Founded by the Spanish, this historic gem is the oldest city in the United States and its territories. It remains a living testament to the allure and magic of a bygone era.
For over five centuries, Old San Juan has enchanted visitors with its grand fortresses, towering stone walls, picturesque squares, hidden courtyards, and iconic cobblestone streets — all offering a glimpse into history. Today, however, the city is as lively, vibrant, and colorful as ever. Explore the rich heritage and ageless charm of Old San Juan, one landmark at a time.
A Walled City is Born
Did you know that the names of San Juan and Puerto Rico were once swapped? When Christopher Columbus arrived in 1493, he named the entire island “San Juan Bautista,” while the small islet where the capital now sits was called “Puerto Rico,” meaning “Rich Port.” Long before European explorers arrived, however, the indigenous Taíno people referred to their homeland as Borikén.
In 1508, Juan Ponce de León landed on the island and would later become Puerto Rico’s first Spanish governor. While he’s most famously remembered for his quest to find the Fountain of Youth, his role in shaping the island’s early colonial history is equally important. In 1514, he established Villa Caparra in what is now Guaynabo, marking the first capital of Puerto Rico, located about seven miles inland from the harbor.
Historical records from that time show concerns about Caparra’s location, particularly regarding the difficulty of traveling to and from the islet, poor air circulation, and unhealthy living conditions. Despite these challenges, Ponce de León hesitated to relocate, citing the area’s agricultural potential as a reason to remain.
Building a New Capital
As time passed, the residents of Caparra grew increasingly frustrated with the settlement’s inland location, particularly due to its distance from the main dock where Spanish ships arrived. Seeking a change, they petitioned to move the capital closer to the coast. In 1521, the Spanish Crown approved the relocation, and although the ruins of the original settlement remain, this move marked a pivotal moment in Puerto Rico’s history.
Shifting an entire town was no small task. The Spanish had to first build a road connecting Caparra to the coastal islet, then carefully choose the best spot for essential buildings like the church and town hall. The site they selected is now marked by the Puerta de San Juan — a historic gate that once served as the main entrance to the newly established city. Situated near the pier and a freshwater well, the gate was strategically placed for both functional and ceremonial purposes.
The Puerta de San Juan is the only remaining city gate from the colonial era. It welcomed kings, dignitaries, and travelers into what would become “la ciudad amurallada” — the walled city. Just beyond the gate is El Paseo de la Princesa, a picturesque pedestrian promenade located outside the city walls. Today, it’s a bustling hub, especially on weekends when local artisans and street vendors line the path, greeting visitors as they explore the San Juan National Historic Site.
San Juan’s Historic Gems
1. Castillo San Cristóbal
Constructed between 1634 and 1765, Castillo San Cristóbal has stood for centuries as a formidable sentinel at the eastern entrance of Old San Juan. This impressive fortress was designed to protect the city from land-based attacks, complementing the nearby Castillo San Felipe del Morro. Covering more than 27 acres, it remains the largest fortification built by the Spanish in the Americas. Also known as Fort San Cristóbal, it played a crucial role in defending San Juan Bay against foreign invasions, including during the Battle of San Juan in 1797, when Ralph Abercromby led an assault. The expansive esplanade offers visitors a chance to wander and enjoy stunning views of Old San Juan. This entire defense system, now part of the San Juan National Historic Site, has been recognized as a UNESCO World Heritage Site since 1983.
2. Catedral de San Juan Bautista
Old San Juan’s revered cathedral stands as the most significant religious structure in Puerto Rico and one of the most historically important. Known as the Cathedral of San Juan Bautista, it serves as the seat of the Archdiocese of Puerto Rico. It is also recognized as the oldest church on U.S. territory and the second oldest in the Western Hemisphere. The cathedral’s origins trace back to 1521, during the early days of Spanish colonization. However, the original structure was destroyed by a hurricane, and the current building dates to 1540.
The cathedral’s striking Gothic-style façade didn’t appear overnight—it evolved gradually over the centuries, shaped by time and events.
Throughout its long history, the cathedral has faced many challenges. It has endured multiple attacks and acts of looting, the most infamous of which occurred in 1598, when English forces led by the Earl of Cumberland—who launched the only successful assault on El Morro—ransacked the city and plundered the church. Natural disasters also took their toll; in 1615, a second powerful hurricane ripped the roof off the building, adding to its legacy of resilience and restoration.
3. Museo Casa Blanca
Originally constructed in 1521 as the official residence of Puerto Rico’s first governor, Juan Ponce de León, this historic site holds the distinction of being the oldest home in Old San Juan. Today, the building functions as a museum, showcasing artifacts from the 16th and 17th centuries that offer a glimpse into the island’s colonial past.
Museum Hours:
Wednesday to Sunday
8:00 AM – 11:45 AM
1:00 PM – 4:00 PM
4. San José Church
Founded in 1532 during the era of Spanish rule, this church is the second oldest in the Americas and a striking example of Gothic architecture from that period. For 350 years, it served as the resting place of Juan Ponce de León, whose coat of arms remains visible within the church. It is also the final burial site of José Campeche, one of Puerto Rico’s most celebrated artists. Ongoing preservation efforts began in 2003 after the church was recognized as one of the most endangered historic sites in the United States due to its significant structural decline.
5. Hotel El Convento
Nestled in the heart of Old San Juan, this boutique hotel blends old-world charm with modern luxury as a proud member of the Small Luxury Hotels of the World. Just steps away from renowned museums, historic sites, and the city’s vibrant nightlife, the hotel offers an ideal location for exploring the cultural richness of Puerto Rico.
Guests enjoy access to the El Convento Beach Club, which provides beach and pool privileges at sister properties located along some of the island’s most beautiful beaches. Complimentary high-speed internet is available throughout all guest rooms and public spaces, and each evening, guests are invited to a complimentary wine and cheese reception at La Veranda Terrace, featuring a curated selection of wines and hors d’oeuvres.
Hotel El Convento is a distinguished 4-star, five-story property in the heart of Old San Juan, making it a highlight of Puerto Rico tourism. Centered around a stunning interior courtyard, the hotel features a rooftop pool on the fourth-floor terrace, a well-equipped fitness center, and a quiet library — all offering breathtaking views of the historic cityscape.
A must-visit for culinary enthusiasts exploring Puerto Rico tourism, the hotel’s signature restaurant, El Patio del Níspero, serves gourmet breakfast, lunch, and dinner in an elegant outdoor setting beneath a centuries-old nispero tree. With its blend of colonial charm and modern luxury, Hotel El Convento offers an unforgettable experience for travelers seeking the best of Puerto Rico.
