Things to Do in Old San Juan, Puerto Rico

Puerto Rico has so much to offer, and it wasn’t even on my radar until about a month before we went. I had no idea it was as beautiful as it is or that there’s so much to do in Old San Juan alone. 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 and they use dollars.

As Puerto Rico continues to rebuild after Hurricane Maria, the island is very much in need of tourism. Old San Juan is up and running and ready to welcome visitors. If it’s been on your list, now is a great time to make it happen. Puerto Rico needs us, and visiting is a great way to contribute to their economy.

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.

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 are all this girl needs! However, there was plenty to do outside of the city.

Read More: Puerto Rico Day Trips

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

Old San Juan: Things to Do and Know 

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. In our book, from all the places we’ve visited so far, Puerto Rico ranks #2 in friendliness (after Ireland).
  • Old San Juan is super clean. I’ll go as far as saying that it’s the cleanest city I’ve seen so far.
  • The old town is very walkable and we felt safe all day long. Walking was my favorite thing to do because I loved taking in the architecture and photographing all the facades.
  • 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. Listing our favorite places below.
  • Happy hours are the bomb dot com here so definitely make time for those. It seemed like every place had one and the deals are really good.
  • We went during Christmastime and there was minimal decor, so it didn’t get in the way of me capturing the city as is in my photos.
  • If you’re a beachgoer then you’re in luck as Puerto Rico is surrounded by some of the world’s most beautiful beaches.

Old San Juan Puerto Rico

Since we aren’t beach people I have no recommendations on where the best beaches in Old San Juan are, but I do know that there are a few nearby beaches to choose from. So, if beaches are your thing, some that you can check out include Playa Peña BeachPlaya El Escambrón, or even Condado Beach though that one is a little further out of the center. 

But if you’re like me and looking to experience a different kind of trip, I’d recommend walking, eating, photographing, and happy houring your way through Old San Juan. Also, don’t leave Puerto Rico without trying a piña colada! I’ll share my favorite place for them below.

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Where to Stay in Old San Juan

Hotel Casablanca is right smack in the center of Old San Juan. 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.

If you prefer something a little more private or lowkey, be sure to check out Airbnb’s in Old San Juan. I love staying at Airbnb’s when possible. I always filter my searches to “superhost” and choose “entire place” to make sure I have the privacy and hosting that I’m paying for.

Old San Juan Puerto Rico

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

Old San Juan Puerto Rico

Breakfast/Brunch Old San Juan

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, heat it, flatten it, and the result is delicious. Perfect for a cheaper breakfast! OMG, I want one so badly right now.

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

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

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Finca Cialitos- And if you’re looking for amazing coffee do not miss Finca Cialitos. 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.

Dinner/Drinks Old San Juan

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 4-8 pm 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. Seriously we spent $100 during happy hour only because we ordered way too much stuff. 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. The food was good and I enjoyed trying and learning about the local cuisine.

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.

Don’t Forget Dessert

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. Good prices and great juices!

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

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

*If you’re visiting during Christmastime make sure to try coquito! It’s like Puerto Rican eggnog. It’s a coconut-based alcoholic drink that cannot be missed. You’ll find them in either the restaurants or the food stands.

Food trucks on weekends- We didn’t know that there’d be food trucks in Old San Juan on the weekends. We didn’t get to try all the food, but it all looked really good. The trucks are lined up along the waterfront. You’ll see all different types of foods ranging from delicious-looking sandwiches to churros. I did try the churros and they were so good. They reminded me of Spain’s churros as opposed to what we’re used to in the U.S.

Old San Juan Puerto Rico

Day Trips from Old San Juan

There are so many day-tripping options from Old San Juan that I made an entire post dedicated to them. You can find that post HERE. You can go caving, check out a bioluminescent bay, or go on a coffee tour to name a few. One of the most popular (and nearest) day trip from Old San Juan is a visit to El Yunque National Forest. Whichever you choose to do, I promise you will not be disappointed with 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 Olivia December 27, 2022 at 2:52 pm

    Booked to reach San Juan on the 6th of Jan 2023. Thanks for the wonderful recommendations. Will definitely be visiting a few of the restaurants and thank you for letting us know about the happy hours :).
    Olivia (Toronto)

    • Reply Lily December 27, 2022 at 2:59 pm

      Wonderful, thanks for reading! You’re going to love Puerto Rico. 🙂

  • Reply Alba June 24, 2019 at 6:22 pm

    Great post! I am a PR local and I agree with you, Barrachina’s Pina Coladas suck. There’s a big debate of where the drink was invented and it’s between Barrachina and a bartender from the Caribe Hilton. The one’s at the Hilton are super good. Next time, try the coconut or the parcha (passion fruit) mojito at La Concha Resort. 😉

    • Reply This Darling World June 24, 2019 at 10:05 pm

      I love this. Thank you for your comment, Alba! I’m glad to see a local agrees 🙂 We will be returning to PR soon and I’ll definitely try your recommendations!

  • Reply Kelly January 28, 2019 at 5:24 am

    I love your photographs and the way you captured the light. We would definitely check out the article if we visited to enjoy some places.

    • Reply This Darling World January 28, 2019 at 1:46 pm

      That means a lot, thank you! I hope you do get to visit soon, it’s an amazing place.

  • 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!

  • 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 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!

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