Keys to Key West: Three Days Down the Overseas Highway

For the relaxed version: skip the organized boat tours and instead rent a kayak for a slow paddle through the park's mangrove trails, or wade in at Cannon Beach with rented snorkel gear and float above the sandy bottom watching the fish. The 30,000-gallon aquarium in the visitor center is a good air-conditioned option in summer. The park's picnic area under the palms is ideal for a late morning coffee with a view of the lagoon.

A dark, authentic Keys dive bar at MM 104 on Florida Bay — scenes from the 1948 Bogart and Bacall film Key Largo were shot here, and 78 years later the bar has not noticeably changed in character. Cold beer, plastic chairs, local regulars, and a sunset deck over the bay. This is the correct way to spend a Keys afternoon.

Start the Islamorada day at Robbie's: feed the giant tarpon from the dock ($3 admission + $4 baitfish), then rent a kayak or paddleboard for a slow Florida Bay paddle in the shallow backcountry behind the marina. Robbie's also has the best access to kayak rentals for the Indian Key backcountry channel.

The best free public beach in the Upper Keys — a mangrove boardwalk trail leading to a shallow Atlantic beach, warm clear water, and the kind of uncrowded, no-concession morning that the Keys still offer if you know where to find it.

Walk out on the old Seven Mile Bridge (the 1912 Flagler railroad bridge, now closed to cars and open as a pedestrian path) at sunset: two miles of open Atlantic to the south, Florida Bay to the north, and a sky that takes up 80% of the view. One of the most expansive sunset vantage points in the Keys.

Ernest Hemingway lived in this Spanish Colonial house on Whitehead Street from 1931 to 1939 — his most productive period, during which he wrote A Farewell to Arms, For Whom the Bell Tolls, To Have and Have Not (set partly in Key West), Death in the Afternoon, and The Snows of Kilimanjaro. The house, built in 1851, was given to him by his father-in-law and remains furnished largely as it was in Hemingway's time. Its most famous residents are now the 44 six-toed (polydactyl) cats descended from a six-toed cat Hemingway received from a ship's captain; they are free to roam the house and grounds. Guided tours run continuously and are remarkably good — the guides include detailed literary context alongside the house history. The pool, installed at great expense in 1938, was the first private swimming pool in Key West.

Duval Street is Key West's main artery — 1.3 miles from the Gulf to the Atlantic — lined with bars, restaurants, and shops in a mix of Victorian wooden buildings, Conch (island vernacular) architecture, and tropical storefronts. Walk the full length at a slow pace. The Southernmost Point buoy marker at the corner of Whitehead and South streets is the most photographed landmark in Key West: a red, yellow, and black concrete buoy marking 90 miles to Cuba, with a permanent queue of tourists for photos. The Fort Zachary Taylor beach, a 10-minute walk west, has the best swimming in Key West.

Mallory Square's nightly Sunset Celebration has been a Key West institution since the 1960s, when the hippie counterculture gathered on the waterfront to watch the sun go down and the tradition calcified into something the whole city observes. Street performers — acrobats, trained cats, fire eaters, jugglers, magicians — set up around the square in the hour before sunset; a spontaneous crowd gathers; and when the sun touches the Gulf horizon, the crowd applauds. The kitsch is self-aware and the sunset is genuine. It is the most Key West thing in Key West.