Walking Tour of old San Juan

Historic San Juan in a day Walking Tour

Whether you have an extended stay in Puerto Rico, or less than a day from a cruise stop over, here’s my walkable itinerary for seeing the best of San Juan.Puerto Rico in one day! Experience history, art, shopping, and admire tons of cool city architecture. 

Start

The San Juan Port in the historic area. Grab some bottles of water from the shops around the port as you’ll head up the hill on Calle Marina street to Castillo San Cristobal, the largest fort built by the Spanish in the New world. 

Distance ~0.5 miles 

Along the way you’ll pass some squares with little shop tents if you’re a fan of the blown glass, one of the tents that is along the way makes little blown glass animals right there for figurines or jewelry. You’ll also see lots of brightly colored buildings and as you finish the uphill trek, you get an awesome view of the port looking down on the big ships docked there.

Peak down all the colorful alleyways as you trek up the short hill

Vising Castillo San Cristobal

Hours: 9:00-6:00 PM everyday 

Cost: (16+): $7.00 

*If you have a National Parks Pass, you can get 4 adults entry for free. 

This fort as mentioned is the largest Spanish fort in the Americas, spanning 27 acres. It took 150 years to build with construction beginning in 1634. It covers the Eastern gate of San Juan Island and its walls extend in either direction of the coast. There are 3 levels to explore: cannon embrasures, sentry boxes, tunnels to explore, and exhibits to learn about the former military quarters. All in all, it’s a great stop and won’t take longer than an hour for self-guided tours. 

**You can also get married here.. *swoon*

After San Cristobal, follow the sea coast along Calle Norzagaray where you can explore old parts of the wall that made up San Cristobal’s defenses with multiple garitas (guard towers) and historical markers. Learn about the La Perla area of San Juan where another fort used to be as you make your way to Castillo San Felipe del Morro. Here walk across the great lawn taking in all the kite flyers and the size of this incredible fort perched on the bay. 

Distance ~ 1 mile

Vising Castillo San Felipe del Morro

Hours: 9:00-6:00 PM everyday 

Cost: (16+): $7.00 

*If you have a National Parks Pass, you can get 4 adults entry for free.

If you have to choose between visiting the 2 forts, this would be the one to go with. While overall containing less “acres” than San Cristobal, this fort has 6 levels and unparallel’d views of the bay and San Juan Isle. While San Cristobal was built to defend against land invasions primarily, this fort was built to defend the bay. And defend it did as there is only one instance where the fort was penetrated by enemy invaders making it the most successful of all the Spanish forts built at that time. Construction began in the 1500s when the battery and tower were built to protect the harbor. In 1632, the governor of San Juan began construction on San Cristobal and the city walls. It was also the center of Spanish life at the time so the structures contained within the fort have a lot more complexity making the tour a bit more interesting.

After a visit to the fort, walk down the stairs on the right/ East side to the start of multiple trails. If you follow the same trail to the right/ East it will take you to the cemetery you pass as you approached the fort from the street. Heading left/ West the path wraps around the bottom of the fort and connects to the Paseo del Moro trail. 

Views looking East along the Paseo del Moro trail 

Paseo del Moro

This trail was my favorite part of San Juan. (shocker right.. I do love trails) It follows the old wall almost around the entire western side of Old San Juan with nothing else along the way besides the ocean and cats. The old wall has been wonderfully maintained dating all the way back to 1630! Between the wall and the ocean, it’s like walking into Pirates of the Caribbean scene.  Along the trail you can also watch the big ships leave from port back to the open ocean easily catch wildlife (other than cats) out in the water.  The area directly under the fort has multiple tide pools that can be peaked into, but be careful not to slip on the wet rocks or get soaked by a sneaky wave. 

Watching a large ship sail out of San Juan Bay

The area which is maintained by the NPS like the forts, is also serving as a cat sanctuary with little cat boxes, food, and water to help the strays out. There were so many adorable cats, most of which won’t let you get too close but will play with a bit of string if you have some. (My dad led a cat by the string quite a ways down the path as it follow and continually pounced on it)

After following the trail a ways (approx. 0.75 miles)  you’ll have two options to make you way back into town and then back to the port. The first option is to turn in at the Puerta De San Juan The Iconic red gate that served as the doorway for dignitaries and bishops to enter into San Juan back when there were only 5 gates into the city.  

Or another 5 minutes down the path, the trail ends at a beautiful fountain on the Paseo de la Princesa which is lined with shops, galleries, and also includes for those of you who skipped out on bathrooms at the forts, a public toilet.

Watching a cruise ship sail past the old San Juan walls out into open ocean 

Both gates are great options and worth seeing if you have to backtrack as the path between the two has beautiful trees overhanging the path and the fountain is really cool. The old gate takes you down Caleta de San Juan straight to the San Juan Bautista Cathedral. From either location, make sure to head over to Fortaleza street to see the fun umbrella covered walkway and explore more little shops and restaurants. And from there with whatever time you have remaining, head back to your hotel or cruise ship. 

Distance ~ 0.75 miles depending on the road you take

Walking Distance for entire loop ~ 3 miles/ 5 km

Colorful buildings of San Juan visible over the old wall

The Paseo del Moro is also a wonderful walk to do at sunset 

Other Points of Interest around San Juan to check out in a day:

Museum of Arts of Puerto Rico

Condado Beach 

El Yungue National Forest and waterfalls 

Tour of the Bacardi Distillery