Leonida Keys

A tropical island chain stretching south of the mainland, connected by a single scenic highway and hiding everything from resort paradises to smuggler coves.

The Leonida Keys are a shimmering chain of tropical islands dangling off the southern tip of the mainland like a string of emeralds dropped into the Caribbean. Connected by the Overseas Highway — a ribbon of asphalt stretched improbably across miles of open ocean — the Keys feel like another country entirely. Out here, the pace slows to island time, the drinks are always frozen, and nobody asks too many questions about the unmarked boats that pull into the mangrove channels at 3 AM. Each key has its own personality: some are tourist traps packed with souvenir shops and all-inclusive resorts, others are barely inhabited scraps of coral and palm trees where the only residents are pelicans and the occasional fugitive. The diving is world-class, the fishing is legendary, and the sunsets will make you forget that the guy at the next bar stool is almost certainly wanted in at least two states.