San Juan: The Walled City

In Old San Juan, a UNESCO World Heritage Site, colorful Spanish-colonial buildings line blue cobblestoned streets, with stunning historic forts standing guard over the harbor.

November 16, 2017 No Comments
San Juan El Morro Landscape

Locals call Puerto Rico la isla del encanto, “the island of enchantment.” The city of San Juan, its capital, is its heart and soul. Established in 1508 on a tiny islet off Puerto Rico’s northern coast, San Juan is the second-oldest settlement in the New World and the oldest city under US jurisdiction. Today, it’s a place of contrasts—one part appealing historical town, the other part sprawling modern metropolis, an intriguing blend of the old and the new. Towering skyscrapers and five-star hotels are surrounded by intimidating forts, cobblestoned streets, and notable churches.

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 20 villages of some 50,000 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 100 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.

San Juan Old City

Colorful facades add a playful vibe to the streets of Old San Juan.


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 18th 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 40-foot-tall wall that surrounded it. The elaborate fortifications system helped solidify Spanish reign over the island for nearly 400 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.

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 400 carefully restored buildings that date back to as early as the 16th 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.

San Juan Walled City Landscape


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.

From the cruise piers in Old San Juan, it’s a quick walk to Paseo de la Princesa, a peaceful tree-lined promenade that overlooks San Juan Bay. Here, street vendors proffer goods to passersby. This is a great place to grab a quick snack; try a piragua, a refreshing snow-cone-like treat.

The Puerto Rico Tourism Board’s headquarters are housed in La Princesa, the city’s former prison building, which intersects the walkway.

Follow El Paseo along the city wall to the San Juan Gate, which marks the official entrance into the old city. Built in the 18th century, this gate is the last remaining of the six heavy wooden doors that used to close at sundown to protect the city from invaders.

The wall is only one part of Old San Juan’s massive military-defense system. The grandiose fortress, Castillo San Felipe del Morro (El Morro), is situated on a rocky peak on the far western coast of Old San Juan, jutting out imposingly over San Juan Bay from the mainland. Although its foundation was laid in 1539, the fortification was not considered complete until 1787. Throughout its storied history, the fort fell only once: to the British Earl of Cumberland, in 1598.

San Juan Cobblestoned Streets

The Walled City is filled with blue-hued cobblestoned streets.


After Cumberland withdrew his forces, the Spanish improved the site, adding a maze of tunnels, dungeons, and barracks. El Morro evolved into a military masterpiece with 60-foot-high, 18-foot-thick walls and carefully planned steps and ramps for moving men and artillery. By the end of the 18th century, the 70-acre, six-level complex rose 150 feet above the Atlantic Ocean and housed over 400 cannons.

At the edge of El Morro is the last and largest building constructed by the Spaniards in the New World. It served as barracks for the Spanish militia and their families in the late 19th century. Facilities included warehouses, kitchens, dining rooms, prison cells, and stables. Now it houses the Museum of the Americas, which features changing exhibitions and an admirable collection of artifacts.

Whereas El Morro was designed to protect San Juan from enemy invasions by sea, its partner in defense, the 27-acre Castillo de San Cristóbal, was designed to protect the city from attacks on land.

San Juan Coastal Forts

San Juan wows with some of the Caribbean’s best-preserved coastal forts.


Construction of San Cristóbal began in 1634 and was finished in 1790. The fort contained five independent units, each connected by a moat and a tunnel. Impressive in design, each unit was fully self-sufficient in the event that any of the others were to fall. The immense fortress is located on the northeastern edge of the city and boasts a half-mile passageway of strategic walls and tunnels that connect it with El Morro.

Although its name translates to “The Fortress,” La Fortaleza is the least fortress-looking of all the sites. Construction began in 1533, but because La Fortaleza did not have any cannons or permanent troops, the building was almost useless for military purposes. Even if it had housed weapons, La Fortaleza was doomed because it had no command over San Juan Bay. A Spanish historian who saw La Fortaleza when it was first constructed stated that “only blind men could have chosen such a site for a fort.” He suggested that instead the fort should have been built on el morro, a headland at the harbor entrance that stood at the top of a steep slope. Within two years, Spain approved funds to build El Morro.

San Juan El Morro Cannon Balls

El Morro has been lauded as a military masterpiece.


From 1640 onward, La Fortaleza was used as the official governor’s residence. In 1846, its facade was redesigned to look as it does today. Over the years, it has been home to approximately 170 governors, and it remains the residence and offices of Puerto Rico’s governor. The large blue structure is currently the oldest governor’s mansion in continuous use in the Western Hemisphere.

Not all of San Juan’s architectural masterpieces are fortresses. The San Juan Cathedral is the second-oldest cathedral in the Western Hemisphere. The magnificent structure seen today is the result of numerous renovations made in 1917. Inside is the marble tomb of San Juan’s first governor, Ponce de León.

One block west of the cathedral is Puerto Rico’s very own White House, the Casa Blanca. Nearby, in San José Plaza, sits the whitewashed San José Church. It’s an excellent example of 16th-century Spanish-Gothic architecture. The church’s construction began in 1523, and Ponce de León himself was buried here for 300 years before his body was moved to the San Juan Cathedral in 1913. If you’re looking to explore beautiful beaches, try the Third Millennium National Park in Old San Juan. The park is home to a historic Spanish fort; the ship-shaped Normandie Hotel; the Sixto Escobar track-and-field stadium; and a food kiosk that offers a special experience with local music, beverages, and snacks.

San Juan Old And New Architecture

San Juan features a combination of old and new architecture.


Taking a short ride east of Old San Juan is like passing through a time warp. Known as the Condado district, “New” San Juan is filled with high-rise hotels, luxury fashion houses, and world-class restaurants, with immediate access to bountiful beaches. It’s also home to the Bacardi Rum Factory. In the late 19th century, the US government created strict standards for its rum factories. As a result, Puerto Rican rums are lauded as some of the finest and smoothest-tasting in the world.

Take a tour of Casa Bacardi, the world’s largest rum distillery, and discover how the No. 1-selling distilled spirit in the US is made. The tour offers opportunities to sample the rum and purchase a bottle or two to take home. More than 70 percent of the rum sold in the United States comes from Puerto Rico, generating $337 million in tax revenue every year.

San Juan El Yunque Path

Narrow paths though the lush grounds of El Yunque lead to cascading waterfalls and a ton of photo ops.


In keeping with its rum tradition, San Juan is known as the birthplace of the piña colada. The frozen cocktail was named the official beverage of Puerto Rico back in 1978. However, the exact origin of the rum-and-coconut concoction is still disputed; both the Beachcomber Bar at the Caribe Hilton Hotel and Restaurant Barrachina claim to be the original creators.

To tour both Old and New San Juan, take an exciting bicycle excursion. The 12-mile-long tour passes both historic sites and pristine beaches. Highlights include El Capitolio (the capitol), home to Puerto Rico’s Legislative Assembly; Escambrón Beach; the San Geronimo ruins; the Santurce Marketplace; and finally, before returning to the pier, the beaches of the Condado district.

Thrill seekers should not miss out on the Original Canopy Tour, located at La Marquesa Forest Reserve. Soar from tree to tree on a network of pulleys and double horizontal cables that are mounted as high as 70 feet over the rainforest floor. The course includes eight traverses, 14 observation platforms, and a series of suspended walkways.

San Juan El Yunque River

Experience the majesty of Mother Nature in the El Yunque Rainforest.


If the natural wonders of Puerto Rico are calling, San Juan is a 45-minute ride from El Yunque Rainforest, the only tropical rainforest in the United States National Forest System. It is relatively small compared with other national forests; however, its 28,000 acres are extremely diverse.

The Luquillo Mountains that rise 3,533 feet above sea level have created a tropical haven for more than 240 species of plants, flowers, and wildlife, including 26 animal species found nowhere else in the world. Visitors can choose to hike through the lush grounds of El Yunque on well-maintained trails or take a horseback ride through the foothills and alongside the clear waters of the Mameyes River.

El Yunque is rooted in legend. One is that it “rains frogs.” When the humidity is particularly high, the tiny coquí tree frogs will climb to the top of the forest canopy. Instead of returning to the forest floor by the same dangerous path lined with predators, the coquí frogs fling themselves into the air. Because they are virtually weightless, they float to the ground unharmed. As such, it appears as if it’s indeed raining frogs.


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Travel into Puerto Rico’s lushly forested mountains to an ecotourism park for an outdoor adventure and zip-line thrills.

Discover Puerto Rico’s rich history, colonial charms, and distinct culture on a narrated tour featuring San Juan’s colonial and modern districts.

Explore the lush, natural beauty of Puerto Rico on horseback at the foothills of El Yunque National Forest.


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