WHY IT'S HOT Anchoring Key West's tip since 1920, this legendary escape once hosted Ernest Hemingway, Ethel Merman and Rita Hayworth. A recent $43 million facelift restored the Waldorf Astoria resort to its mid-century splendor.
WHAT TO DO Soak up the sun and surf at the picturesque beach—the largest private stretch of sand on the island. Or spend the evening on famously boisterous Duval Street, jam-packed with shops, galleries and restaurants that serve local fare.
WHO'S BEEN THERE Jennifer Lopez, Cher and Chris Rock have recently flocked to this beachside getaway.