Driving down the Overseas Highway from Miami to Key West feels like slowly decompressing from the world at large. (The Seven Mile Bridge will make you feel like you’re soaring over the water.) The necklace of islands strung together by this 127.5-mile road vary markedly, moving from the Upper Keys, which seem like shards of the mainland cast off into the ocean, on to the Middle and Lower Keys. The final stop is Key West, a.k.a the Conch Republic. The journey only takes four hours total (though watch for delays, as traffic accidents can block the road and make passing impossible). If you can, earmark a week to meander down and explore hidden corners at your own pace.
Where to stop: Press on through the Upper Keys, which can feel a little gimmicky thanks to an abundance of souvenir shops, and instead linger in the Middle and Lower Keys en route to Key West. Go spearfishing near Marathon with one of the local fishing charters or sunbathe in the wilderness of Bahia Honda State Park, one of the prettiest spots in the Keys. Sandy beaches are rare elsewhere on the archipelago, but you’ll find several here.
Where to eat: You’re going to want to try Key Lime Pie in its spiritual home—debates rage as to the best, but we’d start with a slice at Blue Heaven, an al fresco restaurant with a yard full of chickens—but don’t miss the chance to detour for a pizza and a pint at the No Name Pub, too. Located on a hard-to-find island where Cuban patriots staged rehearsals for the Bay of Pigs invasion, the pub’s interior is covered with currency stapled to almost every surface. Ask to borrow the staple gun if you want to add to your own.
Where to stay: Key West is surprisingly large, and much of the accommodation is clustered around the eastern edges—avoid this at all costs, as it’s a long hike from the main drag on Duval. Instead, splurge for one of the 19th-century cottages at Winslow’s Bungalows downtown.