For travelers looking to trade winter layers for Caribbean sunshine without giving up culture, San Juan offers a particularly layered escape. On a secluded beachfront peninsula just minutes from Old San Juan, Caribe Hilton puts beach time, Puerto Rican history and the city’s distinctive culinary and cultural character within easy reach.

The resort itself is part of that story. At Caribar, guests can order the original piña colada, created at the property in 1954, before heading into Old San Juan to explore its colorful streets and historic architecture. Back at the resort, Puerto Rican specialties such as mofongo and arroz mamposteado sit alongside Italian fare at Rustica, while a new history museum traces Caribe Hilton’s role in Puerto Rico’s tourism, culinary and entertainment history through vintage menus, photographs and memorabilia. Winter also coincides with one of the island’s most distinctive traditions, as Puerto Rico’s holiday celebrations continue well into January.

The Curated Take: San Juan works particularly well for travelers who want warmth without surrendering a sense of place. The beach is only one part of the experience here. History, food, cocktails and the continuing holiday season give a winter escape to Puerto Rico considerably more texture than a conventional resort getaway.