Puerto Rico: San Juan

In February, my parents were kind enough to come stay with Harrison for a week so Brandon and I could get away for a trip, just the two of us. As you can imagine, getting my parents to agree to spend a week with their adorable grandson took oh-so-much convincing (sarcasm font). I think everyone was happy with this arrangement and felt like they were getting the best end of the bargain.

The trip was prompted by some friends who would be in Puerto Rico for a family wedding. Although we would be meeting up with them later, our first two days on the island were just the two of us. We spent those days in San Juan, fitting in as much sunshine and adventure as we could.

Where We Stayed

After the drive to Portland, a red eye flight to Newark followed by another 4-hour flight to San Juan, and a short taxi ride from the airport (it was super easy to get a taxi at the airport taxi stand at a preset rate based on destination - otherwise we used Uber), The Dreamcatcher was a welcome oasis of calm and relaxation. Located in the residential neighborhood of Ocean Park, the boutique, vegetarian hotel is steps aways from the beach and within easy walking distance of shops and restaurants. Each room is uniquely designed. We stayed in a Sanctuary category room, which have en suite bathrooms including outdoor showers (why are showers so much better outdoors?). Each room in the hotel also has a hammock and includes dedicated space in the onsite community kitchen. Drinks are available for purchase based on an honor system and the onsite restaurant serves a daily vegetarian breakfast and weekly dinners. I loved our stay here and highly recommend The Dreamcatcher for any trip to San Juan.

What We Ate

This will by no means be an exhaustive list of where to eat in San Juan, but are some solid recommendations if you, too, stay in Ocean Park.

Molini’s - After settling into our hotel room, the next order of business was food. Thankfully, home-cooked Puerto Rican food was a short walk away. We both ordered canoita de amarillo - a whole, ripe plantain stuffed with meat and cheese. It was the perfect meal after a long flight and a delicious welcome to the island. Molini’s is a family-owned restaurant serving no thrills, authentic Puerto Rican dishes. We both felt better after this meal.

Lela’s - The following morning, we enjoyed breakfast at Lela’s Eatery after a morning stroll around the neighborhood prompted by waking up unreasonably early after going to bed embarrassingly early for two adults on vacation. Breakfast here was exactly what we both enjoy - I had an acai bowl and Brandon ordered an omelet and we both ordered coffee and mimosas. It was all excellent.

Barrachina - We spent Sunday exploring Old San Juan (more on that below). I will admit I was officially Instagram influenced to make a stop at Barrachina to try the original pina colada. It was delicious and the courtyard was lovely, but it was probably not worth significant extra effort for the experience. It was rather amusing to watch groups of impeccably attired twenty-somethings spend their entire time there taking pictures and not actually drinking the pina coladas they ordered. I’m not saying this is true, but the possibility does exist that maybe we were just too old for this scene.

Areyto - Somehow we managed to rally to eat dinner our final evening in San Juan after our food tour earlier in the day. After walking around and exploring various options, we ended up at Areyto. This chef forward restaurant served elevated, international food with local influences. The cocktails were interesting and the food was fantastic - we especially loved the crab stuffed avocados.

What We Did

The Beach, Of Course - The Dreamcatcher was a short walk to Playa Ocean Park, so it didn’t take us long to get our toes in the sand our first day here. Whatever you like in a beach - seclusion, great restaurants, lots of activities, no activities - you can find the perfect spot in Puerto Rico. In San Juan, we loved staying somewhere we could easily access the beach, no car needed. Our hotel even had beach items, like chairs and coolers, that could be borrowed. If you are based in San Juan for your entire trip, you may consider a day trip to a more far flung beach for a change of pace. Whatever you decide, no trip to Puerto Rico is complete without some time on the beach.

Old San Juan Food Tour - You know I love a good food tour. In fact, this is one of my favorite ways to get to know a new city. For our brief time in San Juan, this was a must-do activity for us. We booked the Classic Old San Juan Food Tour with Flavors of San Juan. With five stops, including multiple tastes and one cocktail, we were so full of delicious Puerto Rican food by the end of the tour. We also got an interesting overview of the history of the city and island (did you know that Puerto Rico used to be the name of the city and San Juan used to be the name of the island?) from our excellent and engaging guide, Itzel. My only complaint was the pacing of the tour, which I know is always a challenge. At some spots we felt rushed and at others we felt like we were there for far too long. Regardless, I highly recommend this tour, especially if you are short on time. This was some of the best food we had the entire trip. Another company that comes highly recommended for food tours is Spoon.

Our first stop was at Cuatro Sombras for delicious Puerto Rican coffee in the form of a cortadito. As we sipped, we learned about the coffee production on the island.

The coffee was paired with the croissant sandwich, which had ham, provolone, and guava butter. The guava butter made the sandwich.

Next we got to try passionfruit popsicles (passionfruit may be a new favorite of mine) from Senor Paleta while we learned more about the history of San Juan.

Seriously, Itzel was such a great guide and had so much knowledge about and passion for the history of her home.

Our next food stop was Cafe El Punto, where we tried alcapurrias and this delightful grouper ceviche

We also had enough time at this stop to order one of their excellent mojitos. Mine was passion fruit, of course.

In addition to eating lots of great food, we also learned more about Puerto Rico. This is the famous “umbrella street” which leads to the governor’s house. Unfortunately, it was umbrella free during our visit.

Some of these cobblestones are hundreds of years old

The next stop was Triana, which is known for both authentic Puerto Rican food and for flamenco shows. Here, we got to make our own mofongo.

This is a classic dish of fried, mashed plantains usually paired with some type of meat, in this case stewed chicken. This was the best mofongo we had the entire trip.

All of this yumminess was paired with a classic pina colada.

Our final stop was Chocobar. We were lucky that our tour included this spot, because there is usually a long wait to get in. As the name suggests, here is the place for all things chocolate. We enjoyed chocolate quesitos. Itzel shared that a local favorite is hot chocolate with a side of cheese. I still haven’t tried that combo.

Castillo San Felipe del Morro - The history of San Juan and Puerto Rico is fascinating. We started our Sunday in Old San Juan exploring del Morro, one of the two forts that is a part of the San Juan National Historic Site. With more time, we would have loved to explore more of the historic sites and walk the length of Paseo del Morro - a walking trail along the edge of Old San Juan with stunning ocean views.

Ole Puerto Rico - I spent a large amount of this trip missing my son, so it’s no surprise I was looking for the perfect souvenir. As soon as we passed Ole Puerto Rico I knew we had to go back and get our hat loving son a handmade hat. If he had been there, it would have been custom fit to his head. As it was, I erred on the large size and the ladies in the shop took the time to add an extra layer onto the inside of the hat that will make it more adjustable. I picked out the exact ribbon I wanted and watched as it was carefully added to the hat. I love buying things that both support small, local businesses and that will be treasured (hopefully) for years to come. This was the perfect gift for Harrison.

We loved our time in San Juan and only wish we could have stayed longer. Thankfully, there were more adventures in store. After two nights in the city, we drove through the central mountains to pick up our friends and then headed west to Cabo Rojo.