1. Islamorada, FL
Lots of people assume Miami and the Florida Keys need to be dealt with as separate vacations, but that’s simply not so. From Miami, it’s an utterly pleasant drive down the Overseas Highway. That name makes sense once you’re on it—stretched over sparkling blue water, the 113-mile throughway connects the narrow, broken-up strip of the Keys back to the mainland.
Islamorada, a small, idyllic beach community traditionally known as a sportfishing capital, is the perfect gateway to exploring what is arguably Florida’s most iconic coastal terrain. The drive from Miami takes less than two hours—though with such brilliant scenery, you’ll want to leave extra time for stopping and taking pictures along the way.
EAT: All-day dining spot Green Turtle Inn, which originally opened in 1947, is alone worth the trip down to sunny Islamorada: standouts like Barney’s Fish Sandwich and the Ultimate Patty Melt earned it a spot on the popular TV show Diners, Drive-Ins & Dives.
DRINK:
Take a break from lazing on the beach and pull up a barstool at Florida Keys Brewing Co., a colorful taproom that occasionally hosts fun events like group painting nights.
DO: The third Thursday of the month is possibly the best time to visit Islamorada, as that’s when Art Walk—a monthly showcase of local artists, sculptors, jewelry makers and musicians—takes over this quarter-mile stretch of the Old Highway.
STAY: If you’re looking to treat yourself to an overnight stay inside a handsomely furnished suite with a generous balcony and deep soaking tub (not to mention three on-site restaurants and two open-air tiki bars), Cheeca Lodge & Spa is the place.
If you do just one thing... Even in you’re just passing through on your way to more southern Keys, there’s perhaps no more iconic detour than stop at Robbie's of Islamorada to feed the massive tarpon off the dock.