With almost 500 years of history behind it, San Juan, Puerto Rico is one of the oldest cities flying the U.S. Flag.
Puerto Rico (the island) was discovered by Christopher Columbus in 1493 and the port city of San Juan eventually became an important intermediary stop were almost all European ships would restock before making their long trans-Atlantic crossing back to Europe.
In fact, on their way back to Spain, Spanish Galleons would pass through San Juan loaded with gold and booty from Mexico and South America.
Without question, Old San Juan is one of the gems of the Caribbean with its colorful style and fascinating history.