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"Opened in 1949 as the first Hilton outside the U.S. mainland, the Caribe Hilton still projects a glam-trop energy even as it has leaned into family-friendliness; over the years it has attracted celebrities from Gloria Swanson and Elizabeth Taylor to Johnny Depp. With 652 rooms it is one of San Juan’s largest hotels yet the property manages to feel intimate, and it played a notable role in the city's recovery narrative when it reopened after a 15-month closure following Hurricane Maria." - Jessica Chapel