Key West

Tour the Spanish Colonial mansion where Hemingway wrote some of his most celebrated novels, now famously populated by six-toed cats roaming the lush tropical grounds.

Gather at this iconic waterfront plaza each evening for the legendary Sunset Celebration, a nightly street-performer festival that transforms the harbor into an open-air spectacle.

This Civil War-era brick fortress sits at the island's southernmost tip and doubles as home to Key West's best natural beach, ideal for snorkeling the shallow reef just offshore.

The bold red, black, and yellow concrete buoy marking the continental USA's southernmost point is an unmissable photo landmark just 90 miles from Cuba.

Step inside a glass-enclosed tropical habitat where hundreds of live butterflies from around the world flutter freely past cascading waterfalls and rare flowering plants.

This crumbling Civil War-era fort tucked beside Higgs Beach has been lovingly reclaimed by the Key West Garden Club, filling its ruined ramparts with a secret jungle garden.

Climb the 88 steps of this 1848 lighthouse for a sweeping panoramic view of the island and browse the restored keeper's cottage filled with maritime artifacts below.

Key West's longest public beach stretches along South Roosevelt Boulevard, drawing locals at sunrise for calm shallow waters and beachside vendors renting kayaks and paddleboards.

Occupying a gorgeous wraparound porch at 915 Duval Street, this restaurant serves shareable small plates and inventive cocktails in an atmosphere that perfectly balances romance and revelry.

Set inside a beautifully restored Victorian inn, this intimate New American restaurant delivers flawlessly executed dishes like pan-seared local snapper with a wine list to match.

Perched directly over the Atlantic on a series of open-air decks, Louie's Backyard serves refined Caribbean-inspired cuisine with one of the most breathtaking oceanfront settings in the Keys.

This elegant but unfussy spot on Grinnell Street combines Mediterranean and Florida influences to produce standout dishes like stone crab claws with house-made aioli.

Key West's own craft brewery pours inventive small-batch ales and lagers steps from the Historic Seaport, with a breezy outdoor deck perfect for watching the marina traffic drift by.

Hemingway's legendary haunt on the corner of Duval and Greene has been pouring cold drafts and live music since 1933, making it an essential stop in any Key West crawl.

The oldest bar on the island, open since 1890, this beloved dive on Whitehead Street hosts live blues and rock most nights and draws an authentically local, no-nonsense crowd.

An open-air waterfront bar dockside at the Historic Seaport serving ice-cold Coronas and fresh fish dip while live bands play against a backdrop of bobbing sailing vessels.

A multi-level Duval Street complex housing several distinct bar environments under one roof, keeping the energy high until the early hours with DJs, pool tables, and an upstairs outdoor deck.

The beating neon heart of Key West nightlife, this mile-long strip links bar after bar, from drag shows to reggae clubs, earning its reputation as one of America's great party streets.

This spirited Duval Street institution hosts nightly drag performances that are equal parts hilarious and jaw-dropping, drawing a wildly diverse and enthusiastic crowd every night of the week.

Tucked down a quiet alley off Duval, this dimly lit martini lounge offers a sophisticated escape with live jazz, expertly crafted cocktails, and an intimate atmosphere unlike anywhere else on the island.