Taking a stroll along Old San Juan’s iconic blue cobblestone streets back to the 16th century.

Strike it Rich in Old San Juan

By Anita Draycott

Take a stroll along Old San Juan’s iconic blue cobblestone streets (used as ballast on Spanish galleons) back to the 16th century.

The oldest colony is North America, first discovered by Christopher Columbus in 1493 and declared a World UNESCO Site in 1983, is a seven-block wonder, dominated by the six-level fortress El Morro, rising 150 feet above the turquoise Atlantic surf.

Columbus originally called the island San Juan Bautista after St. John the Baptist. However, thanks to favourable trade winds and the ambitious efforts of the first governor, Juan Ponce de Leon, the island became Spain’s most important Caribbean outport through which trading ships passed laden with gold, silver, spices and all manner of treasures—hence its later name, Puerto Rico (Spanish for rich port). Eventually, San Juan became the name for Puerto Rico’s capital and main port.

Enter through the San Juan gate and you’ll discover a vibrant mix of Old World landmarks, flower-festooned wrought iron balconies, trendy boutiques, atmospheric restaurants and clubs where you can swivel your hips ‘til the wee hours. Remember, San Juan is the birthplace of pop star Ricky Martin.

In 1947, Puerto Rico became a Commonwealth of the U.S., but inside the old walls the vibe is more Spanish/ Caribbean than American. The ethnic mix of Taino (Amerindians), African (slaves) and Spanish is reflected in the island’s cuisine, festivals and music. Put two Puerto Ricans together with a bottle of local Don Q rum and you’re guaranteed a party.

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