Key West Travel Guide

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.

Built in 1848 and still standing 88 feet tall across the street from the Hemingway House. Climb the 88 steps for a 360-degree view over Old Town's tin roofs and the surrounding sea.

A massive 19th-century brick fortress rising from a remote island 70 miles west of Key West, reachable only by ferry or seaplane. Surrounded by some of the clearest snorkeling water in Florida.

Gold bars, emeralds, and silver coins recovered from the 1622 wreck of the Nuestra Señora de Atocha, one of the richest shipwreck salvages in history, displayed a few blocks from where it was found.

An 1891 red-brick Custom House packed with exhibits on wreckers, cigar rollers, and Cuban immigration that shaped the city, plus rotating contemporary art shows.

A theatrical, actor-led walk through the city's 19th-century wrecking industry, when salvaging sunken ships made Key West the richest city per capita in the United States.

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.

A historic Afro-Bahamian neighborhood west of Duval Street with narrow lanes, roosters wandering underfoot, and some of the city's most laid-back local eateries away from the tourist strip.

A glass-enclosed tropical habitat with hundreds of free-flying butterflies, flamingos, and a waterfall, right in the middle of Old Town — a favorite with families.

Ruins of a Civil War-era fort reclaimed by a lush tropical garden of orchids and native plants, with ocean views over Higgs Beach and far fewer crowds than the main sights.

The longest beach in Key West, with a wide stretch of sand, watersports rentals (parasailing, jet skis, paddleboards), and plenty of room to spread out.

A calmer, more local beach with a fishing pier, picnic pavilions, and the sobering African Cemetery at Higgs Beach memorial nearby, marking the graves of rescued Africans from 1860 slave ships.

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 90-minute narrated tram loop past all of Old Town's major sights — a good first-hour orientation before deciding what to revisit on foot.

Guided light-tackle fishing trips into the shallow flats around Key West for tarpon, bonefish, and permit — a bucket-list trip for anglers, no experience required.

Drive the iconic Seven Mile Bridge north to Bahia Honda, widely considered the best beach in the Keys, with turquoise water and views of the old railroad bridge.

The self-proclaimed "Sportfishing Capital of the World," about 75 minutes north, with the History of Diving Museum and excellent seafood shacks along US-1.

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.

Right in the heart of the entertainment strip, this rowdy pub is known for solo acoustic performers who keep the crowd singing along late into the night. Expect a packed dance floor most evenings, cold beer, and a party atmosphere that spills out onto the sidewalk. The energy here is high-volume and high-fun, making it a favorite stop for bachelor and bachelorette groups touring the strip. There is no cover charge, so visitors can pop in for one song or stay for hours. Bartenders pour generously and the crowd tends to be friendly and easygoing. It is a reliable choice for anyone looking for a classic, unfiltered slice of the islands nightlife without a reservation or dress code.

A weathered, unpretentious neighborhood dive dating back over a century, the Green Parrot is beloved by locals as the anti-tourist-trap bar just off the main strip. Its open-air windows, ceiling fans, and eclectic decor set the scene for blues, funk, and reggae acts that play several nights a week. There is no glitz here, just cold drinks, a friendly crowd, and genuinely good live music without the crush of the busier strip bars. Regulars trade stories at the bar while a mixed-age crowd sways along to the band. It captures an older, grittier version of Key West that still exists a few blocks off Duval Street, appealing to travelers who want nightlife with more character and less spectacle.

Accessible only by a short ferry ride to Sunset Key, this waterfront lounge offers a quieter, more upscale alternative to the raucous downtown scene. Guests sip craft cocktails on the sand as the sun dips below the horizon, with soft island music playing in the background. The setting is intimate and romantic, popular with couples celebrating anniversaries or simply looking to escape the crowds. Food service ranges from light bites to full dinner, so an evening here can easily stretch into a leisurely night out. The ferry transfer adds a small sense of adventure and exclusivity. It is an ideal pick for travelers who want a memorable evening view paired with a calmer, more polished nightlife experience.

Perched atop a building along the entertainment strip, this open-air rooftop bar has a laid-back, clothing-optional reputation that has made it a quirky local legend. Beyond the novelty, it offers sweeping views over the streets below, a relaxed tropical vibe, and a solid drink menu perfect for unwinding after a day of sightseeing. Live DJs or acoustic sets sometimes play in the evenings, adding to the breezy, anything-goes atmosphere. It draws an eclectic mix of free spirits and curious first-timers. The rooftop setting makes it a great spot to watch the energy of the street below while enjoying a cocktail above the noise, offering a different angle on the citys after-dark scene.

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.

This sprawling waterfront green space on the site of the old naval station gives kids room to actually run, something in short supply on Key West's narrow historic streets. A splash pad cools things down on hot afternoons, a modern playground covers climbing and swinging, and a skate park and basketball courts keep older children occupied while parents relax on the open lawn. The park also hosts an amphitheater where free community events and concerts pop up throughout the year, so it is worth checking the schedule before a visit in case there is live entertainment to catch. Wide waterfront paths are ideal for scooters or a family bike ride, with views out toward the harbor and passing cruise ships. Unlike the paid attractions clustered around Duval Street, this is free to enter and shaded by mature trees, making it a natural stop to burn off energy before or after a day of sightseeing.

For families with children too young or too nervous for snorkeling, a glass-bottom boat cruise out to the coral reef is the easiest way to see Florida's underwater world without anyone getting wet. Large viewing panels built into the hull let kids press their faces against the glass and watch parrotfish, sergeant majors, and coral formations glide by while a naturalist narrates what is visible below. Trips typically run a couple of hours round-trip from the marina near Mallory Square, with shaded seating and an upper deck for catching the breeze. It is a gentler alternative to the reef snorkeling trips also popular in Key West, and works well for toddlers, grandparents, or anyone prone to seasickness who still wants reef views. Many operators time the return so passengers catch part of the sunset over the water. Snacks and drinks are usually available on board, and the boats are stable enough that motion sickness is rarely an issue.

A neighborhood favorite away from the tourist crowds, Bayview Park pairs a shaded playground with a splash pad that runs during the warmer months, giving younger kids a low-key place to cool off between sightseeing stops. The park sits under a canopy of large trees, including century-old specimens that provide welcome relief from the Florida sun, and there are picnic tables and open lawn for a packed lunch. A public pool adjoins the park for swimming lessons or lap time, and the adjacent dog park and tennis courts mean there is usually something happening for every member of the family. It is far less polished than the attractions closer to Duval Street, but that is part of the appeal: local families use it as their everyday park, so kids get a chance to play alongside Key West residents rather than only other tourists. Parking is easy and free, a rarity in the historic district.

Hidden behind an unmarked gate just off Simonton Street, this lush tropical garden feels like stepping into a jungle in miniature, with towering palms, orchids, and free-roaming parrots that make it feel more like an adventure than a formal botanical stop. Kids tend to love the sense of discovery, following narrow paths between dense plantings while colorful macaws call out overhead, and there is no rush to move quickly through since the whole space can be explored at a toddler's pace. It is quieter and less crowded than the bigger name attractions nearby, which makes it a good option for a mid-afternoon breather when children need a change of pace from beaches and museums. The garden is compact enough to see in under an hour but full of small details, insects, lizards, hidden sculptures, that reward slow exploration. Comfortable shoes are recommended since paths can be uneven and shaded rather than paved.

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.

Every June, the island turns into one of Florida's most colorful celebrations as Key West Pride takes over downtown from June 4 to 8, 2026. The week combines a beach party at Fort Zachary Taylor, drag brunches, a sunset tea dance, and a rainbow-lit street festival along Duval Street, capped by a Saturday parade that draws thousands of spectators. Key West has long been a haven for LGBTQ+ travelers, and Pride week is when that history is celebrated most visibly, with rainbow flags hanging from nearly every guesthouse and bar. Many of the events are free and family-friendly during the day, shifting to an adults-only party atmosphere after dark. Hotel rooms book up quickly for this week, so early reservations are strongly recommended. It is a joyful, high-energy way to experience the island's famously inclusive spirit.

Timed around Ernest Hemingway's July birthday, Hemingway Days runs July 15 to 19, 2026, and is best known for its raucous Papa Hemingway Look-Alike Contest at Sloppy Joe's Bar, where dozens of bearded men in fishing vests compete for the title. Beyond the contest, the week includes a short story writing competition, a marlin fishing tournament, and readings that celebrate Hemingway's decade living on the island. The event captures Key West's playful, literary side and its enduring fascination with its most famous former resident. Streets around the historic Old Town fill with visitors snapping photos alongside look-alikes, and several bars extend their happy hours to match the festive mood. It is equal parts literary tribute and beach-town party, which sums up Key West rather well. Arrive early for the look-alike contest since seating at Sloppy Joe's disappears fast.

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.

Tucked on Solares Hill, this 19th-century burial ground is one of the island's most atmospheric and least-visited attractions. Above-ground vaults and wind-worn headstones reflect Key West's Bahamian, Cuban, and naval heritage, but the real draw is the dry local humor carved into the marble. Look for the infamous epitaph reading I Told You I Was Sick, alongside monuments to sponge divers, sailors, and yellow fever victims. Free self-guided maps are available at the Sexton office near the Margaret Street entrance, or join a low-key walking tour led by longtime residents. Shaded by gumbo-limbo and frangipani trees, it is a peaceful, strange, and strangely moving detour that most cruise-ship visitors never discover.

Overshadowed by its more famous sibling near the beaches, this Civil War-era brick fortress near the airport draws far fewer visitors despite its strange charm. Inside the vaulted casemates, exhibits cover shipwrecks, Cuban refugee rafts, and local folk art, but the star attraction is Robert the Doll, a supposedly haunted 1906 toy said to curse anyone who photographs him without permission. Climb the spiral watchtower for a breezy view over the salt ponds and airport runway, quite different from the postcard sunsets downtown. Because it sits outside the main tourist loop, the fort stays uncrowded even in high season, making it an easy, offbeat stop for history buffs and curious skeptics alike.

Florida's southernmost botanical garden sits on a quiet freshwater wetland far from the harbor bustle, preserving native hardwood hammock that once covered much of the island. Volunteer-run and rarely crowded, its shaded boardwalks pass butterfly-friendly plantings, a native tree collection, and a small memorial garden honoring islanders. Unlike the manicured tropical stops downtown, this 28-acre reserve feels genuinely wild, with gumbo-limbo, mahogany, and orchids growing as they would have centuries ago. Birdwatchers come early for migratory songbirds, while others simply enjoy the rare quiet. A small nominal admission supports ongoing habitat restoration, and the modest visitor center offers context on the island's vanishing native ecosystem that few tourists ever learn about.

While tour buses funnel everyone toward Mallory Square, locals quietly gather at this unassuming pier near the Truman Annex for the same sunset without the crowds, street performers, or souvenir carts. It doubles as a favorite spot for shore fishing and casual swimming off a small ladder into the harbor, with benches facing west toward the open water and passing sailboats. There are no vendors or ticket booths, just a stretch of open concrete where residents walk dogs, toss fishing lines, and watch the same colors spread across the sky that draw thousands elsewhere. Bring a drink, arrive an hour before dusk, and claim a spot on the seawall for one of the island's best-kept evening rituals.

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.

Key West's largest public park becomes the closest thing the island has to a holiday market during December, with a lit community Christmas tree, seasonal food trucks, and periodic weekend events pulling in families from all over the Keys. The open lawns and amphitheater host live music and craft or food vendors on select evenings throughout the month, giving visitors a casual, outdoor gathering spot rather than a formal market. Check the park's event calendar before visiting, since vendor nights and concerts rotate rather than running daily. The waterfront setting means sunset views over the harbor while string lights come on, and there is plenty of open space for kids to run around. Free entry to the park itself; individual food and drink vendors charge separately.

Each December the Ernest Hemingway Home and Museum decorates its towering Norfolk Island pine into one of the island's most photographed Christmas trees, wrapped in lights beside the writer's 1851 Spanish Colonial house. Visitors touring the museum's famous six-toed cats and Hemingway's writing studio get a bonus dose of holiday atmosphere in the tropical garden setting, a striking contrast to typical snowy Christmas-tree scenes. Regular museum admission applies and includes the guided house tour along with the seasonal decor, so it works well as a combined sightseeing and holiday-photo stop. Go in late afternoon for softer light on the tree and garden. The tree typically stays lit throughout December into early January, well past most mainland displays have come down.

Duval Street's shops, guesthouses, and bars lean into palm-tree Christmas lights, wreaths on gingerbread-trim porches, and seasonal cocktail menus throughout December, turning an evening stroll into an easy substitute for a market crawl. Rather than stalls selling mulled wine, expect open-air bars serving rum-spiked eggnog and seasonal drink specials, plus shop windows dressed up for the season. Walk the street after sunset when the lights and string bulbs on balconies and storefronts really stand out. It pairs naturally with dinner reservations along the strip or a stop at Mallory Square, a few blocks away, for the nightly sunset celebration with local performers and craft vendors. No cost to walk and browse; individual bars and shops set their own prices.