Key West sits 128 miles south of Miami at the end of US-1, the southernmost city in the continental United States. Old Town's 3,000 preserved Victorian conch houses are the most intact 19th-century neighborhood in Florida — all walkable, most free to see from the street. The city is 4 miles long and 2 miles wide, so two days covers the Historic District, the nightly sunset at Mallory Square, and a morning at Blue Heaven without needing a car.
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Historic District
Key West Historic District & Duval Street Must-see
Monroe County · Key West
The Key West Historic District covers Old Town — roughly the area north of Truman Avenue and west of White Street — and contains over 3,000 preserved Victorian-era conch houses, the most complete collection of 19th-century wood-frame structures in the US. Duval Street runs 1 mile from the Atlantic Ocean on the east to the Gulf of Mexico on the west, making it one of the only streets in the continental US that spans two coasts. The architecture dates from the 1880s and 1890s when Key West was the wealthiest city in Florida, built on sponging, cigar manufacturing, and salvage from shipwrecks.
Mallory Square, at the western end of Duval, hosts the Sunset Celebration every evening starting 90 minutes before sunset — street performers, artisan vendors, and crowds gather on the waterfront to watch the sun drop over the Gulf. Entry is free and the celebration runs year-round. From Duval, the Southernmost Point buoy — the closest you can legally stand to Cuba in the US, at 90 miles — is a 10-minute walk south on Whitehead Street. The entire district is walkable; plan 3–5 hours to explore properly on foot.
Dining
Blue Heaven (Key West) Must-see
Monroe County · Key West
Blue Heaven is at 729 Thomas Street in the Bahama Village neighborhood, 0.4 miles west of Duval Street. The restaurant occupies an outdoor courtyard on the site that Ernest Hemingway used as a boxing ring in the 1930s — resident roosters, cats, and mango trees that have been part of the property for decades share the dining space with guests. The menu runs all day: banana foster pancakes and lobster Benedict at brunch, conch fritters and grilled fish at lunch, and Key West pink shrimp at dinner.
Blue Heaven does not accept reservations — seating is walk-in only. Weekend brunch draws a 45-minute wait by 10am; arriving when the restaurant opens at 8am avoids the queue entirely. Weekday lunches have significantly shorter waits. Bahama Village is a 10-minute walk from the Duval Street strip through a residential neighborhood of painted conch cottages.
Planning Notes
Where to stay: Old Town hotels on or near Duval Street put you walking distance from the Historic District and Mallory Square. Budget options cluster on the eastern side of Old Town near White Street; boutique properties occupy quieter side streets off Duval. For Atlantic beach access, the Casa Marina and Southernmost Beach Resort are 1.5 miles south of Old Town.
Book ahead: Blue Heaven does not take reservations — arrive by 8am on weekends or plan for a 45-minute wait. The Historic District and Mallory Square require no advance booking. Fort Zachary Taylor State Park (not in this guide) charges a vehicle entrance fee and can fill on peak weekends — arrive before 10am.
Getting around: Key West is 4 miles long and completely flat — bicycle rentals are the standard way to cover the island. Old Town is walkable for the core sights. Parking in Old Town is scarce and metered; the free park-and-ride lot on US-1 near College Road runs a shuttle into downtown.
