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Aguadilla

Occupying a small sliver of land wedged between Hwy 2 and the sea, Aguadilla is a small coastal city of surprising contradictions. Its world-class surf scene draws visitors from all over. Nearby, there's a graying campus of a retired US Air Force base known as the Ramey Base.

Brightly painted wooden fishing boats pulled onto a Puerto Rico beach beside a palm-covered headland and calm blue sea

Getty Images/AWL Images RM

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