Florida Keys

The Florida Keys are an accident of geology — a 120-mile chain of low coral islands resting on an ancient coral reef that grew in a shallow tropical sea, then died and emerged as sea levels fell. The Overseas Highway, completed in 1938 on the raised bed of Henry Flagler’s Florida Keys railroad (largely destroyed by the 1935 Labor Day Hurricane), runs through this archipelago over 42 bridges spanning open water, culminating at Key West just 90 miles from Havana. It is one of the great American road trips, and the destination at the end of it is genuinely unlike anywhere else in the continental United States.

The Keys offer accommodation archetypes unavailable almost anywhere else in the continental US. Old Key West guesthouses — many converted from the 19th-century homes of sponge fishermen, cigar factory workers, and sea captains — offer intimately scaled lodging in a neighborhood of Bahamian vernacular architecture with deep porches and ceiling fans. Mile Marker Zero marks Key West’s southern tip, where the southernmost point in the continental US produces a social media queue at all hours. In the Upper Keys near Islamorada, waterfront fishing lodges with private boat slips have hosted serious anglers since Zane Grey fished here in the 1930s. Tiny resort islands accessible only by boat provide a level of Caribbean-adjacent tropical seclusion that would otherwise require a transatlantic flight.

The Florida Keys National Marine Sanctuary encompasses 2,900 square miles of ocean and protects the most extensive coral reef system in North America — the only living coral barrier reef in the continental United States. John Pennekamp Coral Reef State Park in Key Largo is the entry point: glass-bottom boat tours, snorkel trips, and scuba diving from shore or by guided boat into reef systems that support 650 species of fish. The Key Largo dry rocks, including the famous Christ of the Abyss bronze statue at 25 feet, are among the most accessible and photogenic reef dive sites in the world. Visibility regularly exceeds 60 feet in winter.

Key West is the Keys’ cultural and commercial center, a city of 25,000 that has been successively home to Native Calusa, Spanish colonizers, Bahamian Conchs, Cuban cigar workers, sponge fishermen, Navy personnel, writers (Hemingway spent a decade here), and the LGBTQ+ community that has been central to its character since the 1970s. The Old Town historic district is a UNESCO potential World Heritage Site; the architecture — Bahamian vernacular, Victorian, and early 20th-century frame construction — has been remarkably well preserved. Mallory Square’s nightly sunset celebration, a community gathering around street performers that has been happening since the 1960s, is one of America’s best free daily events.

Seventy miles west of Key West, accessible only by daily ferry or seaplane, Dry Tortugas National Park encompasses seven small coral islands and the extraordinary 19th-century Fort Jefferson — a masonry military fortress the size of several city blocks, never completed, never fired in anger, used briefly as a federal prison (it held one of the Lincoln assassination conspirators). The surrounding waters hold the highest coral coverage in the Florida Keys region; snorkeling directly off the ferry dock is exceptional. The park’s primitive campground allows overnight guests who stay after the last ferry leaves — the experience of having the fort to yourself at dusk, with frigatebirds overhead and the mainland an invisible distance away, is one of Florida’s most singular adventures.

The Keys hold a hallowed place in American fishing culture. The flats around Islamorada are the historical center of backcountry fly fishing for bonefish, permit, and tarpon — the so-called Holy Trinity of saltwater fly fishing. Zane Grey, Ted Williams, and generations of serious anglers have come for the spring tarpon run (April–June) when fish to 200 pounds roll through the channels. The guides who work these flats represent some of the most skilled watermen in America.