WHEN TO GO: Early June is the time to avoid the two-headed monster of the Florida Keys: tourists and oppressive heat.
WHAT TO EXPECT: The Moorings—once a coconut plantation—has eighteen Cape Cod–style cottages (from one to three bedrooms) that face the breezy Atlantic. Each feels like its own private getaway, thanks to the resort’s lushly landscaped acreage and white-sand beach—one of the few in the Keys—which is open only to guests and has been used as a backdrop for Sports Illustrated swimsuit photos. Islamorada itself is a laid-back Old Florida town, with restaurants and a shopping district pleasingly broken up by ample green space.
TYPICAL DAY: Wake up, take a lounge chair on the beach, and read the paper. Then hop on one of the resort’s bikes and head into town. Stop by the numerous small galleries in the Morada Way arts district. Book a diving or snorkeling trip to Cheeca Rocks, a shallow-water reef a mile offshore, or kayak into the backcountry. Fishermen have a few options: Early June is a great time for tarpon. The resort can hook you up with a guide, or just string up a fly rod and hit the bonefish flat right in front of the property. At day’s end, head to the resort’s Morada Bay Beach Café, grab a rum cocktail, and watch the sun set. Stay for a dinner of conch fritters followed by the day’s catch.
GETTING THERE: Fly into either Miami or Fort Lauderdale, and drive an hour and a half south. Or fly into Key West, then make the beautiful eighty-mile drive north through Big Pine and Marathon keys. themooringsvillage.com