Capital of Puerto Rico. Population: 437,745; largest city in Puerto Rico and also it's main port. Since Puerto Rico is an island, the port is important.
Originally settled by Ponce de León, he had named it Caparra. Later, during the 16th century, they moved the settlement to the other side of the bay and renamed the town San Juan. Its narrow streets and overhanging balconies often remind visitors of Colonial Times (although any of today's visitors would have no way of knowing what the colonial times looked like :-).