Top 14 Must-See Attractions in Key West

The single most photographed object in Key West — a concrete buoy marking the southernmost point in the continental United States, just 90 miles from Cuba. Expect a line for photos any time after 9am.

The Spanish Colonial house where Hemingway wrote A Farewell to Arms and To Have and Have Not, now home to dozens of polydactyl six-toed cats descended from his original pet, Snow White.

A Civil War-era fort turned state park with the best beach in Key West at its doorstep. Snorkel the rocky shoreline, then tour original cannon batteries under moss-draped trees.

The main artery of Key West, running ocean to gulf — bars, drag shows, T-shirt shops, and live music by night; galleries and cafés by day. Loud, campy, and unmissable.

The harbor-front plaza where the entire town gathers every evening for the Sunset Celebration — street performers, artisan stalls, and a genuinely spectacular horizon over the Gulf.

Multiple tall ships (like the Western Union and America 2.0) depart from the harbor nightly for a two-hour sunset cruise with drinks included — the classic Key West evening.

Catamaran trips out to the only living coral barrier reef in the continental US, part of the Florida Keys National Marine Sanctuary — gear, instruction, and usually a rum punch included.

A Key West institution since the 1930s, this legendary bar was once a favorite haunt of Ernest Hemingway and remains one of the liveliest spots on the island. Expect live bands playing rock, country, and island tunes almost every night, a boisterous crowd of locals and visitors, and walls covered in memorabilia from decades of history. The frozen drinks and conch fritters keep people fueled well past midnight. Arrive early on weekends to snag a table near the stage, as the bar fills up fast once the music starts. It is loud, unpretentious, and quintessentially Key West, a must for anyone wanting to feel the pulse of the islands famous bar-hopping culture.

Tucked beside Mallory Square, this historic open-air aquarium has been introducing kids to marine life since the 1930s, long before Florida built its bigger theme-park tanks. Guides run hands-on touch-tank sessions where children can carefully handle horseshoe crabs, sea stars, and small nurse sharks, and the shark-feeding demonstration is a reliable crowd-pleaser for younger visitors who want to see something with teeth up close. Exhibits cover local Keys species like tarpon, sea turtles, and stingrays in tanks sized for eye-level viewing rather than towering displays, which keeps toddlers engaged without the overwhelm of a larger facility. The whole visit runs about an hour, making it easy to slot in between beach time or a walk down Duval Street. Indoor and shaded outdoor sections offer a break from the midday sun, and the gift shop leans into ocean-themed souvenirs kids actually want.

Held each spring, the Key West Songwriters Festival returns May 6 to 10, 2026, filling Duval Street bars and intimate venues with the writers behind some of country and pop music's biggest hits. Unlike a typical concert, this festival is built around in-the-round performances where three or four songwriters trade songs and stories on the same small stage, often previewing unreleased material. Venues like Irish Kevin's, The Bull, and the Hard Rock Cafe host free daytime sets, while evening showcases at bigger rooms sometimes carry a cover charge. It is a favorite for music lovers who want an up-close, unplugged experience rather than a stadium show. Expect the island to feel especially lively, with locals and repeat visitors treating it as an unofficial kickoff to the warmer season. Comfortable shoes help since most people bar-hop between multiple sets in a single evening.

Key West's biggest annual event, Fantasy Fest, takes over the island from October 23 to November 1, 2026, ten days of costume parties, themed parades, and elaborate body-painted street processions. What began decades ago as a way to boost off-season tourism has grown into a Mardi-Gras-style spectacle, with a different costume theme announced each year and a headline parade down Duval Street that draws enormous crowds. Daytime hours bring family-friendly pet costume contests and a children's parade, while nights turn distinctly adult, especially along the famous Duval Street strip. Accommodation across the island sells out months in advance, and prices rise accordingly. Visitors who prefer a quieter trip may want to avoid this window entirely, while costume enthusiasts consider it a bucket-list event. Either way, it is the clearest example of Key West's anything-goes personality on full display.

On December 31, 2026, Key West closes out the year with three simultaneous countdowns that only this island could pull off: a giant conch shell lowered at Sunset Pier, a red high-heel shoe drop featuring a drag performer outside Bourbon Street Pub, and a pirate wench descending from the mast of a tall ship at the Historic Seaport. Crowds move between Mallory Square and the waterfront bars throughout the evening, with live music, fireworks over the harbor, and street performers adding to the carnival atmosphere. It is a distinctly local twist on a globally familiar night, blending the theatrical flair of Duval Street with the maritime setting that defines the island. Arriving early to claim a spot near the water is worthwhile, as the Historic Seaport and Mallory Square both fill up well before midnight. Warm clothing is rarely needed given Key West's mild winter nights.

Hidden behind an unmarked gate near Simonton Street, this dense botanical hideaway feels nothing like the manicured gardens elsewhere on the island. Founded decades ago by a naturalist and artist, it is planted almost entirely with native and rare tropical species, sheltering resident macaws and free-roaming cats among the ferns and towering bamboo. There are no gift shops or crowds here, just a shaded, humid tangle of paths that make Duval Street feel a world away. Entry is by small donation, and visitors often have the place nearly to themselves. It is best appreciated slowly, camera in hand, as an antidote to the island's louder attractions and a genuine local secret many residents still do not know exists.

Every early December, the Historic Seaport at Key West Bight fills with locals and visitors for the island's answer to a Christmas market crowd: a harbor lined with food and drink vendors watching decorated boats cruise past strung with lights, tinsel, and inflatable Santas lashed to the rigging. It is a distinctly Key West mash-up of nautical tradition and holiday kitsch, with sailboats, shrimp boats, and charter catamarans all competing for the best-lit-vessel title. Arrive early to grab a spot along the Bight boardwalk or a table at one of the seaport bars, since the route fills in fast. Expect live music, seasonal cocktails, and a genuinely festive, unpretentious atmosphere. Free to watch from the public waterfront, though restaurants and bars along the route get busy and may add a cover or minimum.