One Day in Old San Juan

Spend the day with me in Old San Juan, PR

By Nicole Cody, ACC, CTA
Published February 5, 2025

Yesterday, I found myself solo and with a day to spend in San Juan, Puerto Rico, while my cruise ship was docked in Old San Juan. It was a day filled with music, sunshine, beautiful colors, and a lot of walking! With over 21,000 steps logged while in port, I tried my best to soak up all the sights, sounds and flavors this historic gem has to offer. It was my fourth time visiting San Juan via cruise ship, and each time I'm there, I find myself falling in love with it a little more.

After leaving the ship, I stopped by the pharmacy/convenience store near the port and picked up some snacks and drinks and started walking. Each time I'm in Old San Juan, I find myself getting lost in the colors of Old San Juan. The cobblestone roads, pastel-colored buildings and historic balconies are beautiful. It feels like walking inside a postcard picture. 

After awhile, I found myself at Castillo San Cristóbal. This massive fort, the largest in the Americas, is a World Heritage Site and a U.S. National Park. This National Historic Site was designed to protect the city from land attacks, and it was fascinating to explore. For a $10 entry fee, I was granted access to walk through its tunnels, lookout towers, and sprawling walls at my on pace. I learned that this fortress was built by the Spanish in the 1700s, designed to protect San Juan from attack. The fort is massive, covering almost 27 acres at its peak, and includes a winding tunnel system and displays detailing its history. The sentry boxes (or garitas) standing at the edge of the walls are some of the most iconic symbols of Puerto Rico. Legend has it that one, called La Garita del Diablo, is haunted—though I didn’t stick around long enough to find out. Climbing up the ramparts was more of a workout than I had bargained for but reaching the top and seeing the views more than made up for it. From the top level, I was treated to breathtaking views of the city and surrounding sea. Photos don't do these views justice.

After leaving Castillo San Cristóbal, I started wandering again. I took my time strolling through Calle de la Fortaleza, stopping at little side streets that led to hidden gems like quiet plazas, artisan shops, and charming local cafés. One of my favorite parts of the day was popping into various local stores. From beautifully handmade jewelry to authentic Puerto Rican souvenirs, I couldn’t resist grabbing a few keepsakes to bring home.

No visit to Old San Juan is complete without a piña colada, and although I don't drink, I did stop by Barrachina, the famous birthplace of the drink, just to see it. 

Our ship was scheduled to be in port until nearly 11:00 p.m., so I took my time and explored until my feet were officially exhausted, returning to the ship with a full heart, lots of photos, and dead phone battery.

Old San Juan has a magical mix of history, culture, and charm that makes it impossible not to fall in love with. Whether you’re a history buff, a foodie, or just someone who loves wandering through beautiful streets, this city has something for you. If you’re ever in Puerto Rico—even for just a day—make sure to get out, explore, and soak it all in!