San Juan, Puerto Rico
Travel time: A three- to five-hour nonstop flight from major hubs like JFK, O’Hare, Dallas-Fort Worth, and Miami to the capital city of San Juan will only set you back around $300 to $350 during low season.
Why you'll love it: You don’t need a passport to feel like you’ve stepped out of the country when you amble through San Juan’s tangle of blue cobblestone streets, vibrantly painted alleys, and Spanish colonial buildings draped with bougainvillea. Mighty forts, grand old churches, and remarkable restaurants all host a steady ebb and flow of tourists clambering off cruise ships for a few hours. You, having booked a few nights, get to slow down a bit.
Carve your own trails in Old San Juan to stumble upon offbeat spots like Mi Pequeño, a local shop that makes and sells hand-painted reproductions of San Juan’s doors and building facades. Stop by Caribar at Caribe Hilton, birthplace of the piña colada, and treat yourself to some yummy nosh and cocktails. Explore the brilliant street art of the Santurce neighborhood. Then day-trip: Among the best excursions are Vieques’ bioluminescent bay; the adventure park of Toroverde, where visitors can hop zip-lines -- some of the longest in the world -- over a lush canopy of trees; and El Yunque, the only tropical rainforest in the States. Well, sort of in the States. -- Michelle Rae Uy, Thrillist contributor