Miles from Naples: 167
There are few places on Earth with equally stunning sunrises and sunsets. But visitors to Islamorada, a village of small islands in the Florida Keys, can start their days saluting the sun over the Atlantic Ocean and end their evenings watching it set the Florida Bay ablaze. Even more beauty awaits underwater where reefs and shipwrecks provide a playground for sea creatures. On land, this unassuming destination recalls the Keys of yesteryear, with plenty of pristine vistas and island hospitality to go around.
Stay: For relaxed-meets-luxe living, book a villa at The Moorings Village and Spa (themooringsvillage.com). Here, it’s easy to detach from modern life while swaying in one of many hammocks dotting the private beach. Afterward, take to the water by paddleboard or kayak, or bike around the property, stopping to smell the orchids and greet the friendly neighborhood cats. This land was once a coconut plantation, and plentiful palm trees shade the 18 cottages, each nestled in its own pocket of paradise.
Eat: Every Moorings villa has a kitchen, and the resort can coordinate private chef services. But there are many local bites to sample, too. Begin at Pierre’s, The Moorings’ upscale restaurant located across the street in a plantation house decked with Asian-inspired decor. In addition to a stellar sunset view, Pierre’s offers French-fusion food with an island essence, such as the seafood curry with forbidden black rice and bok choy.
Beyond its namesake pie, the Keys are also legendary for conch. Sample it in the form of conch chowder and perfectly fried conch fritters at Lazy Days (lazydaysislamorada.com). Another institution is the Green Turtle Inn (greenturtleinn.com), which still sells its signature turtle chowder circa 1947. For more crustaceous dishes, opt for the lobster grilled cheese or the Keys benedict made with blue crab.
See + Do: Aquatic pursuits abound, namely sport fishing and ample snorkel and diving locations. Be sure to explore the Spanish shipwreck at the San Pedro Underwater Archaeological Preserve State Park (floridastateparks.org/park/san-pedro). Diving aficionados will also love the History of Diving Museum (divingmuseum.org), home to decades of memorabilia, from the first diving helmet to recovered sunken treasure.
Don’t Miss: Adjacent to The Moorings, The Morada Way Arts and Cultural District (moradaway.org) is a beacon for hand-crafted awesomeness, complete with galleries, the Morada Way Clay studio, and the Florida Keys Brewing Co. (floridakeysbrewingco.com). Stop by the monthly Art Walk (held every third Thursday) for music, artisan vendors, and a dose of quintessential Keys quirkinessweirdness.