Walk Through Puerto Rico’s History in Old San Juan

You don’t have to be a history buff to enjoy the 500-year-old walled city of Old San Juan. Its rainbow-hued Spanish colonial architecture, imposing forts that stretch above the Caribbean Sea and charming cobblestone streets beg exploration. Old San Juan is fairly compact, so you can make the most of a walking tour without rushing. You can even use your phone’s GPS or Google Maps if you need to. Puerto Rico is a U.S. territory, so phone service from most major U.S. carriers works here. Walk through this list from beginning to end, vice versa or just pick and choose a few of your “must see” stops. You’ll soon see why Old San Juan is one of the most visited cities in the Caribbean.

Getting there: If you’re staying in the Condado/Isla Verde area, you can take an Uber and ask to be dropped off at Doña Fela (parking area). If you’re driving, you can park at Doña Fela for less than $2/hr. Pay your ticket at the kiosks on the lobby level before you leave. 

Fort Castillo San Cristóbal is part of the San Juan National Historic Site, which also includes Castillo San Felipe del Morro, San Juan de la Cruz (also called El Canuelo) and most of the city walls. Constructed mainly from 1765 to 1785, the fort was built to protect San Juan against land-based attacks. It’s the largest fortification ever built by the Spanish in the New World. 

The site spans nearly 27 acres and rises about 150 feet above sea level, providing stunning views of both the city and sea. Notable features of Castillo San Cristóbal include rooms for canons, an extensive tunnel system, a bunker, dungeon, moat, plaza and two observation posts that were added during World War II. Currently, you can explore the site yourself, as ranger-led tours are paused due to COVID-19. 

Cost: $10/pp, children under 15 admitted free. Your receipt also gets you into El Castillo San Felipe del Morro (and vice versa).

Hours: Open daily 9:30am–4:30pm (except Thanksgiving, Christmas and New Year’s Day)

Strolling through the streets of Puerto Rico’s capital, it’s easy to find photo-worthy spots. However, this is perhaps one of the most Instagrammable locations in Old San Juan. You might spy a canopy of colorful umbrellas floating between buildings. This post-Hurricane Maria art installation, called the Umbrella Sky Project, was created to inspire hope and reflect the country’s resilient spirit. Sometimes the umbrellas are replaced with kites or the Puerto Rican flag. Fortaleza Street bustles with chaotic energy in the best possible way. Take time to soak it in. It teems with perfumeries, shops, hotels, jewelry stores, restaurants and bars. Also, it’s partially closed to vehicular traffic, so it’s easier to navigate.

Situated near the San Juan Gate at Recinto Street, La Fortaleza captures your eye with its stunning light blue and white facade and tiled roof. Constructed between 1533 and 1540, it was the first fortification built in the San Juan harbor and is the oldest continuously used governor’s mansion in the Western hemisphere (170 governors have lived here). La Fortaleza earned a UNESCO World Heritage Site designation in 1983. It still serves as the official residence and offices of Puerto Rico’s governor today, but 30-minute guided tours are offered weekdays between 8:15am and 3:30pm. The tour includes the verdant Moorish gardens, chapel and dungeon. Special holidays or government business may alter hours of operation, so you might want to call ahead to confirm.

Cost: N/A

Hours: Open Monday through Friday from 9am–5pm

If you need to take a rest from sightseeing, Plaza de Armas (Arms Square) is the place to do it. Let the bubbling waters from the marble fountain soothe you as you people watch in what was once the city’s main town square. Grab a snack or a refreshing iced coffee from one of the nearby food kiosks.

Dating back to 1521, this historic landmark is located in the heart of Old San Juan. The Gothic-style Catedral de San Juan Bautista is one of the oldest buildings in San Juan and is still an operational church. Inside you’ll find beautiful frescoes and stained glass windows. The cathedral also contains the tomb of Spanish explorer and Puerto Rico’s first governor Juan Ponce de León, as well as the glass-encased mummified remains of St. Pio, a Roman martyr killed for his faith.

Cost: There’s no charge to enter, but consider a donation to help with ongoing restoration work. 

Hours: Open Monday through Friday 9am–4pm; Sunday from 8am–1pm; closed Saturday

Museo de las Américas is located on the second floor of the historic Cuartel de Ballajá.

During the 1800s, Cuartel de Ballajá served as military barracks, housing more than 1,000 soldiers at a time. Four permanent exhibitions provide an extensive look into the history of the Caribbean and the Americas. Peruse archaeological artifacts, pre-Columbian to modern day artwork and other items. The museum also hosts exhibits by local artists, as well as creative workshops and community events.

Cost: General admission is $6; Children 12 and under, students and visitors over 65 pay $4.

Hours: Open Wednesday through Friday 9am–12pm and 1–4pm; Saturday and Sunday 11am–4pm; Closed Monday and Tuesday. Holidays may affect hours of operation. 

This towering 16th-century citadel was built after La Fortaleza—construction began in 1539 and was completed in 1790. Enhancements to El Castillo San Felipe del Morro continued over the next four centuries, including expanding the thickness of the walls from 6 feet to 18 feet (25 feet in some sections). El Morro was used for several years as a military installation. It became part of the National Park Service in 1961. El Morro and the walled city of Old San Juan were declared UNESCO World Heritage Sites in 1983. The spectacular views from the top level overlooking the San Juan Bay are worth the price of admission. 

Cost: $10/pp, children under 15 admitted free. Your receipt also gets you into Castillo San Cristóbal (and vice versa).

Hours: Open daily from 9am–6pm

Whether you explore all these Old San Juan gems, pick two or three or add some of your own to your tour, time in Old San Juan is always well spent.

Ready for your walking tour in Old San Juan? We got you. Use this map and follow the route to visit these 7 spots.

You might get hungry after your tour of Old San Juan. Here’s a list of a few of our favorite restaurants in the Metro area with amazing views.