1. Old San Juan
San Juan, Puerto Rico
Though Puerto Rico is technically a territory of the United States, there's no debating the fact that Old San Juan is nothing short of a jaw-dropping stunner. With Old World charm, winding streets, colorful Spanish colonial row houses, and a 42ft wall surrounding the waterfront island where Old San Juan is perched, the neighborhood’s breathtaking views assault the eyes with history porn like the 16th-century citadel Morro Castle and the massive La Fortaleza -- built in 1540 on a perch overlooking the sea and today serving as the longest-occupied governor’s mansion in the Western Hemisphere. One visit to this 'hood, and you’ll forget they also have some of the nicest beaches in the Caribbean.
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Jay Gentile is a Thrillist contributor and he always prefers his history lessons with a to-go cup. Follow him: @innerviewmag.