This post gives you a detailed and adjustable itinerary for two days in Old San Juan, Puerto Rico. From sipping Piña Coladas at their birthplace and feasting on classic Puerto Rican dishes to exploring the historic forts and colorful streets!

Now, you might be thinking, how the heck can two days in one place be considered slow travel? If that was your first thought, then you’re in the right place. It means you have yet to experience the colorful historic district of Old San Juan!” 

One could walk from one side of the town to the other in just under 30 minutes. And that’s not a fast-paced 30 minutes either. Technically, you could see all the main attractions here in a couple of hours, but just because you can do something doesn’t mean you should!

What & Where is Old San Juan?

Old San Juan is a historic district located on the westmost portion of Isla San Juan, an island located on the northeast coast of Puerto Rico. The island is accessible by three large bridges that connect to the rest of San Juan, in addition to its modern day ship port. The Spanish built Old San Juan in 1521, making it the second-oldest settlement in the Americas!

La Isla Del Encanto

In Old San Juan, one can easily see why Puerto Rico earns its nickname, “La Isla Del Encanto,” or “the island of enchantment”. Something about the medley of architectural styles, colorful buildings, and narrow streets reminds me of walking through a very humid Venice!

Day One Morning: The Historic Side of Town

Start your morning at Spiga cafe on Calle de San Justo. This place always has the most mouth-watering treats to pair with your morning coffee. They’ve also got delicious homemade pasta for brunch too.

Paseo De La Princesa

From here you’ll then head towards the main port and walk along Paseo De La Princesa. It’s a picture-perfect boardwalk with food vendors, art, culture, history, and a stop at the Raices Fountain overlooking the sea. It culminates at the San Juan Gate, the oldest city entrance in Puerto Rico. To avoid the crowds, consider walking in the morning or during the evening around sunset for the best experience. To go when all the vendors are up, visit on the weekends or holidays.

At the end of the long row of trees that hug the cobblestone path, you will arrive at Raices Fountain. Raices means Roots in Spanish, which is what the fountain represents, the roots of Puerto Rico. 

Paseo de La Princesa ultimately ends at the red San Juan Gate, where the Spaniards would enter San Juan for centuries. They retired it long ago, and now it stands as a historical monument.

Paseo Del Morro

You could enter the gate here and walk up into the town. However, if you’re up for the steps, I highly recommend continuing on the walking path for more amazing views. From the red gate onwards the path becomes Paseo Del Morro (AKA El Morro). It winds around El Morro’s walls and eventually spits you out at the front entrance of the fort.

This path is where all the stray kitties like to hang out, you may even see some kibble and bowls of water that some locals leave out for them. You’ll also come across many large Iguanas, these guys are not as friendly but they make for a cool photo! 

I’m not sure of the total distance of Paseo De La Princesa/Del Morro, but it took me around an hour. Keep in mind, I stopped every five seconds to photograph the cats so it can be done a lot quicker. P.S., check out @saveagato to support the amazing work done by this nonprofit working to rescue these kitties.

El Morro

Immediately upon seeing the vast beauty of El Morro, you’ll understand why it’s such a special place for Puerto Ricans. A brilliant green field unfolds to either side of the long cobblestone path that leads to the forts’ front gate. On sunny days you’ll see people picnicking on the grass and little kids flying kites in the breeze.

The inside of the fort is akin to San Cristobal, though much larger, and with more ocean views. During its nearly 500-year history, El Morro was an important military outpost for Spain and later the U.S. Due to its long, rich history, it was recently named a world heritage sight. The fort boasts views of Old San Juan, La Perla, and the ocean, so you’ll get some beautiful photos here!

*Tip: Keep the receipt for your ticket, it can be used for San Cristobal within two days of purchase*

Lunch in Old San Juan

There are loads of great places to dine in Old San Juan. For your first day here I recommend La Tortuga Bistro. It’s close to El Morro, so if your feet are tired from the morning you won’t have far to go. Many locals I’ve spoken to have named this their ‘go-to spot’ in Old San Juan, specifically for the empanadas. So grab a seat and take some time to relax out of the heat!

Day One Afternoon: The Historic Side of Old San Juan

Cementario Santa Maria Magdalena de Pazzis 

While you’re still up near El Morro, head over to Santa Maria Magdalena de Pazzis cemetery. This cemetery overlooking the ocean dates back to 1863. It’s the burial spot of many famous and important Puerto Ricans throughout history.  I know a cemetery doesn’t sound like the ideal vacation must-see, but this cemetery is not like most. It’s ornately and elegantly designed and boasts beautiful views of the ocean, El Morro, and the small, colorful town of La Perla located on the coastline of Old San Juan.

Promenade to Castille De San Cristobal

From the cemetery, stroll along Calle Norzagaray for a scenic coastal walk leading to Castille De San Cristobal. Use your ticket from El Morro to enter. San Cristobal is smaller than El Morro, but you get a whole different set of views from this side of the isle, specifically from the enclosed lookout on the top floor.

After you explore the Castille, I recommend heading back to your accommodation for an hour or two. At this point in the day, the sun is blaring down and the streets will be at peak crowds from cruise ship tourists. While in Old San Juan, I’d return to my hostel to freshen up, cool off, and do some work.

Dinner in Old San Juan

For your first night in Old San Juan, I recommend grabbing dinner at La Raices (not the fountain!) or Princesa – Cocina Cultura. Depending on when you go, you may need a reservation at the latter, as it can get busy. Both restaurants are renowned for their classic local dishes, such as mofongo!

After dinner, you’re a short walk away from the actual La Raices fountain, where you can go to enjoy some of the best views of the sunset from Old San Juan.

Finally, if you’d like to enjoy some drinks and explore the nightlife, you can head to Moreno’s for $1 beers and shots!

Day Two morning: Art & Architecture in Old San Juan

For your second day in Old San Juan, I recommend using Google Maps to find your general direction and then letting yourself wander the cobblestone streets till you find your new destination. The best way to truly see a place is to get a little lost in it! This way you’ll be sure to uncover all the architecture and colorful buildings Old San Juan has to offer! 

Today, I want you to explore all the streets. I’m only going to give these in a loose order and not by what’s closest to the other, so you can wander around a bit more.

Cafe Botanico

Cafe Botanico is an adorable, plant-filled cafe located in a little yellow building. This was one of my favorite spots to stop for a morning coffee and was where I spent all my time working when it was raining too hard to walk around. The baristas were all so friendly too! I felt like I was sitting in a romance movie. Stop here for a morning or afternoon pick-me-up!

Poets Passage

If you enjoy art, poetry, and music, you must make time to stroll through The Poets Passage. It’s run by Puerto Rican poet Lady Lee Andrews and her French husband and painter Nico Thomassin. Also. if you’re there on a Tuesday, stop in from 7 pm-12 pm for their weekly poetry/music open mic night. I spent a lovely rainy evening listening to a mix of Spanish and English poetry and music!

End of Fort Wall

Back down towards the sea is a little secret garden at the End of Fort Wall. Okay…it’s not actually a secret, and it’s got no walls hiding it, but it feels magical. Amidst a stone pathway and a small stone sculpture, rays of light filter through lush trees rife with blooming flowers. Stand under the trees and look up to watch dozens of butterflies and small birds flit around from tree to tree. You may even spot an iguana while you’re there! I stumbled upon this place by accident, but I spent quite a long time here attempting to capture its magic with my camera.

Banco Popular – Old San Juan Location

The curved facade facing the bay is adorned with bronze eagles, while a towering stained-glass window portrays the shield of San Juan. Framing the glass on either side are reliefs of Greek and Roman gods, serving as a fitting tribute to the architectural influences and ambitions of the district.

Antigua Casino De Puerto Rico

This casino was built in 1910 in the Beaux-Arts style from 19th century Paris. It currently acts as an event space and wedding venue. You may not be able to enter on the day you visit, but the outside is magnificent enough to be worth the trip there. The entire building, including its walls and floors, consists of white marble. Look for the Tiffany-style glass windows, bronze roof, and ornate marble detailing.

Barrachinas

An absolute must-visit in Puerto Rico, Barrachinas is the birthplace of the Piña Colada drink. Get here a few minutes before they open at 11 to ensure a spot, otherwise, you will have to wait in line. I promise the wait will be worth it just for the Piña Coladas alone. Normally, I don’t like Piña Coladas, the rum always tastes too strong for me, but I found them to be quite delicious here! So even if you’re not usually a fan of the drink, I recommend giving it a try…at the least to say you did it!

I didn’t eat lunch here, but the dishes served at the tables around me looked delicious. Overall, most plates seemed to be well-cleaned by the end of people’s meals, always a good sign!

Plaza De Armas

Plaza de Armas, considered the heart of Old San Juan, is a tribute to the main plazas of Spain, and offers unique architectural views on every side of the square. To the northwest, you’ll find Casa Alcaldia, which is a replica of Madrid’s neoclassical city hall. To the west, Antiguo Palacio de La Real Intendencia (Puerto Ricos Department of State office), styled after an Italian high palace. Lastly, to the South you’ll find 20th-century American influences in the building ‘Gonzalez Padin’.

Iglesia De San Jose

Just up the road from Plaza de Armas, you will find Iglesia de San Jose. Originally built in 1532, this is the second oldest standing church in the Americas. This church displays classic 16th-century Spanish Gothic Architecture. Visits inside are welcome.

Cuartel de Ballaja

Cuartel de Ballaja is hard to miss as you walk towards El Morro. The colossal, three-story building was built by the Spanish in the mid-19th century and served as housing for military officers. Now the building houses cafes on the first floor and the Museum of the Americas on the second floor. Tickets are only $6 ($4 for students). The exhibits are relatively small but they are a great opportunity to learn about Puerto Rican history from the point of view of individual artists. This is a particularly great stop on a rainy day.

Anita’s La Mamma del Gelato

At some point in the day, when you find yourself in need of a cool-down, head to Anita’s shop for some extravagant and delicious gelato flavors. They have vegan, gluten-free, and soy-free options as well.

As we come to the end of this two-day journey through Old San Juan, I hope you’re excited to embark on your adventure in this vibrant city. Whether you’re captivated by the historic forts, charmed by the colorful streets, or indulging in the local cuisine, Old San Juan offers something for every traveler.

Not sure when to book your trip to the island of enchantment?

I’ve got you covered! Read ‘when to visit Puerto Rico’ to learn more about when the best time to visit is for different activities, cheaper stays, and smaller crowds! You’ll be booking that flight in no time!

Let me know in the comments which of these activies you’re most looking forward too! And if you’ve already been to Old San Juan, what hidden favorites have you stumbled upon?