48 Hours in Old San Juan: A Travel Guide

48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of a woman standing on a cobblestone street surrounded by colorful buildings in Old San Juan, Puerto Rico.

If you’re thinking about your next Caribbean getaway, Puerto Rico should be on your radar. For starters, if you’re a U.S. citizen, you don’t need a passport, and you won’t need to worry about exchanging money – which is super convenient. There’s also so much to do in Puerto Rico. You can head to the beach, explore the city, visit the only rain forest included in the US National Forest Service, hop on a cruise and more. No matter what type of traveler you are, Puerto Rico has something for everyone.  Which is why I’m so excited to share my Old San Juan travel guide with you!

Most importantly: Puerto Rico is still recovering from Hurricane Maria, and one of the best ways to support the island is to book your next trip there. Your tourism dollars can make a world of difference! The touristy spots on the island are back up and running and are perfectly fine to visit.
 

48 Hour Old San Juan Travel Guide

We decided to explore the colorful Old San Juan for a few days after our experience with Celebrity Cruises back in the spring; and it is one of the most charming places I’ve ever visited. There might not be any beaches in Old San Juan, but the colonial architecture, the history, and the incredible food scene will pull you in.

If you’re visiting Puerto Rico, you could visit everything you wanted to in Old San Juan in 1-2 days. After that, I would venture out to either the beach or the rain forest. Here’s what you should do if you have 48 hours to spend in Old San Juan!

48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of colorful houses in Old San Juan, Puerto Rico.

48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of the Old San Juan Bay
48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of a woman standing in front of Casa Bacardí Puerto Rico

48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of a woman walking down Colorful Streets in Old San Juan

Getting There & How to Get Around

Almost every major U.S. airline flies into Luis Muñoz Marín International Airport (SJU), and there are daily, non-stop flights from DCA to San Juan. Old San Juan is only a 20-minute drive from the airport, so it’s super convenient to get into town.

Old San Juan is pretty small – you can walk the entire neighborhood. The streets are pretty narrow and get congested pretty quickly, so if you need to rent a car during your trip, I wouldn’t recommend keeping the car overnight in Old San Juan. Uber is also available if you want to get out of the city.

History and Sightseeing in Old San Juan

48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of a woman visiting Forts in Old San Juan

The Forts

Old San Juan is home to six forts that are 475+ years old – and are quite the sight to see! The biggest and most popular fort on the island is Fort San Felipe del Morro. It’s a six-level fort that overlooks the San Juan harbor and is one of the most stunning sights on the island. You can either do a self-guided tour or join in on a group tour on weekdays.

48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of a woman visiting Casa Bacardí Puerto Rico

48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of a woman mixing a Bacardi drink at Casa Bacardí

Take a Day Trip to Casa Bacardí

You can take a quick ferry across the bay to Casa Bacardí, AKA the headquarters of Bacardi Rum. We did a tour of the facility, and took a mixology class, and learned how to make three cocktails with Bacardi rum. We loved every minute of the experience!

48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of a woman walking under Colorful Umbrellas on Fortaleza Street - Old San Juan Puerto Rico

See the Colorful Umbrellas on Fortaleza Street

Do it for the ‘gram: there’s a gorgeous Umbrella installation on Fortaleza Street that’s a must-see. They change the color of the umbrellas regularly – when I visited in March, the umbrellas were pink for Women’s History Month, but usually, these umbrellas are multi-colored. If you’re wondering how I got a photo with no one in it…I woke up at the crack of dawn to get the shot! 🙂

48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of a woman at Paseo la Princesa Old San Juan

48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of Paseo la Princesa Puerto Rico

Take a Stroll Along Paseo la Princesa

This was probably one of our favorite walks in the city. Paseo la Princesa is located right near the cruise ship docks and is the most beloved promenade in Puerto Rico – and it dates back to 1853. You can enjoy incredible views of the bay, great food, and enjoy live music here on the weekends.

48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of tacos from La Madre Old San Juan

48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of a Señor Paleta
48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of Bartender at La Casita de Rones

48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of Cocktails at La Casita de Rones

Where to Eat & Grab Drinks
  • Waffle-era Tea Room: If you’re a fan of waffles, this spot has a great selection of both sweet and savory dishes.
     
  • Spiga: Cute little breakfast spot that serves fantastic coffee and homemade bread, and delicious baked goods.
     
  • El Jibarito: Looking for authentic Puerto Rican cuisine? This is your best bet. It looks like a hole in the wall, but the dishes are amazing!
     
  • La Madre: Great tacos, margaritas, and a cute little patio that’s great for people watching.
     
  • Señor Paleta: Need a sweet treat? Señor Paleta is known for their ice cream pops, and they have multiple locations on the island.
  • Barrachina Restaurant Old San Juan: Home of the original Pina Colada.
     
  • La Casita de Rones: Located along the Paseo la Princesa, this pink house is the most charming spot in town to grab drinks with friends.

48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of a woman looking down Umbrella Street in Old San Juan

48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of Old San Juan coastline.
48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of Most Narrow House in Old San Juan

48 Hours in Old San Juan: A Travel Guide by popular Washington D.C. travel blogger, Alicia Tenise: image of Bloggers Alicia Tenise and Kerrie M Burke in Old San Juan Puerto Rico

P.S. — Check out my friend Kerrie’s guide here!

Have you ever been to Old San Juan? Let me know in the comments!

Photos by Tom McGovern