from your hotel, and pedal over to the Key West Cemetery, the final resting place of hundreds of notable Key West residents along with nearly two dozen U.S. Navy sailors buried there after the explosion of the U.S.S. Maine in Havana Harbor in 1898. Pick up the free self-guided-tour brochure to help you locate tombstones with creative epitaphs, like that of B.P. “Pearl” Roberts (“I told you I was sick”), and notable residents, like Deputy Sheriff Frank E. Adams, an African American who was killed in 1902 while trying to make an arrest, and Wilhelmina Harvey, a trailblazing woman who was the first female mayor of Monroe County (which includes Key West). She made Queen Elizabeth II an “honorary conch” on a 1991 visit to the area and her epitaph describes her as an admiral in the Conch Republic Navy.
Paul and Evalena Worthington sailed into Key West on their boat, Schooner Defiance, on a stormy night in 1984. It was supposed to be a stop on the way to Australia, but instead they relocated and opened Schooner Wharf Bar, an unpretentious outdoor bar and restaurant at the Historic Seaport that bills itself as “the last little piece of Old Key West.” Get a table overlooking the harbor, with its beautiful boats, to catch the sunset before happy hour ($3 bottles of domestic beer, $4 glasses of wine) ends at 7 p.m. The portions are big enough that two people can share one mouthwatering red snapper meal ($26.95), which comes with three sides on a paper plate.
After dark, walk over to the Green Parrot, a beloved open-air bar with nightly live music that bills itself as a “sunny place for shady people.” Or if you want a cocktail with a view, try the outdoor bar Dorada, at Casa Marina, a historic oceanfront hotel dreamed up by Henry Flagler — a founding partner of Standard Oil, who helped turn Florida into a popular tourist destination — and opened in 1920.
Visitors and residents appreciate Key West’s live-and-let-live ethos.
Sandy’s Café
Hemingway once called Key West the “St.-Tropez of the poor,” but these days, the hunt for inexpensive meals there can feel like Jimmy Buffett’s hunt for a long-lost shaker of salt. The good news is that the city’s Cuban restaurants offer delicious food at reasonable prices. Sandy’s Café, a take-away spot with an outdoor counter that’s attached to a laundromat, is well known for its Cuban Mix sandwich ($9.75), but its iced café con leche ($3.95) and breakfast sandwiches ($6.25 to $9.75) are also excellent. If you want a sit-down breakfast, venture to nearby Stock Island, where El Mocho offers a $10 breakfast special that includes two eggs, bacon, sausage or ham, hash browns or grits, and freshly baked bread. Pick up a sandwich at either place to take on your fishing excursion.
Sandy’s Café
Regardless of whether you like Hemingway, you must tour the writer’s Key West home, built in 1851 and purchased for Hemingway and his second wife, Pauline, by her uncle for $8,000 in 1931. The tour guides are engaging, the wraparound porch and lush gardens are stunning, and the 57 cats on the premises, half of them six-toed descendants of ones the Hemingways owned and named after celebrities like Zsa Zsa Gabor and Babe Ruth, are worth the $19 price of admission. You’ll want photos of the pool, still the largest in the city and constructed at the behest of Pauline, much to Hemingway’s chagrin, on the site of his homemade boxing ring for the then outlandish price of $20,000. Another highlight of the tour is his writer’s studio, which still has his favorite Royal typewriter.
It was a world record back in 1938, when Hemingway caught seven marlins in one day — a feat you are unlikely to duplicate, though you can have fun trying. Plan in advance with the website Captain Experiences, which allows you to enter your date and what you’d like to catch and then shows you guides operating excursions that match your criteria, along with reviews. For $700, for instance, Screaming Line Adventures or Rusty’s Bucket Charters, run by two highly regarded local captains, offers a private fishing boat that can accommodate up to six people for a four-hour near-shore trip that includes a captain and everything you need to fish. Captain Conch Charters has four-hour, offshore split-charter excursions that cost $210 per person. (Split charters allow you to team up with other people looking to go out.) If you’re not into fishing, but want to help preserve the waterways around Key West, you can volunteer with the Conch Republic Marine Army, which operates volunteer trips (which last until 3 p.m.) on Wednesdays and Saturdays, to remove debris from the mangroves and shorelines near town.
Learn about one of the greatest hauls in maritime history at the Mel Fisher Maritime Museum ($17.50). It took the treasure hunter Mel Fisher nearly 16 years to find the Spanish galleon Nuestra Señora de Atocha, which sank near Key West in 1622. In 1975, his son, daughter-in-law and one crew member died when their boat sank while hunting for the treasure. But on July 20, 1985, he and his team finally hit pay dirt, discovering some $450 million worth of gold, silver and emeralds. The first floor of the museum recounts the seldom-told story of how the loss of the Atocha and two other ships led to the downfall of Spain as the world’s first superpower, while the second floor documents the history of the trans-Atlantic slave trade in harrowing detail.
The Gallery on Greene
If you want to meet a quintessential conch, visit the Gallery on Greene and talk to its owner, Nance Frank. She can tell you about the time she navigated a 30-foot sloop around Cape Horn without an engine and give you the backstory behind her remarkable collection of fine art, which includes works by Mario Sanchez, Peter Vey, Suzie Zuzek de Poo and other Key West artists. Float Key West is a women’s boutique that sells “splurge worthy” clothing, hats, bags and jewelry. On the other end of the attire spectrum, Key West easily leads the nation in raunchy T-shirts and hats; you’ll find some at Nu Shuz, which stocks drag costumes and Pride-themed attire adjacent to MAGA-themed swag.
The Gallery on Greene
Hunter S. Thompson arrived in Key West in the 1970s at the behest of his friend Jimmy Buffett. He offered “gonzo tours” of the city, promising to show visitors “the dark underbelly of Key West.” Most of those haunts are long gone, but Louie’s Backyard and its oceanfront Afterdeck bar, memorialized in Buffett’s song “Trying to Reason With Hurricane Season,” endure. It’s now a much more upmarket affair, with its signature $44 Gulf shrimp and grits with bacon and mushrooms. For a more budget-friendly alternative, try the original Catherine Street location of El Siboney, a delightfully old-school Cuban restaurant with excellent sangria. The food is delicious, the portions huge — two can share the grilled-chicken platter ($18.95), with rice, beans and plantains. Tourists often spend hours waiting in line to order $13 slices of Key lime pie at Blue Heaven, another Buffett haunt, but some swear that El Siboney’s $5.95 slices are better.
Capt. Tony’s Saloon
William Hackley, a Key West lawyer, complained in 1830 that Key West was full of vagabond sailors who “are usually drunk from the time of their arrival to their departure.” The city’s reputation endures; visitors today are greeted at the airport with billboards for the Hangover Hospital, which offers 45-minute IV therapy “cures,” and the Garden of Eden, a clothing-optional bar. Boozy Duval Street is touristy but fun, so follow your ears to bars like the raucous Irish Kevin’s, which has live music nightly. Off Duval, Hog’s Breath Saloon “installs and services hangovers” and books quality bands, and General Horseplay has an air-conditioned bar, an outdoor bar with D.J.s and an upstairs speakeasy-style space. Capt. Tony’s Saloon, where Hemingway drank when it was called Sloppy Joe’s, is a delightfully dark old pub in a building that dates to 1851 and once served as the city icehouse and morgue.
Capt. Tony’s Saloon
Capturing the sunset at Simonton Street Beach.
Latitudes
For a memorable breakfast and rock star service, book the first reservation of the morning at Latitudes, a beachfront restaurant that is open to the public at the Sunset Key Cottages resort on Sunset Key, a private island that’s a six-minute ferry ride from Key West (the fare is included in the price of your meal). The Key lime French toast ($18) is served with Key lime custard, banana, toasted coconut flakes and fresh lime zest. If you’d like to get an earlier start, try Harpoon Harry’s, a beloved, cash-only diner that serves breakfast all day and is close to the seaport. Try the lobster Benedict ($22.95).
Latitudes
Part of the scheme to transform Key West into a tourist town in 1934 was to persuade locals to wear Bermuda shorts and ride bicycles. Nearly a century later, Key West is still best explored on a bike. Lloyd’s Tropical Bike Tours offers a popular daily bike tour. You can also create your own by downloading the free Key West Walking Tours app. The Cuban heritage tour will take you to old cigar factories; Gato Village Pocket Park, which has the world’s largest cigar sculpture; and the San Carlos Institute, where Cuban exiles planned the campaign to gain independence from Spain in the late 19th century. Meanwhile, the Black heritage tour will brief you on historic Black churches and important civil rights landmarks like the Martin Luther King Pool & Community Center, and will introduce you to notable African American conchs like Bishop Albert Kee, a beloved preacher who used to greet tourists at the city’s southernmost point buoy and teach them how to blow a conch shell.
Several American presidents have vacationed in Key West over the years — F.D.R., Dwight Eisenhower, J.F.K., Jimmy Carter and Bill Clinton, among others. But none were quite so addicted to the place as Harry S. Truman, who used what was once a naval officers’ home built in 1890 as his base for 11 working vacations, spanning 175 days during his presidency. Take a guided tour of the Harry S. Truman Little White House ($22.75), where you’ll hear stories about how Truman mulled over the Marshall Plan, the Truman Doctrine and the recognition of the State of Israel while on the premises. Make time to wander around the surrounding Truman Annex, which is a kind of tropical paradise of palm and banyan trees flanked by white gingerbread houses.
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