Old San Juan Puerto Rico

Happy 2019! I’m still recovering from our trip over the holidays. It’s nice to be back home, getting back into my routine and setting intentions for the new year. Although, I’m already getting antsy for our next trip – which hasn’t been planned yet! 

Over the holidays, Paul and I went on a Caribbean cruise which departed out of Puerto Rico. We’ve been once before, but enjoyed the city so much more this time around. 



Old San Juan Puerto Rico

Old San Juan is a vibrant town full of colorful buildings and delicious food. Puerto Rican’s are really proud of their culture and traditions and that rings true in everything they do. I love walking down the streets and hearing Latin music blaring through the speakers. I love smelling the spices and eating the fresh produce found in all of their food. San Juan is just a really cool, really fun place to explore. 


We arrived Friday afternoon and immediately after checking into our hotel we headed to Old San Juan. Old San Juan is the oldest city in the US (and the US territories), as it was settled by the Spanish in 1521. 


24 Hours Exploring Old San Juan Puerto Rico

I was dying to see the colorful umbrellas on Fortaleza street. The Paseo de Sombrillas is meant to fill the viewer with joy and pay tribute to Puerto Rico. 

Find the Paseo de Sombrillas at: 65-55 Calle Fortaleza


Old San Juan Puerto Rico

After the umbrella’s we headed over to the PR Door. This building is painted with a mural of the Puerto Rican people and their flag. 

Find the PR Door at: 58,50 Calle San José


For appetizers we decided to try Verde Mesa. It’s a very small, cozy space serving globally inspired food with a Puerto Rican flare. They use local ingredients and are vegetarian friendly. They don’t take reservations, so we were lucky there were only a dozen people in line in ahead of us. We waited about 20 minutes before we were seated. The line out the door was literally down the block. I imagine those people waited at least an hour! 

Find Verde Mesa at: 107 Calle Tetuan Esq, Calle San José

Of course, pre-dinner drinks are a MUST so we headed to the rooftop bar at Mezzanine. It was raining, so we had to sit at the indoor bar, but the windows and doors were open and the breeze was amazing. 

Find Mezzanine at: 156 3rd Floor, Calle Sol

We wandered across the street for dinner at Deaverdura. This local spot slings homemade Puerto Rican food. They have no menu, the waiter approached our table and recited their offerings. I went with the vegetarian plate, which included beans & rice, salad, and a grilled vegetable stuffed avocado. 

Find Deaverdura at: 200 Calle Sol



24 Hours Exploring Old San Juan Puerto Rico

Saturday morning we headed out bright and early, as we had to be on the cruise ship by 5pm. My blood type is coffee, so we went straight to Cafe Cuatro Sombras for a Cortidito (amazing), an iced latte, and veggie quiche. This cafe had a nice airy open vibe and the coffee was so tasty! 

Find Cafe Cautro Sombras at: 259 Calle Recinto Sur

Old San Juan Puerto Rico

One of my favorite things about Old San Juan is all of the colorful buildings. Lime green, coral, sea blue, and even purple painted facades are on every street. We wandered around for quite awhile just enjoying the architecture and the quiet morning.


Old San Juan Puerto Rico

Paul’s sister joined us for lunch… aka, Pina Coladas! We wet to Barrachina, which is the home of the original Pina Colada. They are made alcohol free but the bartender had a heavy pour on the rum! We sat at the bar in the outdoor courtyard which was really nice. 

Find Barrachina at: 104 Calle Fortaleza

Old San Juan Puerto Rico

Of course, I couldn’t leave OSJ without a fresh fruit popsicle, so we made our last stop at Señor Paleta for a strawberry popsicle. Bonus points, not only was it tasty & refreshing, but it looked oh-so-cute posing in front of the colorful buildings! 

Find Señor Paleta at: 153 Calle de Tetuan

On our previous trip to San Juan, we toured Castillo San Cristóbal, an old Spanish fort, but didn’t have a chance to make it back there this time around. 

Find Castillo San Cristóbal at: 501 Calle Norzagaray

San Juan is such a warm & vibrant city. Everyone we encountered was so kind & helpful and we truly enjoyed our short time in Puerto Rico. 

Old San Juan Puerto Rico Old San Juan Puerto Rico Old San Juan Puerto Rico Old San Juan Puerto Rico Old San Juan Puerto Rico

24 Hours Exploring Old San Juan Puerto Rico

Old San Juan Puerto Rico

Why not PIN for later?

How did you spend your holidays?! 


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  • Emily Keen January 14, 2019 at 7:09 pm

    Great post, Kimber! Loved the info about where you all ate and drank at. And, beautiful photos! Also, crazy — my bloodtype is coffee, too! Hahaha

    • aholidayaway@gmail.com January 16, 2019 at 4:46 pm

      Thanks so much, Emily! And, I’m happy to hear I’m not the only one with coffee running through my veins 🙂