Built by the Spanish, this historic treasure is the oldest city in the United States and its territories — and it continues to exude the timeless charm and enchantment of the past.
For over 500 years, the historic walled city of Old San Juan has captivated visitors with its massive fortresses, soaring stone walls, charming plazas, tucked-away courtyards, and iconic cobblestone streets — all evoking the feeling of stepping into another era. Yet today, the city feels more vibrant, colorful, and full of life than ever before. Discover Old San Juan’s rich past and timeless beauty, one landmark at a time.
A Walled City is Born
Did you know that the names of San Juan and Puerto Rico were originally reversed? When Christopher Columbus arrived in 1493, he named the entire Island San Juan Bautista, while the small islet where the capital now stands was called Puerto Rico — meaning “Rich Port.” Long before European arrival, however, the native Taínos called their homeland Borikén.
In 1508, Juan Ponce de León arrived and later became Puerto Rico’s first Spanish governor. Although he is famously linked to the legendary search for the fountain of youth, his impact on the Island’s early colonial history is significant. In 1514, he founded Villa Caparra in what is now Guaynabo, making it the first capital of Puerto Rico, located roughly seven miles inland from the port.
Historical records reveal concerns at the time about Caparra’s location — particularly the challenges of travel to and from the islet, poor air circulation, and unhealthy living conditions. Despite this, Ponce de León was reluctant to move, citing the area’s agricultural value as a reason to stay.
Building a New Capital
Over time, the residents of Caparra grew frustrated with the inland location, especially since it was far from the main dock where Spanish ships arrived. Pressing for change, they petitioned to move the capital closer to the coast. In 1521, the Spanish Crown approved the relocation — and while the original settlement’s ruins still exist today, the transformation marked a turning point in Puerto Rico’s history.
Relocating an entire town was no simple feat. The Spaniards first had to construct a road from Caparra to the islet and carefully select the ideal site for key structures like the church and town hall. That chosen spot is now marked by the Puerta de San Juan — a historic gateway that once served as the main entrance to the new city. Flanked by the pier and a freshwater well, this gate was strategically located for both practical and ceremonial purposes.
The Puerta de San Juan, the only surviving city gate from the colonial period, welcomed kings, dignitaries, and travelers into what would become la ciudad amurallada, or “the walled city.” Just beyond the gate lies El Paseo de la Princesa, a scenic pedestrian promenade outside the city walls. Today, it’s a lively gathering place, especially on weekends, when artisans and street vendors line the path to greet visitors exploring the San Juan National Historic Site.
San Juan’s Historic Gems
1. Castillo San Cristóbal
Built from 1634 until 1765, for centuries the Castillo San Cristóbal has been standing guard at the eastern gate of Old San Juan. The imposing fortress was built to guard the city from enemies approaching by land, serving as a counterpart to Castillo San Felipe del Morro. The citadel covers over 27 acres and is the largest one made by the Spaniards in the New World. Fort San Cristóbal, as it is also known, defended the San Juan Bay from foreign attacks, such as the Battle of San Juan in 1797, perpetrated by Ralph Abercromby. The vast esplanade is a great place to explore around and enjoy the beautiful view of Old San Juan. This whole system, which is San Juan National Historic Site of defense, has been a UNESCO World Heritage Site since 1983.
2. Catedral de San Juan Bautista
Old San Juan’s venerated cathedral is Puerto Rico’s grandest religious building, and one of its most important. In fact, San Juan Bautista is the seat of the Archdiocese of Puerto Rico. It’s also the second oldest church in the Western Hemisphere, and the oldest church on U.S. soil. The history of the church dates to 1521 and the earliest beginnings of the Spanish colonization of the island. The building you see today wasn’t the original church, which was demolished by a hurricane. The current structure dates to 1540.
Even then, the elegant gothic facade that you see today evolved over centuries.
The cathedral has also been through its share of trials and tribulations. Over time it’s succumbed to numerous robberies and pillaging, most notably in 1598, when troops under the Earl of Cumberland (who famously launched the only successful attack on El Morro) sacked the city and looted the church. It’s also had its share of weather-related wear and tear, especially in 1615, when a second hurricane came along and took off its roof.
3. Museo Casa Blanca
Originally built in 1521 as the main residence for Puerto Rico’s first governor, Juan Ponce de León, this landmark is Old San Juan’s oldest residence. Nowadays, the residence serves as a museum housing 16th and 17th-century artifacts.
Museums Hours of Operation:
Wednesday to Sunday
8:00AM – 11:45AM
1:00PM – 4:00PM
4. San José Church
The second oldest church in the Americas was established in 1532 under Spanish rule, and it highlights the Gothic architecture of the time. It was the resting place of Juan Ponce de León for 350 years, and it still bears his coat of arms. It remains the final resting place of José Campeche, one of Puerto Rico’s most revered artists. Since 2003, the church has been under works for preservation, and it was named one of the US’ most endangered sites due to its deterioration.
5. Hotel El Convento
Located in the heart of Old San Juan, old world charm and elegance meet contemporary comfort in this Small Luxury Hotel of the World. Within walking distance of world-class museums, historic landmarks, and vibrant nightlife. Access to El Convento Beach Club, featuring beach and pool privileges at our sister properties, located on the best beaches in Puerto Rico. The Hotel also has complimentary high-speed Internet access, in all guest rooms and public areas and a daily complimentary wine & cheese, serving a variety of wine and hors d’oeuvres at La Veranda Terrace. Hotel El Convento, a 4-star small luxury hotel with five stories, a central courtyard, a pool on the fourth-floor terrace, gym, library, and great views of Old San Juan. It has one restaurant: El Patio del Níspero which offers a gourmet outdoor breakfast, lunch, and dinner menu.
