A Historic Walking Tour of Old San Juan, Puerto Rico

If there’s a list out there of the best city walks in the world, Old San Juan must be on it. Blue cobblestone streets, over 400 Spanish colonial buildings from the 16th and 17th centuries painted in pinks, yellows, and blues, and iconic structures that have stood the test of time. . . as well as hurricanes. No wonder Old San Juan is on the U.S. National Register of Historic Places!

The Facts Plain and Simple

Old San Juan refers to the original settlement in Puerto Rico. Walls were built in 1630 around the city to protect it from pirates and European invaders. Today, Old San Juan encompasses a seven-block area of residential and commercial activity.

Christopher Columbus came to San Juan, Puerto Rico in 1493. He claimed the island for Spain and named it San Juan Bautista (John the Baptist). Juan Ponce de Leon founded the first Spanish settlement in 1508. He was later elected governor, and eventually laid to rest there.

Puerto Rico remained under Spanish rule until 1898 when it fell to the United States during the Spanish-American war. Spain ceded the island to the U.S. under the Treaty of Paris.

Roughly 4 million people visit Puerto Rico each year. Some visitors vacation on the island, while others come for the day on one of the numerous cruise ships that dock in San Juan harbor each day. However you get there, it’s an amazing step back in time.

Ready to Walk?

You’ll want a hat, sunblock, water, and good walking shoes for your adventure. Your first stop should be at La Casita Tourism Center, located right across the street from the cruise ship piers. There, you can get a map of Old San Juan, and guides can point you in the right direction. Plan on a full day to walk the streets and take in the sites.

Paseo de la Princesa – Start your walk at Paseo de la Princesa – the historic promenade at the foot of the Old San Juan city walls, measuring 40 feet high, and 12 to 20 feet thick. To your left, is San Juan Bay. On weekends, vendors and musicians line Paseo la Princesa with knick knacks, yummy eats, and a festive atmosphere.

Blue Cobblestone Streets – The original stones were used as ballasts in the European ships that came to Puerto Rico. By 1784, they were being used to pave the streets. Centuries of wear and tear have damaged the stones so they’re being replaced, but in some areas the original stones are still there to admire.


Raices Fountain
– Before you head through the city gate, you’ll want a picture in front of the famed fountain. Bronze, naked goddesses riding horses and dolphins celebrate the diverse ethnic cultures of Puerto Rico.

San Juan City Gate – At this point, you’re walking through one of the oldest gates in the world. At one time there were six gates allowing passage into the city. Today this is the only operational one. It was built in 1635.

Cats, Cats Everywhere! – Legend has it that Christopher Columbus kept cats aboard his ship to keep rats at bay – and some of those cats were left behind in San Juan. Whether true or not, you’ll see plenty of cats roaming the streets, and even in and out of the open doors of Catedral de San Juan Bautista.

Catedral de San Juan Bautista – Construction was begun in 1540. The cathedral was strategically built so travelers could dock their boats, come through the San Juan Gate, and then give thanks to God for a safe journey. The church has withstood hurricanes, robberies, and pillage. Take note of the incredible stained glass windows, statues, and domes. You’ll also find Ponce de Leon’s tomb inside the cathedral. Light a candle, take a seat in a pew, and offer a prayer of your own.

San Juan Cemetery – The cemetery is one of the most beautiful in the world! It’s situated between the city wall, El Morro fort, and the edge of the Atlantic Ocean. Built in 1863, it’s the final home to many prominent Puerto Rican families.

Castillo San Felipe del Morro
– The castle is a spectacular site as you walk up to El Morro. The fort sits above the edge of the Atlantic. Lush green fields encircle it. Today, you’ll find visitors making the trek (roughly 2 million each year) and local families enjoying a picnic, along with some kite flying.

Construction began in 1539 and the Spaniards continued building it until 1786 as they found newer military technology. El Morro has six levels comprised of turrets, towers, dungeons, tunnels, and cannon batteries. The fort rises 140 feet above sea level. It was designed to protect San Juan harbor from attack.

The outer walls are between 6 and 18 feet in depth. El Morro was never defeated by sea and it’s a true marvel of engineering that has survived multiple attacks, and countless storms and hurricanes.

After Puerto Rico was ceded to the United States, El Morro was under U.S. military rule from 1898-1961. During that time it was called “Fort Brooke”. The lands around the fort were used as a hospital, officers’ club, living quarters, a golf course, and a baseball field.

In 1961, El Morro was declared a National Historic Site and is now under the watch of the U.S. Parks Service. During your visit, be sure to have your picture taking in one of the sentry boxes that jut out over the sea.

A Step Back in Time

However long you get to spend in San Juan, enjoy the blue cobblestone streets and the majestic beauty of a time long ago. Appreciate the architecture that has withstood hundreds of years through storms and battles. And be sure to pet the cats!

Are you planning on a trip to Old San Juan? What’s on your list of things to do?

Tags : travel   San Juan   Puerto Rico   

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