4. San Juan, Puerto Rico
“I think San Juan is seriously underrated as an easy long-weekend getaway for visitors from the east coast of the US. Old San Juan oozes charm, and if you stay within the old city’s two-square-mile radius, you won’t need a car for great restaurants, sightseeing and shopping (and, of course, no one needs a passport for Puerto Rico). Hotel Casa Blanca and Villa Herencia are my two fave boutiques there—stylish and affordable.” —Sarah Greaves-Gabbadon, Caribbean travel expert
More info on San Juan here.