Skip to content

A Guide to Old San Juan in 24 hours!

A Guide to Old San Juan in 24 hours!

A Guide to Old San Juan in 24 hours!

After a cold and dark winter period I booked flights to Puerto Rico to explore Old San Juan and El Yunque. This was my first trip to Puerto Rico and the only reason I picked this destination was because as an immigrant, it still constitutes as U.S.A so no passport is needed! After spending only one day however, I immediately regretted it, I wished I had stayed longer!

However, I did pack a lot of activities, and it is possible due to how small and explorable Old San Juan is. It is only roughly 7 square blocks and so there is a lot to do.

How to get there?

There are many airlines which provide routes to San Juan, some of which are more affordable than others. I went via Southwest due to my elite status and numerous points which I have accumulated thanks to my previous travels, but I saw many other airlines including Spirit, Frontier, Delta, American, United and JetBlue. The flight went relatively smoothly, and it is good way to practice your Spanish with the other passengers and the flight attendants. I was also able to catch up on some movies on the 5-5.5 hr flight. Once you start descending, you will start to see the wonderful site of the Caribbean and the coast.

After that you get a good idea of what the weather and general vibe of the island and the day!

Luis Muñoz Marín International Airport

Once arriving at the airport, you get the sense that you are in the tropics! It is warm, humid and crowded, definitely not like the mainland Airports!

As my itinerary would involve going to El Yunque for a few nights after San Juan, I had booked a car with National for 4 days in total which came to $460. I had managed to forego the collision waiver and roadside assistance as I paid with my Chase Sapphire Reserve but needed to pay for liability insurance. I was definitely paying for the convenience to pick up the car from the airport and hence the higher price, but as Uber is meant to difficult to get in Puerto Rico and in the airport, I wanted to pick up the car and start exploring! I rented with National and utilized the Emerald Membership that I get with being a Chase Sapphire Reserve cardholder.

Once landing at around 1pm, and after baggage claim, the Elite Emerald service allowed me to pick up the car and be in Old San Juan by 3pm, leaving 24 hours to explore Old San Juan!

Airbnb

Courtyard view from my Airbnb

I utilized an excellent Chase Offer where if I paid for an Airbnb I would get 5% back in Chase credit. This along with 3 points per every dollar in the form of Chase Ultimate points proved very useful!

I really like Airbnb for its design in meeting locals and flexibility in location as well as its more affordable rates. My host did a great job helping me get to the apartment, finding a cheap and safe place to park the rental car and advising local restaurants to eat.

Communal area of the Airbnb

Dining

My host recommended Raices which had authentic Puerto Rican food and was delicious. I actually went there twice, because it was tried and tested as well as close to the Airbnb. I went for the Mahi Mahi Creole Style Stuffed with Shrimp in Garlic Sauce and stuffed Avocado as well as sides such as fried cheese (that can never go wrong!) and a platter of friend foods stuffed with different fillings.

I didn’t get to really try any other foods in the city, as I was happy with this restaurant and because of limited time. But the way the trip went, I would gladly go back for more food and sights!

Evening walk

For the best place to have an evening walk, I would recommend walking down Paseo de la Princesa which is north of La Puntilla. Along this street you can treat yourself with savory and sweet snacks from multiple vendors. As you continue you will pass La Princesa, a historic landmark which was once a prison and now is the Puerto Rico Tourism Company’s headquarters.

As you continue walking, you’ll end up at the Fuente Raices, a beautiful fountain. From there you will get some lovely pictures of the sunset and water as well as soak up the atmosphere of the evening vibe.

There is a passageway from the fountain that takes you along the waterfront outside the walls of the city, but this gate was blocked off when I tried to go there. For that reason I headed back towards the Airbnb and walked uphill along Calle San Jose to experience the vibe of the city on the Saturday night. I walked up to Castillo San Felipe Del Morro which is pretty breathtaking even in the dark and considering I travelled from the cold Midwest, was a nice evening stroll, without being too cold or hot. There’s a lot to do nightlife in Old San Juan and my Airbnb host even offered to meet up, but as I was only in the city for 24 hours, I wanted to go to sleep early and wake up early to get as much sites as possible

Sunrise

For the sunrise there are lots of places to go, you can walk to either the grounds of Castillo San Felipe Del Morro or you can go to Castillo de San Cristobal, as I wanted to walk towards the Eastern part of Old San Juan. During this time, the weather is comfortable and there are very few people around which makes picture taking and exploring very comfortable.

Paseo del Morro

I decided to walk along the Paseo del Morro. This trail follows masonry walls dating back to the 1630s that surround the city of Old San Juan. It was a maintenance road for the west section of the city walls. The trail clings to the city wall from the San Juan Gate to Castillo San Felipe del Morro along the entrance to the San Juan Bay. The views of the walls as well as the ocean are beautiful and I would definitely recommend it once the sun is out and you have enjoyed the sunrise.

Entrance

In order to get access to the trail I went via Calle de Tetuan which grants access to Capilla del Santo Cristo de la Salud which is a Chapel. Along the way you will come across La Casa Estrecha which is “The narrow house” which was originally an alleyway and is now a house as well as other beautiful architecture. This was quite popular and I managed to eavesdrop on the tour which was going on whilst I was exploring. For more information, see this website.

Calle de Tetuan. The Yellow building is the smallest house in the Western Hemisphere! La Casa Estrecha

From the chapel you can access Calle del Cristo, which is how we accessed Puerta de San Juan to get to the trail.

On the way is Parque Las Palomas, a park dedicated to pigeons where a vendor is selling bird food. You can enjoy the park as well as the view.

Posed for the picture as quickly as possible…didn’t want to ruin the white shirt!

After the park you will pass on your left as you head up hill, Calle de la Fortaleza, which is quite an iconic site especially for the instagrammers. Usually they have umbrellas during summer, covering the street from the sky but at the time they had a big Puerto Rico flag. There was heavy security as La Fortaleza is where the governor lives in essentially what is the White House equivalent.

From there you can keep going till Caleta de San Juan where you can turn to Puerta de San Juan which was locked at night historically. If we were trapped outside, you had to wait the entire night!

Along the trail you can admire the ocean, the walls and there is a set up to look after the numerous cats on the trail which is funded by charities. You can also spot other wildlife creatures.

As the trail turns east you will come to some steps that lead to Castillo San Felipe Del Morro, which I had visited the evening before. However with the sun out and the Sunday crowd, the atmosphere is so much better during the day.

By the castle there is the Visual Arts institution (yellow/orange building) as well as the Cuartel de Ballajá, which was built from to house the Spanish and Puerto Rican regiments in Old San Juan (the second floor is the Museo de Las Americas).

Once you are finished, make sure to visit the Cementerio Santa Maria Magdalena de Pazzi. Built overlooking the ocean in Old San Juan, this beautiful cemetery is located amid two of the island’s busiest attractions, the El Morro fort and Castillo San Cristóbal. 

By this point, refresh yourself with coconut water and the vendor by the cemetery will even cut up the coconut afterwards so you can the coconut meat. At this point you can enjoy the view as you walk along Calle Norzagaray with the Ocean and La Perla to your left and buildings such as the Institute of Puerto Rican Culture and Museum of Art and History to your right. If you did choose to head south back to Vajo de Manglar all the streets and buildings are beautiful and you can walk around this mainly residential area. If you were to follow Calle Norzagaray it would eventually take you to Castillo de San Cristobal.

By this point I was getting hungry and it was time to start driving to the part of the journey, El Yunque to a Bed and Breakfast called Casa Flamboyant which is on the Southern part of the tropical rain forest. I’ll have a more comprehensive review on that coming up soon.

So this is my whirlwind tour of Old San Juan in 24 hours. Plenty to see despite such a small area, I will certainly be back. Old San Juan is a place where the sites and architecture are free to enjoy and walk around. You can get a very cheap Airbnb and flights to get there. The only thing I would recommend looking into is transport from the airport to Old San Juan. I rented a car but mainly because I was limited in time. That may be something that I will look into next time.

What are your favorite sites in Old San Juan and where else in San Juan would you recommend? All comments are appreciated!

Enjoy Penny Pinchers!