A '36 Hours' guide from The New York Times' Travel section.
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鈥檚 probably the most charming, but unquestionably the least air-conditioned, city in a state where frosty AC is a sacrament.
The conchs, as islanders are called, 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 LGBTQ+.
Claims that Key West has become a paradise lost have swirled since at least 1929, when an essay in Harper鈥檚 said the construction of the Overseas Highway into town would cause Key West to lose 鈥渉alf its charm.鈥� But those charms 鈥� the Key lime pies, the white gingerbread houses hidden behind tropical gardens and the city鈥檚 live-and-let-live ethos 鈥� endure.
ITINERARY
Friday
3 p.m. | Learn the back story
During the latter half of the 19th century, Key West was one of the nation鈥檚 richest cities. More than 160 factories produced 100 million cigars annually, and the city鈥檚 shipwrecking and sponge industries turned a former backwater into a boomtown. But by the Great Depression, these industries were dead, and in 1934 the city declared bankruptcy. 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鈥檚 first floor features works by Key West artists past and present, including Mario Sanchez, Suzie Zuzek de Poo and writer Tennessee Williams, who turned to painting later in life as he coped with depression and addiction.
5 p.m. | Read some epitaphs
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 Key West residents along with nearly two dozen U.S. Navy sailors buried there after the explosion of the USS Maine in Havana Harbor in 1898. Pick up the free self-guided-tour brochure to help you find tombstones with creative epitaphs, like that of B.P. 鈥淧earl鈥� Roberts (鈥淚 told you I was sick鈥�), and notable residents such as Wilhelmina Harvey, the first female mayor of Monroe County (which includes Key West).
6:30 p.m. | Enjoy sundowner time
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 opened Schooner Wharf Bar, an unpretentious outdoor bar and restaurant at the Historic Seaport that bills itself as 鈥渢he last little piece of Old Key West.鈥� Get a table overlooking the harbor 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.
8:30 p.m. | Jam to live music
After dark, walk over to the Green Parrot, an open-air bar with nightly live music that bills itself as a 鈥渟unny place for shady people.鈥� 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 鈥� a founding partner of Standard Oil, who helped turn Florida into a tourist destination 鈥� and opened in 1920.
Saturday
7:30 a.m. | Have Cuban cuisine
Hemingway once called Key West the 鈥淪t.-Tropez of the poor,鈥� but these days, the hunt for inexpensive meals there can feel like Jimmy Buffett鈥檚 hunt for a long-lost shaker of salt. The good news is that the city鈥檚 Cuban restaurants offer delicious food at reasonable prices. Sandy鈥檚 Caf茅, a takeout spot with an outdoor counter that鈥檚 attached to a laundromat, is known for its Cuban Mix sandwich ($9.75), but its iced caf茅 con leche ($3.95) and breakfast sandwiches ($6.25 to $9.75) are also excellent. For a sit-down breakfast, venture to nearby Stock Island, where El Mocho offers a $10 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.
9 a.m. | Meet Hemingway鈥檚 cats
Whether or not you like Hemingway, you must tour the writer鈥檚 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, are worth the $19 admission price. You鈥檒l want photos of the pool, still the largest in the city and constructed at Pauline鈥檚 behest, much to Hemingway鈥檚 chagrin, on the site of his homemade boxing ring.
10 a.m. | Go fishing
In 1938, Hemingway caught seven marlins in one day 鈥� a world-record feat you are unlikely to duplicate, though you can have fun trying. Plan ahead with the website Captain Experiences, which lets you enter your date and what you鈥檇 like to catch and then shows you guides operating excursions that match your criteria, along with reviews. For $700, Screaming Line Adventures or Rusty鈥檚 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 let you team up with other people looking to go out.) If you鈥檙e 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 (lasting until 3 p.m.) on Wednesdays and Saturdays, to remove debris from the mangroves and shorelines near town.
3:30 p.m. | Revel in treasure
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 Se帽ora de Atocha, which sank near Key West in 1622. In 1975, his son, his 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鈥檚 first superpower, while the second floor documents the history of the trans-Atlantic slave trade in harrowing detail.
4:30 p.m. | Check out local goods
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 back story behind her remarkable collection of fine art, which includes works by Key West artists. Float Key West is a women鈥檚 boutique that sells 鈥渟plurge worthy鈥� 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鈥檒l find some at Nu Shuz, which stocks drag costumes and Pride-themed attire next to MAGA-themed swag.
6 p.m. | Try shrimp and grits
Hunter S. Thompson arrived in Key West in the 1970s at the behest of his friend Jimmy Buffett. He offered 鈥済onzo tours鈥� of the city, promising to show visitors 鈥渢he dark underbelly of Key West.鈥� Most of those haunts are gone, but Louie鈥檚 Backyard and its oceanfront Afterdeck bar, memorialized in Buffett鈥檚 song 鈥淭rying to Reason With Hurricane Season,鈥� endure. It鈥檚 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 鈥� two can share the grilled-chicken platter ($18.95), with rice, beans and plantains. Tourists often spend hours in line to order $13 slices of Key lime pie at Blue Heaven, another Buffett haunt, but some swear that El Siboney鈥檚 $5.95 slices are better.
9 p.m. | Sample a bounty of bars
William Hackley, a Key West lawyer, complained in 1830 that Key West was full of vagabond sailors who 鈥渁re usually drunk from the time of their arrival to their departure.鈥� The city鈥檚 reputation endures; visitors today are greeted at the airport with billboards for the Hangover Hospital, which offers 45-minute IV therapy 鈥渃ures,鈥� 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鈥檚, which has live music nightly. Off Duval, Hog鈥檚 Breath Saloon 鈥渋nstalls and services hangovers鈥� and books quality bands, and General Horseplay has an air-conditioned bar, an outdoor bar with DJs and an upstairs speakeasy-style space. Capt. Tony鈥檚 Saloon, where Hemingway drank when it was called Sloppy Joe鈥檚, is a pub in a building that dates to 1851 and once served as the city icehouse and morgue.
Sunday
8:15 a.m. | Eat on a private island
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鈥檚 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鈥檇 like to get an earlier start, try Harpoon Harry鈥檚, a cash-only diner that serves breakfast all day and is close to the seaport. Try the lobster Benedict ($22.95).
9:30 a.m. | Get a history lesson
Part of the scheme to turn Key West into a tourist town in 1934 was to persuade locals to wear Bermuda shorts and ride bicycles. Today, Key West is still best explored on a bike. Lloyd鈥檚 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鈥檚 largest cigar sculpture; and the San Carlos Institute, where Cuban exiles planned the campaign to gain independence from Spain in the late 19th century. The Black heritage tour will brief you on historic Black churches and civil rights landmarks like the Martin Luther King Pool & Community Center, and will introduce you to African American conchs like Bishop Albert Kee, a preacher who used to greet tourists at the city鈥檚 southernmost point buoy and teach them how to blow a conch shell.
Noon | Mingle with presidents
Several American presidents have vacationed in Key West over the years. But none were quite so addicted to the place as Harry S. Truman, who used what was once a naval officers鈥� home, built in 1890, as his base for 11 working vacations. Take a guided tour of the Harry S. Truman Little White House ($22.75), where you鈥檒l 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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KEY STOPS
The Key West Museum of Art & History at the Custom House gives a great overview of Key West鈥檚 rich history, along with works by some of the island鈥檚 best artists.
Ernest Hemingway lived in Key West during the 1930s and wrote in what is now the Ernest Hemingway Home & Museum, which is also home to 57 cats, descendants of those the writer owned.
Visit the Mel Fisher Maritime Museum to see gold, silver and emerald treasures from the Spanish galleon Nuestra Se帽ora de Atocha, which sank near Key West in 1622.
WHERE TO EAT
Schooner Wharf Bar features tasty seafood, including fresh oysters, conch and catches of the day. It has a great happy hour and an unpretentious waterside setting.
El Mocho is a reasonably priced Cuban restaurant with on-point takes on classic dishes, on gritty Stock Island.
Louie鈥檚 Backyard, once the playground of Jimmy Buffett and Hunter S. Thompson, is a gourmet restaurant known for its shrimp and grits, conch and other dishes, with ocean views and an outdoor bar.
Take a six-minute ferry ride to the private island Sunset Key for breakfast overlooking the beach at Latitudes, which is open to the public.
WHERE TO STAY
La Concha Key West (starting at $249 in summer and fall, $699 in winter and spring) has an ideal location on Duval Street and recently had a $41 million renovation. There鈥檚 free rum punch in the lobby at happy hour and free mojito tastings daily at 4:30 in Tropicado, the hotel鈥檚 bar.
The Pier House Resort & Spa (from $359 in low season, $749 in high season) has a terrific location off Mallory Square and is the only beachfront hotel on the gulf side of the island. Jimmy Buffett got his start playing for Heinekens in 1971 at the hotel鈥檚 atmospheric Chart Room Bar.
The Perry Hotel & Marina (from $189 in low season, $350 in high season), on Stock Island, has stylish nautically themed rooms, some overlooking the marina, that are a good value.
Vacation rentals aren鈥檛 cheap, with an average nightly rate of $628, according to AirDNA. Properties in Old Town and those with pools or water views will be pricier. For slightly less expensive properties, look on nearby Stock Island.
This article originally appeared in . 漏 2025 The New York Times
