caribbean latin america travel usa

What to See + Do in Old San Juan

I know. Everybody goes on and on about Viejo San Juan. I let it roll off as yet another Instagram tourist trap, but I’m glad I went anyway. It is so, so beautiful, with winding cobblestone streets and whimsical cafés tucked into every corner. After this first trip to Puerto Rico, I must admit that Old San Juan is definitely my favorite neighborhood in the capital city, and I plan to stay there longer next time. We did many fun things in Old San Juan, and even left Dorado to come back to the city for our last two days on the island. Here are 7 must-dos in Old San Juan!

1 // Old San Juan Free Walking Tour

Before you even go anywhere else, try to book the Old San Juan Free Walking Tour for your first or second day. I recommend booking in advance by email, which you can find on their Facebook page. It’s offered in English and Spanish. Our guide, Sara, was so knowledgeable and gave valuable insider tips on what to see, do, and eat in the city and on the island as a whole. It’s about 2 hours on foot, and you get to see many aspects of Puerto Rican history. It is 1000% worth the time and your guide will surely deserve a tip for tour’s high quality. I’ve been on many of these before Sara’s, and it ranked very high on my list. Definitely one of the best I’ve ever been on!

2 // Stay at Casablanca Hotel

This. Place.
Y’all.
You have to stay here. The decor is from centuries past intermingled with modern touches. The staff are so friendly, personable, and accommodating. The only aspect of our stay that we found lacking was the food, but that can be overlooked for the beauty of the place, the comfort of the beds, and the five-star location. We only booked this place for a night on Expedia because we had a gap in our itinerary, but I wish it had been longer! From the lobby to the rooftop complete with bathtubs (!), this place is a winner. I’ll let the photos speak for themselves.

3 // Visit El Morro

One of the reasons to go on the Old San Juan Free Walking Tour early in your trip is so your guide can tell you what to see for the rest of it! Sara, along with many other locals that wanted to help our a couple of Tennessee gals, recommended El Morro. Its official name is the Castillo San Felipe del Morro, so you can see why the name is commonly shortened. We paid $7 to to enter and see the colonial fort. It reminded me a lot of the Citadel I saw while in Haiti. You can also use your entry ticket to access El Castillo San Cristobal within a certain time frame. We didn’t this trip, but I definitely will next time! I love how buildings like these from history transform visitors to another time. Fun fact: these monuments are technically part of the U.S. National Parks. You can check out ticket prices and other entry info here!

4 // Tour El Museo de las Américas

From El Morro, the iconic Museo de las Américas is a short walk away. Each exhibit is in a room, and you access those rooms through an outdoor walkway on the second floor of a plaza used for different events. On the day of our visit, there was an artisan market with local artists selling their pieces. Our entry was about $12 and I don’t regret one penny. The rooms take you through Puerto Rican history and noteworthy artists from the island. My favorite room was full of African and Afro-Puerto Rican art that catalogued the island’s history with slavery and racism, and included a documentary in which black Puerto Ricans shared their uncensored stories. I was holding back tears. This museum needs to be part of your itinerary!

5 // Eat at Punto de Vista

One of my favorite questions to ask Uber and taxi drivers in a city that’s new to me is, “What are your favorite restaurants?” A gold mine of info about where to eat their local cuisine always follows, and never disappoints. Our taxi driver from the airport (who was a woman, by the way!) and Sara, our tour guide, both said Punto de Vista. After we heard about the same spot from two different people, I knew we were going there. I. Love. This. Restaurant. The staff are so friendly and helpful; we had two amazing waitresses while there, and that’s saying a lot coming from two customers in a food service family! I got veggie mofongo here, and the second time we tried Puerto Rican rice, complete with yellow rice, beans, and sweet plantains. Try to catch them during happy hour, because their 2-for-1 mojitos are to die for. Cue heart-eye emoji. I will be going back to this place for my first meal when I go back to Puerto Rico. Thanks for such an incredible dining experience, guys!

6 // Shop for Souvenirs on Calle Fortaleza

I normally stay far away from touristy souvenir shops, but this trip, I had a really hard time finding the coffee mug. If you’ve been reading my blog a while, you know that I am a coffee mug collector. As of right now, I have mugs from Spain, Italy, Japan, Haiti, New York City, Chicago, Los Angeles, and others that are Disney-themed, or just plain adorable. If it’s worthy of my collection, a coffee mug can’t be just any mug. I have to see it, and know it’s the one. I was getting nervous after a week on the island and not finding the mug. Right after our second meal at Punto de Vista, we headed into a touristy shop across the street at my grandma’s request. Lo and behold, I walked in and there it was! I also ended up getting dresses and a blouse from this place, because they had great prices and plenty of items calling out to me that day. It’s called James Souvenir Shop, on Calle Fortaleza right across the street from Punto de Vista. Its storefront looks like this:

7 // Get Coffee at Cuatro Sombras

My follow-up question to any Uber driver is where I should get coffee. This trip, I didn’t even have to ask. The driver that took us to Casablanca pointed to Cuatro Sombras just down the street and told us we should go there. Your wish is my command, Hector. Especially if delicious Puerto Rican brew is involved! This place is in my top 10 favorite coffee shops in the world. And I’m a millennial from Nashville, where we are snobs about aesthetically-pleasing coffee shops. This place made me one of the best soy milk lattes I’ve ever had, no joke. We went back here twice because we couldn’t resist. If you’re in Old San Juan, type this place into Google Maps and get your caffeine fix with a heavenly, velvety blend.

I’m 100% sure I could spend the rest of my life in Old San Juan. There is a wealth of fun things to do and amazing foods to eat here that I could write a treatise on this area of San Juan alone. I fully believe everyone should go to Puerto Rico and Old San Juan because of the beautiful scenery, kind people, and unmatched experiences. In the rest of my Puerto Rico series, I give tips on budgeting, transport, planning, getting to Vieques, seeing the Bio Bay, where to stay, and much more!

Subscribe for access Puerto Rico packing guide in a small carry-on for 2 weeks!

// Thanks for reading! Let’s connect on FacebookInstagramPinterest, and Twitter. If you would like to know when I’ve written a new post, you can follow me on Bloglovin’ or subscribe to my email list. I also have a newsletter and an Etsy shop for all my fellow design lovers out there. See you next time! 

You may also like...

Leave a Reply