Historical Old San Juan

April 30, 2014 No Comments
El Morro castle at old San Juan

It’s hard to comprehend much of the culture and architecture of San Juan without understanding its history. In 1493, Christopher Columbus happened upon the island of Puerto Rico during his second voyage to the New World. At the time, the island was home to nearly twenty villages of some fifty thousand Taíno Indians, who were kind enough to show the explorer some gold nuggets they found in the river. Columbus immediately claimed the island for Spain and dubbed it San Juan Bautista for St. John the Baptist.

Two decades later, Juan Ponce de León arrived on the island and founded the New World’s second settlement (the first was Santo Domingo in what is now the Dominican Republic). This event took place more than a hundred years before the Pilgrims arrived in Jamestown, Virginia. Ponce de León was named governor of the settlement, which he appropriately called Puerto Rico, literally “rich port”. Later, a Spanish cartographer mistakenly flipped the names on a map, resulting in the city of San Juan on the island of Puerto Rico.

For the next three centuries, imperialism ruled European agendas. Puerto Rico was Spain’s “Key to all the Indies” because of its strategic location for the empire’s control over its New World colonies. By the second half of the eighteenth century, San Juan was one of the most heavily fortified cities in the Americas, and military facilities had taken over the majority of the region.

San Juan became known as La Ciudad Amurallada (The Walled City) in recognition of the forty-foot-high wall that surrounded it. The elaborate fortifications system helped solidify Spanish reign over the island for nearly four hundred years. The fort successfully fended off the British, the French, and the Dutch. In 1898, at the end of the Spanish-American War, Spain ceded Puerto Rico to the United States; the island has since been a US territory.

Today, the part of the city that lies within what remains of the wall is referred to as Old San Juan, which is listed both as a US National Historic Site and a UNESCO World Heritage Site. The area encompasses more than four hundred carefully restored buildings that date back to as early as the sixteenth century, making Old San Juan one of the most well-preserved and history-rich cities in the entire Caribbean region.

The cobblestoned streets are a unique shade of blue. Unlike typical cobblestones, which are made of stone clay, the streets of Old San Juan were laid out with bricks cast out of the remains of the iron-refining process. These cobblestones were initially used as counterweight aboard ships. Upon arrival, the bricks were laid onto the streets to facilitate travel. The moisture of the iron gives them their deep-blue tone and durability. Legend has it that if you listen closely, you can hear the footsteps of the Spanish soldiers who once trod the streets.


Keep your eyes peeled for exotic flora and fauna as you ride your personal ATV along a guided trail through farmlands into the Carabali Rainforest.

Fall in love with the beauty of Puerto Rico’s capital as you tour historical landmarks in Old and New San Juan. Then, enjoy some free time to shop for jewelry and memorable souvenirs.

Discover Puerto Rico’s unique mix of cultures that includes Taino Indians, Spanish explorers, and African slaves, each with their own music, food, dances, and traditions.


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