Panoramic view of a garita and La Fortaleza in Old San Juan.

Established in 1521, Old San Juan is the oldest city in the United States.

Five Centuries of History in Old San Juan

For 500 years, the cobblestone streets of the so-called walled city have hidden countless stories and mysteries. 

Visiting Old San Juan is a feast for history buffs. Still, even if you’re not, the impressive fortifications, towering walls, open plazas, and hidden patios are just the ticket for you to travel in time. Built by the Spaniards, this historical gem is the oldest city in the United States and its territories. Yet, it still holds the magic and charm of yesteryear – attracting visitors worldwide.

Structure and objects, monuments, and landmarks hold traces of the past frozen in time. Old San Juan has five centuries of history and is ready to be revealed one building or plaza at a time.

Logo for San Juan's 500 anniversary.

Join the celebrations!

Puerto Rico is celebrating the 500th anniversary of the founding of Old San Juan, the oldest city in the United States. Stay tuned for special events running through June 2022!

Learn more

View of the Puerta de San Juan, which was the original entrance to the walled city when it was built in 1517.

View of the Puerta de San Juan, the original entrance to the walled city when it was built in the 16th century.

A walled city is born

Pop quiz time!

Did you know that San Juan and Puerto Rico’s names switched? The islet was first called Puerto Rico, and San Juan Bautista was the name given by the Spanish conquistador Christopher Columbus to the entire Island in 1493. Before his arrival, the native Taínos called their home Borikén.

Years after the rediscovery of Puerto Rico, in 1508, Juan Ponce de León arrived on the Island. You may know him for his continued search for the fountain of youth, but he became the first Spanish governor of the heart and soul of the Caribbean. In 1514, he founded Villa Caparra. Eventually, the inhabitants insisted on moving the town to the islet, complaining that the settlement was too far from the dock where the ships from Spain arrived. The ruins of that settlement remain today around seven miles from the islet.

Historical documents captured the concerns regarding the dangerousness of traveling between the town and the port, the lack of adequate ventilation, and the poor health conditions of the residents of Caparra. However, Ponce de León insisted on staying for reasons related to agriculture.

It was not until 1521 that the Spanish Crown authorized the settlement to move to the islet. But moving a town is no small task! First, the Spaniards had to build a road from Caparra to the islet and identify the right place to establish the church and the town hall. That “ideal place” was where the Puerta de San Juan remains today, a significant landmark given it was literally the main entrance to the new city, with the pier on one side and a well on the other.

That door, the only remaining entrance from the colonial era, was the main gate of kings and dignitaries into what became la ciudad amurallada or “the walled city.” The door leads to El Paseo de la Princesa (the Princess Promenade), a pedestrian pathway just outside the walls. You can find artisans and street vendors gathering there during the weekends to greet people visiting the National Historic Site.

Learn more about San Juan's landmarks

Map of Puerto Rico

Fun Facts for History Buffs

Calle del Cristo is the oldest street in Old San Juan and has the largest number of religious buildings.

El Morro was built in 1539 to defend the city from attacks by sea. It has six floors and is higher than the Castillo San Cristóbal, built to prevent attacks by land. The white and red flag that flies over El Morro is a Spanish military flag known as the "Cruz de Borgoña."

The Casa Blanca Museum is the oldest sample of Spanish architecture in the United States and Puerto Rico. The structure has 14 rooms and original furniture from the 16th and 17th centuries.

The San José Church is one of the oldest in America and was built in 1532. It recently reopened to the public after being closed for about 20 years for restorations. One of the church's chapels has the governors' crypt, where the remains of the governors of the 16th, 17th, and 18th centuries rest. The ceiling of that chapel has frescoes of mermaids, which poses a mystery.

In the 16th century, Hotel El Convento was a religious school that later became Puerto Rico's first convent in the 17th century with Carmelite nuns.

The oldest spiral staircase in Puerto Rico and America built in mortar in the 16th century is at the back of the San Juan Bautista Cathedral. It has 88 steps and leads to the church bell tower. Access is not open to the public.

The architecture of Old San Juan was made "in grids" and allowed cross-ventilation between its buildings and squares. When you walk through the streets, always look for shade!

The material used to build structures in the 16th century, including forts, is called mortar and consists of limestone, sea sand, and brick.

16th-century houses were single-story, had one or two doors, and had inner gardens. The second floors and balconies were built from the 17th century onwards.

Old San Juan's forts and points of interest

View of the Plaza San José and Ponce de León sculpture.

Juan Ponce de León's sculpture in the Plaza San José was built using bronze from cannons. 

Route of San Juan's 500 Years 

A celebration of history!

On the occasion of the celebration of the 500th anniversary of the walled city, a new route is available for visitors and residents of Puerto Rico. Take a historical tour of Old San Juan, where you’ll discover the magic that lies within the walls. Walk the blue cobblestone streets as you explore colonial architecture, find secret pathways, and fall in love with the Island’s history. You’ll get the chance to travel back to the 16th century and visit the most emblematic places of one of the oldest cities in America.

What you should know about the tour:

  • The tour lasts approximately two and a half hours.
  • There will be tours at 9:00 a.m., 10:00 a.m., 1:00 p.m., and 2:00 p.m.
  • Groups will be up to 20 people.
  • There will be an ASL interpreter in the 2:00 p.m. group.
  • Participants must wear comfortable footwear and suitable clothing to access religious facilities.
  • Evidence of vaccination and face mask use will be required.
  • To book your space, reach out to:

​​​​​​​Things to Do in San Juan

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