A nature-filled—and surprisingly cosmopolitan—island getaway.
Islamorada, An Upscale Escape
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Nowhere is there clearer proof that the Keys are no longer restricted to the rumrunner-and-conch-fritter crowd than in increasingly tony Islamorada. It’s actually comprised of four islands that, together, are considered the hub of the Upper Keys. Expect sleek restaurants and boutiques, walking trails, and tournament-caliber fishing.

Moorings Village Village & Spa

Even after serving as the backdrop for countless fashion-magazine photo shoots, the Moorings Village & Spa— 18 brightly accented cottages connected to the beach by wooden walkways on a former coconut plantation in the Florida Keys—still seems like your own secret discovery. Lush, almost jungle-like landscaping gives way to a private white-sand beach with swaying hammocks and a thatched-roof dock. Palm trees, hammocks, sand: this is as stripped-down as a vacation experience gets, and one you’d swear couldn’t exist among the shell shops and tiki-festooned marinas of the Florida Keys. At sunset, amble across the road for rum cocktails and conch fritters at Morada Bay Beach Café, or do what the regulars do—bring back some stone-crab claws from the market to devour on your porch with a cold beer.

Robbie's Marina

Lignumvitae Key Botanical State Park

Resting within the central Floriday Keys, Lignumvitae Key Botanical State Park is home to one of the Key's last tropical hardwood hammock forests. William J. Matheson, a wealthy Miami chemist, bought the tiny island and built a caretaker's home (now the visitors center), added electricity through a windmill, and collected rainwater in a cistern. The 280-acre island can only be reached by boat or a guided tour from Robbie's Marina on nearby Islamorada; twice daily, guides showcase the park's 1919 coquina house and outbuildings. Be sure to use bug spray to ward off mosquitoes.

Indian Key

Get a glimpse at the ruins of an early European settlement and some secluded waterfront sands.

Hungry Tarpon

Hole up at a table by the jetty and dine on killer burritos. open for breakfast and lunch only

Squid Row

The tony restaurant, with its private booths, is ideal for a low-lit romantic dinner of Florida lobster.