14 Coastal Towns That Feel Like a Slice of the Mediterranean

12. San Juan, Puerto Rico – A Historic Coastal Haven

With its pastel-colored colonial buildings, sun-drenched plazas, and lively harborside cafés, San Juan, Puerto Rico, feels like a tropical Valencia or a Caribbean Barcelona. The city’s cobblestone streets, centuries-old Spanish fortresses, and lively open-air markets blend the best of European heritage with a relaxed island atmosphere, creating a coastal town that radiates Old World Mediterranean charm. San Juan’s historic core, Old San Juan, is a masterpiece of Spanish colonial architecture, with its vividly painted buildings, wrought-iron balconies, and winding alleyways that lead to hidden courtyards and secret gardens—reminiscent of cities along Spain’s Mediterranean coastline. The Castillo San Felipe del Morro, a massive 16th-century fortress standing guard over the Atlantic, offers a stunning vantage point that could easily be mistaken for a Moorish castle in southern Spain. Meanwhile, the city’s bustling waterfront, buzzing with fishing boats, lively cantinas, and sun-kissed promenades, mirrors the energy of Naples or Marseille, where the sea is at the heart of life.