City Hike of the Top Sites in Old San Juan
Best way to organize your day
Exploring Old San Juan is one of the major highlights of a visit to Puerto Rico. There are a variety of ways to see all the sights, but if you’re hoping for some exercise a self-guided city hike is your best bet.
Have your Uber or taxi driver drop you off at Castillo San Felipe del Morro (El Morro). This impressive fort was built by Spain and took 250 years to complete (1539-1787). It sits high on the cliff overlooking San Juan Bay. You can opt to pay the ten-dollar admission and look at the fascinating exhibits inside or walk along the Paseo del Morro Recreation Trail at the base of the fort. Both ways have breathtaking ocean views.
Travel along El Malécon (boardwalk) and gaze at la Perla, a historic shantytown known for its colorful buildings and seaside location made extra famous by the filming of the “Despacito” video. I suggest viewing it from a distance if you are unfamiliar with the area because it has a reputation for crime.
Continue along to Castillo San Cristobal which guarded Old San Juan from enemy approaches by land and was built from 1634 to 1790. It has impressive views of the coast from Old San Juan to Condado and offers a vantage point of San Juan harbor, La Fortaleza, the Capital Building, and arguably most important, the Bacardi rum distillery, the world’s largest rum factory. Your admission ticket to El Morro covers both forts.
From San Cristobal double back and start meandering through the cobblestone streets of Old San Juan. You can enjoy looking at the multicolored buildings with distinctive Spanish architecture and visiting some of the many churches including Catedrale de San Juan, the oldest cathedral in the United States and Iglesia de San José, one of the earliest surviving examples of 16th-century Spanish Gothic architecture in the Western hemisphere.
At the western end of Sol Street, you are close to El Paseo de la Princesa, the historical promenade and La Puerta de San Juan, the last of the five gates that allowed access into the walled city. La Puerta dates to 1635, is 16 feet tall, and painted a striking shade of red. It acted as the main entrance to San Juan which was heavily guarded and closed at night.
Calle de la Fortaleza has lots of shops and restaurants including Barrachina, one of three establishments that claim to be the birthplace of the pina colada. Most will agree that Fortaleza, the governor’s house, is a more important landmark. Leading up to this mansion is the Umbrella Sky Project art installation. This colorful canopy of umbrellas was hung after Hurricane Maria as a message of hope and inspiration. It can get crowded with tourists clamoring for that perfect Instagram shot so be prepared to wait a bit.
Nearby Plaza de Armas, the city’s historic main square, is the perfect spot to take a break, grab some shade and hang out where the locals often come to sip coffee and mingle.
At the other end of Fortaleza Street is Plaza Colon which is marked by a statue of Christopher Columbus and commemorates the European “discovery” of Puerto Rico. There is a taxi stand, but if you still have some energy, walk along Constitution Avenue for a glance at the Capital building and Paseo de los Presidentes (Walkway of the Presidents). This walkway honors nine presidents who visited Puerto Rico with life-sized bronze statues.
After two to three hours of walking you will have seen most of Old San Juan’s top sights in addition to logging a ton of steps and around 6 or 7 miles. At this point it’s easiest to order an Uber if you’re staying elsewhere in the city. For another active adventure in San Juan check out my post on SUPing in Condado Lagoon and as always make sure to subscribe in the upper right-hand corner so you don’t miss any of my posts.
Helpful Info:
- Bien Papaya: excellent juice and smoothie bar – 500 C. Norzagaray, San Juan
- Restaurante Raices: traditional Puerto Rican food, a bit touristy but good and it gives you a chance to sample dishes such as mofongo – 315 C. Recinto Sur, San Juan
- La Factoria: a vibrant well-known bar for drinks – 148 C. de San Sebastián, San Juan
- Map of Old San Juan
- Chaco’s: tease me all you want but these sandals are great for city hiking in a tropical climate
