Key West sits at the southern tip of the Overseas Highway, roughly a three-and-a-half-hour drive southwest of Miami. The island is known for its nineteenth-century timber cottages, shallow reef diving, and deep Cuban culinary roots. The flat streets are best explored entirely by bicycle. Key West is worth visiting if you want to eat wild pink shrimp at the docks, study Bahamian frame carpentry, and snorkel shallow patch reefs.
Last updated 14 Sept 2026
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Key West compresses into a compact, bike-friendly four square miles where daily life pivots around the salt water and the shade. Old Town contains the bulk of the historic wooden architecture, while the Historic Seaport handles charter boats, fish houses, and dock repairs. It suits independent travellers who prefer walking flat lanes, eating fresh catch in open-air sheds, and avoiding structured schedules.
Rent a single-speed bicycle by 8:00 to tour Whitehead and Eaton streets before the heat builds. Grab a pressed Cuban sandwich on Petronia Street for lunch. Spend the afternoon at Fort Zachary Taylor's shaded pine beach, then finish with whole fried snapper by the docks as fishing skiffs tie up. Select 1 Day above to see it.
Spend morning exploring Bahama Village, stopping for café con leche and warm pan cubano. Cycle east along South Roosevelt Boulevard to Higgs Beach and the West Martello civil war fort, then cross over to Stock Island for smoked amberjack dip and local craft beer away from Old Town crowds. Choose 2 Days to expand the plan.
Board the 8:00 ferry out to Garden Key in Dry Tortugas National Park to explore the massive brick casemates of Fort Jefferson and snorkel untouched coral ledges. Back on Key West, spend a slow late afternoon wandering through the overgrown lanes of Key West Cemetery.
Order Key West pink shrimp steamed in Old Bay, cracked conch fritters, and whole yellowtail snapper fried crisp with yellow rice and black beans.
Walk Old Town to see 1800s Conch houses, metal-roofed cigar cottages, gingerbread fretwork, and the maritime ship-salvage mansions along Eaton Street.
Drink café con leche at Sandy's window and order roast pork with mojo, fried plantains, and pressed Cuban bread in Bahama Village.
Inspect wrecking salvage maps, salvaged Spanish galleon silver at the Mel Fisher Museum, and the 1825 Key West Lighthouse on Whitehead Street.
Stroll the Atlantic promenade along South Roosevelt Boulevard toward Higgs Beach, passing the historic West Martello civil war tower.
Board morning catamarans to the Florida Reef tract for shallow patch reef drifts among brain coral, parrotfish, and sea turtles.
Pick up fresh stone crab claws, Key limes, and smoked fish spread from seafood shacks and fishmongers along the historic seaport docks.
Walk the 1847 Key West Cemetery to read marble headstones, maritime epitaphs, and nineteenth-century cigar-maker memorials.
Explore shady brick pathways bordered by tropical palms, native orchids, and heavy banyan trees at the Key West Garden Club.
Catch the morning ferry to Dry Tortugas National Park to explore massive brick-walled Fort Jefferson and snorkel pristine moat walls.
Compare tart, pale custard Key lime pies made with real egg yolks and graham cracker crusts at classic bakeries along Thomas Street.
Paddle a rented kayak through shallow tidal creeks and mangrove tunnels off Stock Island to spot nurse sharks and wading herons.