1 Day in Old San Juan

Old San Juan reminded us of a charming European city with its cobblestone roads and colorful buildings. The vibrantly colored buildings paired with the lively music, food and people we encountered made for a very fun day exploring Old San Juan. With the Castle and Fortress (on the shoreline), Old San Juan is a delight for any history buff as well.  We recommend spending at least a day exploring Old San Juan.  Here is our guide for 1 day in Old San Juan.  For more Puerto Rico tips, see our 1 Week in Puerto Rico Itinerary and El Yunque National Rainforest Guide.

1Day Old San Juan

FYI: This post is based on a trip taken in early March.  We took this trip with our 7 month old daughter.  For more baby travel tips, see Top 10 Baby Travel Tips, How to Hike with a Baby, 5 Top Baby & Toddler Flying Tips and Flying with a Baby posts. 

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1 Day in Old San Juan: Walk Around Old San Juan

If you do nothing else in San Juan, be sure to do at least this. We highly recommend walking around the entirety (a couple miles of walking) of Old San Juan, including the waterfront, to experience the culture and see all it has to offer.  Simply park at one spot (see below where to park for FREE) and make a big loop.  Be sure to also pop down random streets, not always walking on the main roads.  We found some of the cutest spots when we were off the beaten path.  If you love photography like Natalie, you will love finding these quaint and colorful spots.  We also found some fun murals tucked away on less trafficked streets. 

1 Day in Old San Juan

Castillo San Cristobal and El Morro Fortress 

Beyond the cobblestone streets and colorful buildings, be sure to visit El Morro Fortress and Castillo San Cristobal on the coastline with 1 day in Old San Juan.  El Moro was constructed in the 1400s to protect San Juan from pirates. The architecture here is really spectacular and provides for some awesome photo ops. Castillo San Cristobal is located just south of the fortress on the shoreline and has similar cool old architecture.  

1 Day in Old San Juan

Tip: America the Beautiful pass will get you into both Castillo San Cristobal & El Morro Fortress for free.

Otherwise, entrance to each is $10/person (as of March 2022 when we visited). If you have 2 or more people in your family and plan to visit any other National Park Service site in the year, buying the America the Beautiful pass is completely worth it as it pays for itself and gives you access to all the other National Park Service sites for free.  We buy this pass every year if we plan to visit 2 or more National Park Sites.  

Also, you do not have to buy the America the Beautiful Pass at the beginning of the year as it is valid for a year from the month of purchase. The pass is actually good for 13 months if you time it right.  For example, we bought our last pass in the very beginning of October 2021 and it will be good through the end of October 2022. 

IMPORTANT: You have to get the physical pass to use it so be sure to see how long it will take to ship (typically about 2 weeks unless expedited) to make sure you get this pass in time for your trip. 

La Fortaleza/Calle Fortaleza

Another spot you want to make sure you visit with 1 day in Old San Juan is La Fortaleza/Calle Fortaleza, the Governor’s Mansion and the street in front of it.  Typically Calle Fortaleza is very picturesque and has umbrellas hanging above the street but when we visited, this was not the case.  A local told us the objects hanging above the street rotate throughout the year so do not expect to necessarily see this decor. 

Tip: Park near El Morro for FREE

Across the street a couple blocks east, we were able to park on a Sunday morning for free.  Here is the location we parked at for free.  Be sure to read all signs, as this could change at any time.  Signs are in Spanish so either ask a local or use Google translate if you do not speak Spanish to be sure it is OK to park there

Old San Juan

Tip: Arrive early as it gets busier throughout the day 

We were able to drive into Old San Juan quickly without any traffic but when we were leaving in the afternoon, the traffic to get into Old San Juan was bumper to bumper.  The National Park Sites were also quite crowded at that time.  We like people, not crowds!  

Parent advice: You can navigate Old San Juan with a stroller but ideally would babywear  

It is a bit tricky but doable to use your stroller in Old San Juan. In Old San Juan, the roads are mainly cobblestone but you can roll your stroller on the sidewalks.  The sidewalks are not always continuous and sometimes we had to lift our stroller up or carry it briefly.  However, it worked and was worth the extra effort for us.  We prefer to have our stroller, when we can, as it serves as a portable napping spot for our baby. Having our stroller allows the baby to sleep quite well almost anywhere. A well rested baby is a happy baby!  For more on this and all our baby travel tips see our Top 10 Baby Travel Tips, How to Hike with a Baby and Flying with a Baby posts.

Check Out Barrichina, Home to the Original Pina Colada

Be sure to get some traditional Puerto Rican food or check out one of the many other types of restaurants in Old San Juan.  We recommend eating at Barrachina (specializes in traditional Caribbean food).  It has a beautiful enclosed outdoor dining area and is, allegeddy, home to the “Original” Pina Colada.  There is debate between two restaurants (Barrichina and Caribe Hilton Hotel) as to which establishment the Pina Colada was first created in the 20th century.  Regardless if it is the home to the Original Pina Colada or not, the Pina Colada at Barrachina sure was delicious. Maybe try Pina Coladas at both spots and determine which one you think is the original?!  If you have time for another meal, consider checking out Jose Enrique’s Restaurant, a casual establishment known for great Puerto Rican food, while in Old San Juan. 

1 Day in Old San Juan: Walking Map of Old San Juan

1 Day in Old San Juan Walking Map

Where to Stay when Visiting Old San Juan

Stay East of Old San Juan

We recommend staying at the The East Point P.R. Airbnb we stayed at in Ceiba (East of the Island) just south of Fjarado and about 50 minutes from Old San Juan.  

We loved this Airbnb for many reasons.  For one, the patios at this Airbnb are amazing. The front patio has hammocks under a gorgeous tree and the back patio has stunning mountain views.  The hosts at this Airbnb were so kind and helpful as well. Our daughter also loved the swimming pool which is shared. However, we always had it completely to ourselves. When we visited, there was a reservation system in place to only have one family at the pool at a time. Further, this Airbnb is not a resort and allows for a more local experience as the other people at the complex reside there. 

Luquillo and Fjarado are also good areas to stay in while visiting the island. They are far enough away from the city yet close enough for a day trip to Old San Juan and with convenient access to El Yunque and some of the best beaches/beach hiking.  You may also consider staying in Old San Juan if you want to spend more than one day exploring it. 

We hope this guide helps you plan your one day in Old San Juan Puerto Rico.  For more Puerto Rico tips, see our 1 Week in Puerto Rico Itinerary and El Yunque National Rainforest Guide. Anything you’d add to our guide? We’d love to hear your feedback and questions.  Please leave us a comment!

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