4 Days in Old San Juan Puerto Rico

Imagine stepping into a postcard-perfect world of colorful facades, cobblestone streets, and the tantalizing scent of Puerto Rican cuisine wafting through the air. Welcome to Old San Juan, a historic district that effortlessly blends colonial charm with a vibrant Caribbean spirit. Christopher and I just recently went on a four-day adventure through the sun-soaked streets, indulging in the delectable flavors and basking in the rich history of this captivating gem of Puerto Rico.

We flew in on May 28th and flew out on June 2nd, If you plan on visiting during this time or any of the summer months, be prepared to sweat. It was on average 90-98 degrees every day we were there with a UV of about 10. It didn’t take long to overheat and burn in the hot sun. We spent most of our day eating and lounging by the pool to stay cool, and then we did most of our exploring at night when it was cooler.

One more tip to note: Old San Juan is also a cruise port, so if you are visiting during any of the days that the cruises stop in, be prepared for the town to be crazy busy. Most of the days were quiet and we had no problem getting into any restaurants or bars, but the one day we were there, one of the huge Norwegian cruise boats stopped in port for the day, and we were not able to find anywhere to eat lunch as all of the town was mobbed by everyone on the cruise. We ended up eating and relaxing at our hotel that day to get away from all the chaos.

Getting There:

Arrival and Immersion As our plane touched down at SJU airport, the excitement was palpable. Opting for convenience, we hopped into an Uber and embarked on a short journey to Old San Juan. The ride was smooth, allowing us to catch glimpses of lush palm trees and sparkling ocean views along the way.

Where We Stayed:

Our accommodation for the trip was the enchanting Palacio Provincial, a beautifully restored boutique hotel nestled within the heart of Old San Juan. The hotel's exquisite colonial architecture transported us back in time while providing modern comforts. With its prime location, we were just steps away from the charming streets, bustling markets, and vibrant nightlife that awaited us.

This hotel was beautiful and it had everything we needed within the hotel to make it a perfect trip. The hotel is mainly all open to the outdoors, aside from your room. The hotel had an outdoor restaurant the Consular Restaurant & Bar, that served breakfast, lunch, and dinner, including some of the most delicious pizzas I have ever had. On the other side of the ground level, they had a beautiful courtyard that had plenty of seating options as well as a beautiful water fountain. We spent most of our nights relaxing out here before dinner and it was perfect.

Our room was on the smaller side, but it had everything we needed. It was clean and stylish and had a nice walk-in shower, fridge and safe.

I would have to say the best part of this hotel hands down is the rooftop pool and the views. We visited from Sunday-Thursday and every day that we went up to the hotel rooftop pool there were maybe only one or two other couples up there. It was perfect and felt very private even though we were in the middle of the city.

They have a rooftop infinity pool with views of the Old San Juan Bay, it was the perfect way to cool off from the heat and still get a taste of the Old Town. We spent most of our days relaxing and swimming up on the roof when it was too hot to walk around.

What We Did:

We spent most of our days during this trip walking the streets of Old San Juan and taking in the culture, smells, and sights. There are so many great photo opportunities around Old San Juan that make it a photographer’s dream destination.

Unfortunately, while we were there, we were having some camera troubles and we were not able to take as many photos as we would have liked, but we hope to return one day to make up for it!

We happened to be visiting Old San Juan during my Birthday, so for the day we took a trip to the Royal Sonesta resort, where we were able to book a private poolside cabana for the day. The cabana was great, when you arrive, you are escorted out to your private cabana where you meet your designated server for the day. Included in the VIP cabana package, you get a free bottle of Cava Sparkling Wine, a massive fruit platter, and 4 bottles of ice-cold water, it was totally worth the price for a little VIP treatment for the day. The Royal Sonesta was great, they had one massive pool with a swim-up bar and hot tub, a small beachfront restaurant, gym, spa, and beach access. I booked our VIP cabana through Resort Pass and the process was so simple, it cost us $306 for the day.

What We Ate:

As a vegetarian, I was worried that there wouldn’t be many vegetarian options around Old San Juan, but I was pleasantly surprised to find so many different and delicious options that were available. These are all the places we ate while visiting:

Breakfast:

Consular Restaurant & Bar: We had breakfast most days here as it was convenient and the food was delicious.

La Carreta Mercado: La Carreta was delicious and the perfect breakfast option for us one morning. We both had freshly squeezed juice, and I had the fried eggs, with sweetbread and papas fritas with a side of aioli dipping sauce. Christopher had the eggs benedict with avocado, poached salmon, and a side of papas fritas. The meal was delicious and the staff was so friendly.

Café Cuatro Estaciones: This was a little stand located on the corner by our hotel that served hot coffee, tea and pastries all day.

Lunch:

Consular Restaurant & Bar: We had lunch here a few times since it was so convenient to grab a pizza and a drink and bring it up to the rooftop pool. Their pizza and pasta braves were delicious, Christopher also had their Tuna Tartar “Montaditos” which he loved.

La Madre: This was hands down the best lunch we had while we were there. La Madre is a small authentic Mexican Restaurant that was a short walk from our hotel. They only serve their brunch menu during the day but the food and the atmosphere were fantastic. We had to wait about 40 minutes to get in as it is a very small restaurant with limited seating but it was totally worth the wait. Christopher had the Octopus Tacos and said they were one of the best he’s ever had. I had the Sopas Huerto which came with two Sopas, beans, stir-fried veggies, cilantro cream, cheese, sauce, and a potato hash. I can’t even tell you how delicious this was, Christopher even ate half of mine because it was that good. We also got a side of sweet potato fries and a chipotle aioli sauce for dipping and two Modelo Negros. This lunch was perfect.

Dinner:

La Ó Pizza and Tapas: This restaurant was so delicious we ate there twice. They had so many great vegetarian options for me to pick from and they were all equally divine. The first night we ate there, we split the arancini for an appetizer, and I had the Vegetarian San Benito pizza with caramelized onions and goat cheese, ugh it was so good. Christopher had the San Celedonio pizza with smoked salmon and capers. Both of the pizzas were the perfect personal size so we were not too stuffed. To drink, I had a glass of their sangria and Christopher had the Lavender She Rose which was topped off with a smoking sprig of lavender.

The second time we ate there, we started off with the arancini again as it was sooo delicious, I had the Bell Peppers Stuffed With Zucchini as my main along with the side of risotto and sauteed vegetables. Christopher had the seafood Santa Paula pizza, which he said was not as good as the pizza he had the first night. I would highly recommend this restaurant if you are looking for some great vegetarian or pizza options.

Il Bacaro Venezia: Il Bacaro was a pasta lovers dream and perfect for me as a vegetarian. This restaurant had so many pasta dishes to choose and the atmosphere was great. They had a big crazy bar and a ton of cool artwork on the walls which we loved. When we sat down, Chris was a little bummed that it seemed like the only thing on the menu to eat was pasta, but then when our server came over, she had a handful of other specials to read off which included a lamb chop, which Chris ended up ordering, a Salmon special and more. We started off with the Tomato and Burrata platter with pesto, and I had the arrabiata spaghetti for my main. The food was fantastic and perfectly satisfied my pasta craving. The food, drinks and atmosphere here were all 5 stars.

Azalea: After eating all the pasta and pizza the past few days, we wanted to opt for something a little different for dinner this night. We found this Latin Asian restaurant and made a reservation online. The food and atmosphere here were great and I would say this felt like one of the more romantic dining options we had. We were seated at a small two-person table with a candle and the atmosphere here was a little dark and moody which was nice for the date night vibes. We started with a bowl of the Edamame to share which was cooked perfectly. For our dinner, Christopher had a mix of three sushi rolls which he said were all fresh and tasty. I was happily surprised to learn that they could do the Pad Thai Entry vegetarian, putting the scallops on the side for Chris to eat with his meal. I have to say, this was one of the better Pad Thai dishes I had in my lifetime, it was perfectly sweet and savory at the same time with a mix of a ton of fresh veggies and peanuts. This dish was huge so it was enough for both of us to share, with it I also had an order of avocado rolls, which weren’t the best I’ve ever had but still good.

Dessert & Drinks:

La Mamma Del Gelato: We had to make sure we stopped here at least once on our trip as we had seen this place all over the travel guides for Old San Juan. This was one of the cutest old-style gelato shops I have seen and the gelato was SO GOOD. We were happy to see that this place was one of the few places that stayed open past 11pm so we decided to treat ourselves to a late-night snack. They had so many flavors to choose from and none of them disappointed. I would have come here just for the atmosphere alone, you must come here at least once during your stay!

La Factoria: La Factoria is among one of the world’s top 50 bars and I could see why after one visit. We decided to go out the night before my birthday for a little celebration and found ourselves a great spot at the main bar here. La Factoria is made up of 6 bars that have secret passages that lead to each one, it was just as much fun to be there and to search for the bars as it was to hang out and drink at them. We had so much fun talking with the bartenders, we ended up staying there for almost 3 hours at the bar drinking and talking, they even sang me happy birthday (In English and Spanish) and gave me and Christopher a glass of champagne to toast, it was perfect. All of the drinks were outstanding, but I would have to say this was one of the best Aperol spritzes I ever had (and I may have had a few too many).

La Grieta: I think this Mezcal bar was SO underrated for how cool it actually was. Christopher and I loved it here, La Grieta is part of the La Madre group and is attached down the alley from La Madre which I mentioned above. This was one of our favorite bars that we visited as the atmosphere was spot-on with the music and decor. Not to mention the drinks were great and the bartenders were super friendly. This bar is a must-revisit for us.