Colorful Cities Puerto Rico USA

Exploring Old San Juan, Puerto Rico

San Juan, Puerto Rico wasn’t even on my radar until about a month before we went. I just had no idea it was SO PRETTY!! I’ll be honest, sometimes lots of times I decide to travel somewhere just because I was inspired on Instagram or Pinterest by the way a place looks. And the further I dug into Puerto Rico, the more I wanted to go. Plus, it’s a U.S. territory so you don’t even need a passport, they use dollars, and you can use your phone like normal.

Old San Juan Puerto Rico thisdarlingworld.comOld San Juan Puerto Rico

Old San Juan in particular is an area full of colorful homes, blue cobblestone streets, and incredible food. Did I mention that the weather is basically great all the time? 75 degrees every day we were there, and rain usually comes and goes very quickly if it comes at all. We went in December during a week that Chicago was below freezing so it was beyond perfect.

Old San Juan Puerto Rico

At first I was a little worried that it was more of a beach destination. As many of you know, I don’t like the beach, and neither does my husband. But even if I had just stayed in Old San Juan without going anywhere else, I’d be as happy as the day is long. Colorful adventures and great food is all this girl needs! However, there was plenty to do outside of the city. So next week I’ll be sharing my favorite day trips!

Old San Juan Puerto Rico Old San Juan Puerto Rico Old San Juan Puerto Rico thisdarlingworld.comOld San Juan Puerto Rico thisdarlingworld.comthat’s me thinking about life and what life’s about lol

What I Learned About Old San Juan

We spent 5 glorious days exploring this part of town and absolutely fell in love. Some of the things that stood out to me:

  • The locals are very lively and so so nice, it also helps that we know Spanish. Everyone seems to know English though so no worries!
  • Old San Juan is very clean, walkable, and we felt safe all day long.
  • Hotels in the city center aren’t that expensive.
  • Going out to eat costs as much as it would in Chicago. Of course, there are many options, and you can always opt for cheaper places.
  • Happy hours are the bomb dot com here. It seemed like every place had one and the deals are really good.
  • There is no shortage of perfect doors lol.
  • We went during Christmastime and there was minimal decor, so it didn’t get in the way of me capturing the city as is.

Old San Juan Puerto Rico thisdarlingworld.comOld San Juan Puerto Rico thisdarlingworld.comOld San Juan Puerto Rico thisdarlingworld.comOld San Juan Puerto Rico

Where We Stayed in Puerto Rico 

Hotel Casablanca is right smack in the center of the city! It was a perfect location to explore all day, but rest whenever needed. The service was great, the rooms were clean, and only about $100/night which is a steal in my opinion. If you have more to spend, you can request a room with a balcony. They also have a rooftop with views over the city, and tubs you can jump in (kinda weird) but yes Jorge jumped in one night!

Old San Juan Puerto Rico

Where We Ate 

Like I mentioned, we did not have one bad meal in San Juan. Below are the places I recommend most.

Old San Juan Puerto Rico

Finca Cialitos- We are total cappuccino snobs. We love them from Italy, and compare everything to Italy, and will always compare everything to Italy. However, this place had a damn good cappuccino! So much so that we came back 3 times, and even bought a coffee bag to bring home.

La Bombonera– How great is that name? Order a mallorca with ham and cheese. It’s a sweet bread with powdered sugar (think beignets). They can stuff it with ham or bacon and cheese, they heat it up and flatten it, and it is oddly delicious. Perfect for a cheaper breakfast! OMG, I want one so badly right now.

Old San Juan Puerto Rico thisdarlingworld.comsource:

Cafetería Mallorca– Also had mallorcas here and they were equally good.

Sweets truck- There’s a truck that drives around with a loud speaker selling sweets. Jorge ended up getting a pastry from it (a tornillo), and it was good. When he ordered it, the guy asked if it was “for here or to go” LOL!

Barrachina– They say piña coladas were invented in Puerto Rico, so I had lots. I’m only listing this place because they claim that this is where the piña colada was first made. I had to try it, and it wasn’t good so don’t waste your money. It came out of a slushy machine (first red flag), and then they added rum and you had to mix it. It tasted as flat as you’d imagine. Then Jorge said, and he wanted me to quote him, “it may have been invented here but it was not perfected here.” He’s so deep.

The Mezzanine at St Germaine’s- Hands down my favorite place in the whole area! This is the place with the balconies where my dear camera fell. They have a long happy hour from 4-8pm every freaking day! Half-off a lot of drinks and food (tapas portions). They had martinis half off, and also local Puerto Rican rum drinks. I had my favorite piña colada here, though it wasn’t part of the happy hour, it was still only $6.50! Crazy right?! Everything we ate was SO good, I couldn’t stop ordering food. My favorite dish was the tacos de carnitas. I know, I was surprised too. Best carnitas tacos I’ve ever had. We came here twice, and I can’t wait to go back one day!

Deaverdura- We stopped here to have a traditional Puerto Rican dinner. It’s a small place across the street from Mezzanine. They serve you a variety of traditional dishes on a cutting board shaped like Puerto Rico! One cutting board is more than enough for two people.

Caficultura- We came here for breakfast, and it was pricey but really good. I ordered their famous coconut french toast and they were amazing.

Old San Juan Puerto Rico thisdarlingworld.comsource:

Fruta Fruit- It’s a little stand that sells natural juices from scratch. I made a few stops here to balance out the heavy food I was eating.

Ice cream from street carts– Delicious and cheap coconut ice cream!

El Churry– If you have a car during your trip to Puerto Rico GO. HERE. It’s a food truck 15-20 minutes out of the center, and it’s very popular among locals. Get the “mixto” sandwich.

El Herradero– I couldn’t believe my eyes when I saw that they had “papas locas”. When I visit family in Monterrey MX., it’s a guilty pleasure of mine to always buy a papa loca, which is a huge baked potato mixed with a bunch of good stuff. If you’ve ever been to Canada, it’s a similar idea to poutine. This food truck is parked right next to El Churry. The papa loca was different than Mexico’s, and a little closer to Canada’s. French fries instead of a baked potato, topped with a bunch of unhealthy goodness.

Food trucks on weekends- We didn’t know that there’d be food trucks in Old San Juan on the weekend. We didn’t get to try all the food, but it all looked really good. The trucks are lined up along the waterfront. I did get some churros and they were delish! They reminded me of Spain’s churros as opposed to what we’re used to in the U.S.

Old San Juan Puerto Rico

Can you tell why it’s easy to fall in love with this place? We will definitely be back! It’s a great escape from the brutal Chicago winters.

Old San Juan Puerto Rico

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  • Reply In Between Pictures March 29, 2017 at 4:41 pm

    you tried so many restaurants! Yeah San Juan is more of a town than a beach place. Did you go to El Yunque? I LOVED it there!

    • Reply this darling world March 29, 2017 at 4:46 pm

      I know it was heavily focused on food haha!! We didn’t make it to the rain forest, but it’s okay we’ll be back!

  • Reply Sheila March 30, 2017 at 5:06 am

    I’ve wanted to visit Puerto Rico for so long! I’m in love with the pictures in this post an its colors! Such great tips as well to stay. Can’t wait to travel there!! 🙂

    • Reply this darling world March 31, 2017 at 12:30 pm

      It’s one of those places that you don’t expect to fall in love with, but totally do! I highly recommend a trip there 🙂

  • Reply Christie March 30, 2017 at 11:49 am

    Your pics are so pretty!!! PR wasn’t on my list either until the day I left for PR hahaha. I loved it so much too! I need to go back

    • Reply this darling world March 31, 2017 at 12:31 pm

      Thank you so much!! I’m definitely going to make it a yearly winter destination!

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