United States

Key West

Roosters crossing the street while the entire island gathers to applaud the sunset.

#Water#Solo#Couple#Family#Friends#Relaxed#Culture#Historic#Unique

Key West smells of salt, frangipani, and frying conch — a scent that hits you the moment you step off the Overseas Highway and onto an island where roosters have the right of way. The whole town gathers at Mallory Square each evening to applaud the sunset, a ritual so ingrained that street performers time their acts to the angle of the light. The pace here is not slow so much as deliberately indifferent to whatever pace exists on the mainland.

Key West is the southernmost point of the continental United States, closer to Havana than to Miami, and its culture reflects that proximity. The island's architecture — Caribbean shotgun houses, Victorian gingerbread cottages, Bahamian clapboard — tells the story of wreckers, cigar makers, and shrimp fishermen who built the place before the highway connected it to the rest of Florida in 1938. Ernest Hemingway wrote 'To Have and Have Not' and parts of 'For Whom the Bell Tolls' in his house on Whitehead Street, where six-toed cats — descendants of his own — still roam the garden. Duval Street runs the full width of the island in barely eight blocks and contains the highest concentration of bars per metre of any street in America. The Key West Literary Seminar draws writers from across the country each January, and the city claims more published authors per capita than any other American city its size.

24.555° N · 81.782° W

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Best For

Couple

Sunset from Mallory Square, key lime pie split on a dock, and the kind of unhurried warmth that makes you forget which day of the week it is — Key West does low-key romance better than anywhere else in Florida.

Friends

Duval Street's density of bars, the snorkelling trips to the reef, and the general sense that rules are optional make Key West the kind of place where group trips acquire stories that get retold for years.

Solo

Hemingway came here to write alone, and the island still rewards solitude — a borrowed bicycle, a book, a bar stool, and a sunset that no one owns.

Family

Snorkelling, sunset celebration, Dry Tortugas day trip, Butterfly Conservatory

Why This Place

Mallory Square's nightly Sunset Celebration has drawn street performers and crowds since the 1960s — the applause begins the moment the sun touches the horizon.
Wild six-toed cats, descendants of Ernest Hemingway's pets, still roam the garden of his house on Whitehead Street alongside tourists and paying visitors.
Duval Street runs the full width of the island in barely eight blocks and contains the highest concentration of bars per metre of any street in America.
The Key West Literary Seminar draws writers from across the country each January — the city has more published authors per capita than any other American city its size.