7:30 a.m. Fill up on Cuban cuisine
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.
9 a.m. Meet Hemingway’s cats
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.
10 a.m. Go fishing
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.
3:30 p.m. Learn some booty tales
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.
4:30 p.m. Check out the 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 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.
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 “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.
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 “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.