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Winter Escape: San Juan, Puerto Rico

  • Writer: Anne Lam Music
    Anne Lam Music
  • Dec 14, 2025
  • 7 min read

Welcome to another travel blog post! Today, I'm going to walk you through everything I did, saw, and ate in San Juan, the capital of Puerto Rico. This was a very last-minute trip. We booked it two weeks before flying out, and I literally planned the entire trip in about an hour.




DAY 1:


The first day was mostly just arrival and check-in. We had a MAJOR inconvenience at the Toronto airport, since we had to check our luggage in ourselves using the automatic check-in lanes. However, many weren't working, and there weren't many staff members checking luggage manually. When we tried to queue for manual check-in, we were actually turned away and told to try the self-service kiosks again. It made absolutely no sense whatsoever. After more than an hour of trying to check our luggage, we were finally told to ask an assistant to do the manual check-in for us, which is exactly what we tried to do earlier... So yeah, it didn't make any sense, and caused so much unnecessary stress.


Anyway, we stayed in Old San Juan, which was super colourful and quaint!! So cute!!



We stayed at Casa Las Ruinas, which was a little difficult to find at first since there was no sign, but luckily, they sent us check-in instructions ahead of time that were very easy to follow. The room came with all the basic necessities, and the open courtyard was such a vibe. After checking in, we started walking around, seeing what was near our accommodation. We saw many boutiques and even a bookstore, where I later bought two books. I've even already finished one of them. It's called Sanctuary, and it was a great read. In short, the book is set in a near-future United States, where everyone is chipped, therefore making it much more difficult for illegal immigrants to stay there, undocumented. The story follows a family who has fake chips installed, as they attempt to escape Vermont, where deportation crackdowns are increasing.



For dinner, we went to Barrachina, specifically to try the piña colada. Apparently, it's where the drink originated, so it would have been silly to go there and not try it. I was surprised because they really didn't skimp on the alcohol, and the texture was very creamy. It was almost like a milkshake. As for the food, I ordered mahi-mahi, and my partner had steak. To be honest, the food wasn't anything spectacular, but it was fine since we were mainly there for the piña colada.



Afterward, we walked around the area a bit more before returning to our accommodation to rest for the night.




DAY 2:


We spent the second day mainly exploring Old San Juan. First, we had breakfast at St. Germain Bistro Bar. To be honest, we didn't like it very much, because many items on the menu weren't even available. Because of this, we had to keep changing our order and waited a long time. In the end, I ordered a Mallorca sandwich, which was okay. My partner ordered a fairly standard breakfast: potatoes, eggs, bacon, and toast. Again, the food wasn't anything special.




I wanted to visit the cathedral first, but there was some kind of service going on, and we couldn't go in. So, we visited other landmarks before returning to the cathedral later. One of the things we saw was a sculpture called La Rogativa. It's a sculpture of the former Bishop of San Juan and three women with torches. According to legend, the women of San Juan held a religious procession one night in 1797 with torches, ringing bells and singing hymns, which tricked British Lieutenant General Abercromby into believing that reinforcements were flooding the city. Fearing he would be outnumbered, Abercromby and his fleet withdrew.




We also visited the Puerta de San Juan, the last vestige of the original gates that controlled access to the walled city of Old San Juan. Built around 1635, this gate served as a formal and symbolic entrance for important visitors, including new governors and bishops arriving by sea. I love the Latin inscription: Benedictus qui venit in nomine domini.



That day, the heat was sweltering, and we were sweating profusely. There was a slight breeze by the water, but we were both drenched in sweat.




We also visited the Fuente Raíces (Roots Fountain), which celebrates the island's Taíno, African, and Spanish heritage with bronze figures. It was built to commemorate the 500th anniversary of the discovery of America.



After walking along Paseo de la Princesa, we decided to head back to the cathedral to see if we could go inside this time. And luckily, it was open! I was really looking forward to visiting it, as it houses the remains of the Spanish explorer, Juan Ponce de León.





After visiting the cathedral, we went to a bar called La Factoría. This was another place I was eager to visit, as it was included on the list of the 50 best bars in the world, and also appeared in the music video for "Despacito." Of all the restaurants and bars we visited during our stay in San Juan, La Factoría had the most original and unique cocktails. Our bartender was also super nice and attentive.




For dinner, we went to a restaurant called The Cave. The food was quite good, and the service was excellent. We ordered ham croquettes, salad, and Cuban montaditos. I think the ham croquettes were my favorite of the three.



After dinner, we went to a place called Drunken Cookies. I saw it the day before, and made a mental note to visit it. Basically, they give you a free mini-shot with the purchase of a cookie.



All the cookies looked amazing. We opted for a churro-filled cookie and a Kahlúa pipette. The coffee flavor of the Kahlúa paired perfectly with the cookie.





DAY 3:


We started the morning with breakfast at Caleta, right across from the cathedral we visited the previous day. The food was fantastic, much better than in St. Germain. However, I didn't like that they didn't advertise that this place didn't accept cash. When I travel, I usually pay only in cash and avoid using cards. That's why I didn't like that there wasn't any sign indicating that this place only accepted card. After breakfast, we went back to our accommodation to change and get ready for snorkelling!



For snorkelling, we had to go to Escambrón Beach. It was my first time snorkelling, and honestly, it wasn't tiring at all, but it was very uncomfortable. Even so, I'm glad we did it, because we were able to see several sea turtles, which were so cute!



After snorkelling, we showered and changed again at our accommodation and spent the afternoon strolling around and buying some souvenirs. We stopped at a restaurant for lunch. I don't remember the name. We thought the food would be good, because it was absolutely packed. That's usually a good sign. However, it turned out to be the worst meal of the entire trip. I ordered fish tacos, but they were bland and barely contained any fish. They were filled with cabbage and had practically no sauce.



Later, for dinner, we decided to return to The Cave. This time, we sat inside the restaurant. I loved the atmosphere. SUCH a vibe! We ordered the ham croquettes again, as they were delicious last time, but this time we also ordered a pasta dish, which was very tasty. The sauce was quite thick, though, so we got full very quickly.




DAY 4:


We spent our fourth day here continuing to explore Old San Juan, since we hadn't yet had time to visit the two historic forts: El Morro and San Cristóbal. The good thing is that if you buy a ticket to visit one of them, it also includes the other, as long as you visit within 24 hours. On the way to the forts, we stopped at the "I Love San Juan" sign to take some pictures, and I found it very funny that my partner was wearing his "I love poutine" t-shirt from Montréal.



First, we visited San Cristóbal. It had many intricate tunnels, ramps, batteries, sentry boxes, and a complex defensive structure. The views were also magnificent!



Before visiting El Morro, we stopped for lunch at a place called La Madre. I wish we had discovered this restaurant sooner, because it turned out to be my favorite restaurant during our entire stay in San Juan. The service was excellent, and the food was absolutely delicious! We ordered the duck quesadillas, which were incredible. We also ordered grilled chicken and tamale in a rich and creamy avocado sauce. I LOVED both dishes.



On the way to El Morro, we stopped at the Church of San Francis of Assisi. It's the second-oldest church in Puerto Rico, and one of the oldest buildings in San Juan.



There was a very long road leading to El Morro, and although the heat was relentless, the walk to the fort was very peaceful.



Needless to say, we walked a lot that day. We also found this wall with pieces of art that encourage you to take pictures.



For dinner, we ate at an Italian restaurant called Bacaro. The food and portions were excellent. I ordered the mushroom risotto, and my partner ordered the pasta alla amatriciana. Both were delicious! Since the menu was written in Italian, I started to mix up my Spanish with the Italian, but I think that's quite normal for multilingual people.




DAY 5:


On our last day in San Juan, we went to Café Luna for breakfast. All the specialty coffees looked very interesting, and I ended up ordering one with lavender. It was a such nice touch. I ordered the pancakes filled with melted cream cheese. They were delicious, but very filling. The service was a bit slow, but the staff was friendly.



After breakfast, we went to a museum with a free art exhibit. I don't really know much about art, but I found the pieces beautiful and full of detail.



We bought more souvenirs and strolled around for a while before returning to our accommodation to change and get ready for our night-time kayaking experience. For this, we had to go to Fajardo. Why night kayaking? Because we would be kayaking in a bioluminescent bay. Honestly, the experience was a bit dangerous, but it was AMAZING to see the bioluminescence and even hold a glowing jellyfish in my own, bare hands!! It was extremely dark, so I couldn't record anything, but that also allowed me to immerse myself more in the experience instead of worrying about documenting everything.




When we returned to Old San Juan, it was already very late, so for dinner we just grabbed some hot dogs and went to sleep.




And that's it! If you've made it all the way until the end here, thank you SO MUCH for reading. Don't forget, you can also check out my YouTube video of this trip, where you can see more actual footage and also hear me speak Spanish (:


Take care, and see you in the next post!


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