Old Town Key West is built for wandering on foot or by bike — porch-lined lanes, a chaotic party street, and a working harbor at sunset.
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.
Tips for Squares & Streets
- Arrive at Mallory Square 45-60 minutes before official sunset for a spot at the rail.
- Rent a bike or scooter — Old Town is small but the heat makes long walks tiring.