There is something special about exploring Old San Juan on foot. Colorful buildings, cobblestone streets, historic forts, little restaurants, beautiful plazas, and views of the water seem to be around every corner.
We stayed in Old San Juan before our cruise, and I’m so glad we did. Instead of staying near the airport and only seeing the city for a few hours, staying right in the historic district gave us time to wander the streets and enjoy Old San Juan at our own pace.
Staying in Old San Juan Before a Cruise
If you're cruising from San Juan and have the opportunity to arrive a day or two early, I highly recommend staying in Old San Juan rather than near the airport.
Yes, you'll need transportation from the airport when you arrive, but once you're settled into Old San Juan, so much of what you'll want to see is within walking distance.
We were even able to leave our luggage at our hotel while we explored. When it was time to head to the ship, we collected our bags, dropped them off, and still had time to enjoy more of the city before sailing.
We stayed at the Casablanca Hotel in Old San Juan, which I wrote about separately.
Exploring the Streets of Old San Juan
One of my favorite things about Old San Juan was simply walking.
You don't necessarily need a detailed itinerary here. Some of the best moments come from turning down a side street, discovering a colorful building, finding a little courtyard, or stopping somewhere that catches your attention.
Since my daughter's husband is law enforcement, she always has her photo with with other law enforcement when visiting other countries.
Everyone we ran into was super nice!
Castillo San Cristóbal
One place that's hard to miss while exploring Old San Juan is Castillo San Cristóbal.
The massive Spanish fortification was built to help protect San Juan from attacks by land, and its stone walls and sentry boxes are some of the most recognizable sights in the city.
We didn't have enough time to tour the inside during this visit, which is something I would change if I returned.
Even without going inside, the fort is impressive, and the surrounding area provides some beautiful views and photo opportunities.
Don't Rush Through Old San Juan
This is one of those destinations where I think you miss part of the experience if you rush from attraction to attraction.
Look at the balconies. Notice the doors. Wander through the plazas. Stop for something cold to drink. And definitely allow yourself time to take photos.
Old San Juan is incredibly photogenic, but it also has an atmosphere that's difficult to capture in pictures.
A Popular Stop for Something Sweet
During our walk, we came across an incredibly long line for Señor Paleta, known for its frozen pops.
When you see a line that long, you know you've found a popular spot!
Old San Juan has plenty of places like this where it's worth taking a break from sightseeing and trying something along the way.
The Piña Colada and Barrachina
We also stopped by Barrachina, a restaurant that has long claimed to be the birthplace of the piña colada.
According to Barrachina, bartender Ramón Portas Mingot created its version of the famous drink there in 1963.
Whether you're interested in the piña colada story or simply want to see another piece of Old San Juan, the restaurant's courtyard is worth a look.
I especially liked the courtyard. Places like this are part of what makes walking through Old San Juan so much fun—you never quite know what you'll find behind the next doorway.
Parque de las Palomas — Pigeon Park
Another interesting stop is Parque de las Palomas, commonly called Pigeon Park.
The little park has large shade trees and beautiful views toward San Juan Bay, but its most memorable residents are definitely the pigeons.
There are holes built into the old wall where the pigeons gather and nest.
And yes, with that many pigeons comes exactly what you're imagining.
There is pigeon poo everywhere.
If birds aren't your thing, this probably won't be your favorite stop in Old San Juan. But it is certainly memorable!
Give Yourself Time to Wander
Looking back at our visit, I think some of my favorite photographs came from places that weren't necessarily major attractions.
That's one reason I recommend spending at least a little unplanned time in Old San Juan.
You can make a list of the places you don't want to miss, but leave room in your day to simply wander.
Things to Know Before Visiting Old San Juan
Language: Spanish and English are the official languages of Puerto Rico. Spanish is widely spoken, although we found it easy to communicate in English in tourist areas.
Currency: Puerto Rico uses the U.S. dollar.
Getting Around: Old San Juan is very walkable, which is one of the reasons I recommend staying there if you're visiting before a cruise. Wear comfortable shoes—the historic streets and hills can make walking more tiring than you might expect.
Weather: It was hot and humid during our visit in early May. I wish I had carried a bottle of water with me while we explored.
Planning Tip: Before a trip, I like to look at the area on Google Maps and Street View. I locate our hotel and the major attractions we want to visit so the surroundings already look somewhat familiar when we arrive. This has saved us a lot of time trying to figure out entrances and directions once we're there.
