Closer to Cuba than Miami, this tiny island (only two by four miles!) has long been a haven for writers -- including Ernest Hemingway, Tennessee Williams, and Robert Frost -- artists, treasure hunters, and fun seekers. Its mix of creative and eccentric characters -- and the carefree attitude of natives who live year-round on Key West, the southernmost point in the continental United States -- make the self-titled "Conch Republic" anything but your average island getaway.
In a Word: Conch
This is the area's patron mollusk. Some facts: It's pronounced "konk" -- mispronouncing it is a dead giveaway to "Conchs" (as Key West locals refer to themselves) that you're a mainlander. It's used for fritters and devilishly delicious chowder -- a bite of tart key lime pie will salve your taste buds after one too many spicy sips.
- Ernest Hemingway: The spirit of legendary Papa Hemingway dominates the imagination -- and souvenir shops -- of Key West. Between 1928 and 1939, Hemingway wrote For Whom the Bell Tolls and The Snows of Kilimanjaro from his Spanish colonial villa near the main drag. Drink where he drank at Captain Tony's Saloon, and eat where he sparred at Blue Heaven Restaurant. His house is now a museum -- and home to more than 50 cats, many of them six-toed, all of whom seem to be descendants of Hemingway's original brood. Hit the Hemingway Days Festival in July for Papa H lookalike contests and fiction competitions.
- Bike sights: Hop a two-wheeler to circle the island and explore quiet side streets at your leisure. To learn about the island's history, native flora and/or fauna, join a guided bike tour.
- "Conch" houses: Pockets of prosperity -- and austerity -- in Key West have left the historic district with a melange of architectural styles (collectively called "conch architecture") dating back to the early 1800s and unified by swirly gingerbread trim. The main styles include classic revival (gabled roofs, columned porches); eyebrow house (a style unique to Key West, with a roof that overhangs the top-floor windows to keep the sun out); Bahamian (wraparound porches and floor-to-ceiling windows to best ventilate its interior); Queen Anne (lavish details, a pointed turret); and shotgun (small single-story houses also known as cigarmakers' cottages).
- Blazing sunsets: Transition into starry evenings with the nightly carnival-like sunset celebration at Mallory Square, where mimes, jugglers, and fire-eaters try to steal the spotlight. Get there early to grab a good spot along the water and people-watch.
- Duval Street: Stroll this main street and browse the little shops, galleries, and restaurants that sit cheek-to-jowl along its narrow sidewalks. At night, do the "Duval Crawl" between bars and hot spots for a high concentration of rum-fueled fun.
Best Place to Kiss
The restaurant and bar Louie's Backyard is an institution on Key West, partly because of its multitiered dining deck that overlooks the ocean and partly because Jimmy Buffet allegedly penned "Margaritaville" while sitting in the front-porch swing. Need we say more?
When to Go
- Best weather: Winter, although temperatures hover between 73 and 82 year-round
- Best prices: Summer and fall
- Festival highlights: Old Island Days, from January to May, celebrates Key West's eclectic history; the 10-day Conch Republic Independence Celebration begins April 23 and features a parade, sea battles, and a drag-queen race; the annual Underwater Music Festival, in July, entertains fish and people with reggae, new age, and jazz; the 10-day Fantasy Fest in late October swirls with costume balls and a parade; and the Cuban-American Heritage Festival in early November celebrates all things cubano.
- Tying the Knot: Marriage License Requirements
See More: USA + Canada