Immerse yourself in 500 years of Puerto Rican history and culture on a captivating walking tour of Old San Juan. Discover the beautifully preserved architecture, snap photos, and enjoy water breaks along the way. Join us for a 2.5-hour journey through the walled city!
Immerse yourself in 500 years of Puerto Rican history and culture on a captivating walking tour of Old San Juan. Discover the beautifully preserved architecture, snap photos, and enjoy water breaks along the way. Join us for a 2.5-hour journey through the walled city!
- Plaza Colon - Dedicated to the Genoese explorer, Plaza Colon features a prominent structure showcasing reliefs of Columbus’s first and second voyages, along with a statue of Columbus himself. It serves as the meeting point for the tour.
- Castillo de San Cristobal - Constructed to protect the Islet from land attacks, Castillo San Cristobal now…
- Plaza Colon - Dedicated to the Genoese explorer, Plaza Colon features a prominent structure showcasing reliefs of Columbus’s first and second voyages, along with a statue of Columbus himself. It serves as the meeting point for the tour.
- Castillo de San Cristobal - Constructed to protect the Islet from land attacks, Castillo San Cristobal now covers about half of its original size, making it one of the largest fortifications built by the Spanish Crown in the Americas. (The tour does not enter the castle)
- Plaza de la Barandilla - Unique for not being named after a historical or religious figure, this plaza in Old San Juan connects Calle San Francisco with Calle Luna, featuring the distinctive handrail that gives it its name.
- Plaza de Armas - The first plaza in Old San Juan where military drills were held since the island’s initial settlements in the 16th century. It houses the Town Hall and the old Royal Audience of the Spanish Crown.
- Iglesia de San Jose - Built in 1523, it is the second oldest church in the New World still in use. It exemplifies Spanish Gothic architecture beautifully. Adjacent to it stands the statue of Juan Ponce de Leon, the conquistador and first governor of Puerto Rico. (The church is open to the public on specific days and hours)
- Plaza del Quinto Centenario - Constructed in 1992 to celebrate the 500th anniversary of Old San Juan’s founding, this plaza features various symbols and the iconic Totem.
- Cuartel de Ballaja - Originally built in 1864 by the Spanish Crown, these barracks housed over a thousand officers, soldiers, and some of their families. After the United States’ invasion in 1898, the building was used by the US Military as a hospital until the 1950s.
- La Rogativa - Created by Lindsay Dean, a sculptor from New Zealand who resided on the island, this piece commemorates the 450th anniversary of Old San Juan’s founding and the British attack of 1797.
- La Puerta de San Juan - The last remaining gate, La Puerta de San Juan, provided entry for weary sailors from the old port directly to the San Juan Cathedral.
- La Fortaleza - Palacio de Santa Catalina - The first fortification on the islet, La Fortaleza, as its name suggests, protected the initial settlement of Old San Juan from attacks by native Tainos and later foreign powers. (The tour does not enter the palace)
- Catedral Basilica Menor de San Juan Bautista - Built in 1529, the Cathedral of San Juan contains frescoes, stained glass, religious relics, and the final resting place for some of the city’s notable figures. (Open only on specific occasions, days, and times)
- Paseo de la Princesa - A stunning example of a European-style promenade, Paseo de la Princesa was constructed in the 19th century and named after La Princesa de Asturias. It remains well-preserved and actively used today. This is the final stop of the tour.

- Bottled water included
- Bottled water included
- Gratuities
- Gratuities
Immerse yourself in the past and bask in the charm of the ‘fortified city’ that is Old San Juan. Our knowledgeable guides will take you on a 500-year journey through Puerto Rican history and culture, allowing you to experience some of the hemisphere’s most ancient cities through their stunning, time-honored architecture that is rooted in the founding…
Immerse yourself in the past and bask in the charm of the ‘fortified city’ that is Old San Juan. Our knowledgeable guides will take you on a 500-year journey through Puerto Rican history and culture, allowing you to experience some of the hemisphere’s most ancient cities through their stunning, time-honored architecture that is rooted in the founding days of Old San Juan. Designed with photo spots and hydration intervals, this tour spans two and a half hours.
- Total duration is 3 hours including the walking time from attraction to attraction
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.