El Viejo San Juan is the core of one of the Americas' oldest still existing cities, and this year Puerto Rico has been marking the 500th anniversary of its founding in 1521 by Juan Ponce de León (of Florida Fountain of Youth fame). Its strategic location made it the first stop of many merchant and military ships traveling from Spain to the rest of the empire's colonies, so it's packed not just with the requisite cobblestone streets, plazas and charming Spanish colonial architecture (now housing a plethora of bars, restaurants, shops, art galleries, and boutique hotels) but also major military, civil, and ecclesiastical landmarks.
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