The city that was once home to pirates and cigarmakers eventually gave way to lost souls looking to get away from it all ... indefinitely.
Key West was at one time the country's richest town (salvaging wrecks had its perks), and always has been its southernmost. It's been a haven for hippies, fishermen, writers, spring breakers and the gay and lesbian community.
But Key West isn't the booze-soaked party town of decades past. Beyond the saloons filled with guitar-strumming revelers singing odes to their favorite beverages are serene and chic locales popular with families, singles and couples. Whether you're a cruise ship passenger, an international visitor or a Floridian on a quick road trip, Key West offers art, culture, music, history and even butterflies.
Here's just 48 hours' worth.
If you arrive in Key West in the late afternoon, the first thing you want to do is catch a gorgeous sunset. This tiny island offers several spots to watch the sun come to rest. Among the favorites is Louie's Backyard, an oceanfront Victorian home renovated into a high-end restaurant and seaside bar deck. On the National Register of Historic Places, it offers the best unhindered view of the nightly show.
If you prefer to watch from above, then don't miss the view from The Top. The rooftop lounge at Crowne Plaza La Concha, 430 Duval St., is the highest building in Key West.
Head a few blocks north for bar room merriment, or head south just a few feet and you won't be able to resist stopping at Fast Buck Freddie's, a tropical department store with a distinctly Key West flavor. Think Pier One meets "tropical trash."
For dinner, try Santiago's Bodega, which serves more than 30 tapas, from delicious lentil soup to pinchos morunos, spicy pork skewers with apple-mango chutney.
Another great choice is Michael's Key West, fine dining that bills itself as "a steakhouse that treats seafood fairly." Zagat rated it one of the top three in the state and No. 1 in the Florida Keys. Ask for the "light" menu, which features less expensive half-sized portions.
Afterward, head to Virgilio's for a relaxed grown-up atmosphere in quaint courtyard surroundings. On Thursday nights, head there after 10 for live Latin music. Ladies, be ready to be invited to the dance floor by Key West elder salsa statesmen. (Trust us on this: Pace yourself on Virgilio's famed martinis.)
For your first morning, have breakfast at Pepe's Café, the "oldest eating house in the Florida Keys." It's been around for 100 years.
If you're visiting from frigid environs, you'll probably want to head to the beach. By now, you've figured out that you should be getting around on a bicycle, so rent one from the numerous vendors about town. Many deliver.
If you're single and under 30, head to Smathers Beach on South Roosevelt Boulevard and take in some volleyball or Frisbee.
The best swimming spot is Fort Zachary Taylor Historic State Park, built in the mid-1800s to defend the country's southeast coast. Located at the end of Southard Street on Truman Annex, this is where the water is clear and snorkeling is easy. Bring a pair of goofy swim shoes, as there are as many rocks as grains of sand.
For water sports, locals recommend Lazy Dog for paddleboarding and kayaking.
Have lunch right on the beach at Salute. For a meal overlooking the marina, try Alonzo's Oyster Bar, where half-price seafood appetizers make happy hour a standing-room-only affair.
Spend your afternoon strolling the city's funky cemetery, home of the "I told you I was sick" headstone. The 1847 graveyard is right in the middle of Old Town, where visitors are greeted by a memorial to the 1898 sinking of the USS Maine, a full-sized grave for a dwarf-sized military general and other quirky plots.
Guided tours are available at 9:30 a.m. Tuesdays and Thursdays through the Historic Florida Keys Foundation. Reservations are required. For more information, call 305-292-6718.
At this point, you should be ready for another sunset. And this time, forget what the local "conchs" say: You really can't leave Key West until you have seen the sun go down at Mallory Square, home of the nightly arts festival where the sun sets amid a backdrop of fire-eating Houdinis and street art vendors.
Stop at El Meson de Pepe's after the sunset to listen to the live salsa band. For a slice of old Key West, head to Schooner Wharf Bar. The locals' favorite is the Green Parrot, the kind of place where if you close your eyes, you can envision one-eyed pirates plotting a gold heist beside you.
On Sunday morning, have your first meal at Harpoon Harry's, 832 Caroline St., or at the more elegant Sarabeth's, 530 Simonton St.
Sundays make for a perfect museum day.
Among your most unusual choices, The Butterfly & Nature Conservatory, 1316 Duval St., allows you to walk among hundreds of winged creatures. Up to 60 species roam in the glass-enclosed habitat, delighting the children.
The restored Custom House, 281 Front St., offers glimpses into Key West's past through paintings and portraits. This year will feature an exhibit on Henry Flagler, the tycoon whose railroad put Key West on the map. The Audubon House, 205 Whitehead St., and the Oldest House, 322 Duval St., showcase historic Key West architecture. If you are more of a biography history buff, then the Hemingway House and the Little White House are good for anyone interested in author Ernest Hemingway or President Harry Truman, respectively.
No one's really too sure whether Hemingway's six-toed cat stories are true, but you can find plenty of felines roaming at 907 Whitehead St.
Cap your day at the White House Pier, 1400 Atlantic Blvd., for one last stroll under a setting orange sun. Don't forget your camera.
This story was first published on VISITFLORIDA.com.