The oldest European-established city in the United States, and third oldest in the Americas behind Santo Domingo and Panamá City, San Juan has been capturing the hearts and souls of visitors since its establishment exactly 500 years ago, in 1521. Charming colorful buildings line streets paved in blue stones. Fountains and churches honor the city’s Spanish heritage, small squares offer peaceful refuges, and two of the most impressive fortresses dominate the landscape. Harbor on one side, bright blue of the ocean on the other, Old San Juan is the small, but densely packed – both literally and with sights for tourists – historic core, and a place not to miss in your lifetime.

But how can one best see Old San Juan to learn about its history? This article will give you my suggestions for how to experience the area in a single day, in two days, or in three, as well as teach you the complex history of San Juan and Puerto Rico in so doing.

Old San Juan in One Day

In a single day, we do the highlights. You’ll start your day at Plaza Colon, a monument to Christopher Columbus (known in Spanish as Cristobal Colon) that sits at the entrance to Old San Juan. Take note of this place. It is the easiest place to order an Uber to leave when you’re done and ready to return to your hotel or Airbnb (or cruise ship). You’ll notice you’re on a hill. Uphill is the mighty San Cristobal fortress, but we won’t be seeing that today. Downhill is the waterfront, and that’s the direction you’ll head.

Old San Juan is no longer a busy harbor. The ships that come in now come to the modern port facilities on the other side, although small cruise ships still dock right here. As you walk west along the water down Paseo de la Princesa, you’ll come to the iconic Fuente Raices, a spectacular fountain. Unveiled in 1992 on the 500th anniversary of Columbus’ sailing, it highlights the island’s Taino (native), African, and Spanish roots. If it isn’t flowing much, just wait a few minutes, as it cycles.

Continuing down the waterfront, you’ll notice the massive city walls to your right. While a settlement here was started in 1508 by Juan Ponce de Leon, San Juan itself was founded in 1521. Puerto Rico was the first large island the Spanish discovered that had both fresh water and a deep water harbor, and this spit of land guards the entrance to that harbor. The city was attacked repeatedly by the English, and in 1625 was sacked by the Dutch, although the fortress protecting the harbor wasn’t taken (more on that in a bit). Following that attack, massive city walls were built and fortifications were added both on the landslide (the aforementioned San Cristobal) and on the other side of the harbor entrance. In fact, Old San Juan has significantly more area dedicated to defenses than to housing, a testament to the importance of the city to the Spanish.

Continue along the walls until you reach the San Juan Gate, a massive opening that was once used as the main gate for visitors to the city, as it led from the water to the cathedral. As you pass through it, you’ll notice just how thick the walls are. This is the only remaining city gate today.

Continue up San Juan Street, which will dead-end into the Cathedral of San Juan Bautista, the patron saint of the city. Entrance is free, although it is closed on Saturdays, and the building is lovely. Built in 1540, it is shockingly airy inside. And for those interested, the tomb of Juan Ponce de Leon is along the left wall as you’re staring at the main altar.

Coming back out of the cathedral, take a right, and another right onto Calle del Sol. A few blocks down you’ll find Deaverdura, a perfect place for an authentic Puerto Rican lunch. (Their tostones, fried plantains, are the best I’ve ever had.)

After lunch, we will head to the fortress of San Felipe del Morro, a huge complex that guards the entrance to the harbor. Begun in the 16th century, the fortress was actively used all the way through World War Two, and you’ll want at least a couple of hours to explore it. (Note, it is built on several levels, and you’ll need to traverse stairs and ramps to see it all.)

Exhibits here in the fortress talk about San Juan from its founding all the way to its being turned over (along with all of Puerto Rico) to the United States following the brief 1898 Spanish-American War, during which the fort was attacked by American warships. Take note of the tracks for cannons, the barracks and kitchens, and especially of the views.

It will now be mid-afternoon, and after walking around in the heat, an iconic island invention, the pina colada, awaits. Back past the cathedral is Barrachina, one of two places on the island claiming to have invented the drink. Have one. Or three. Island life is good.

Old San Juan in Two Days

Have a second day in Old San Juan? Great! Today we will start back near the San Felipe del Morro Fortress at the Museo de las Americas. (It is closed Mondays and Tuesdays, as are most museums in San Juan.) The museum is built into the second floor of what was a 19th century army barracks. Permanent exhibits highlight African art and other things of island historical significance. The rotating exhibits when I was there in January 2022 focused on both modern art and political expression, and some were incredibly powerful.

From here, walk down to the Santa Maria Magdalena de Pazzi cemetery. Built in 1863, it is a bit lacking in upkeep, but is stunningly placed along the water, and is the final resting place for many of Puerto Rico’s early American-age figures of distinction. While the cemetery is visible from the del Morro fortress, it is another experience entirely to walk under the walls and into it.

Again, assuming you aren’t here on a Monday or Tuesday, your next stop is just around the corner from the Museo de las Americas: the San Jose church. Built in 1532, it is the oldest in the United States, and features all of the layers of history: old stone, brick, plaster, and painted stucco. And just outside is a statue of Juan Ponce de Leon. Not notable in and of itself, it made news a couple weeks ago for being toppled by protestors during the visit of King Felipe VI of Spain.

Lunch today will be at Cafeteria Mallorca, home of the mallorca sandwich. Egg, ham, and cheese fill sweet bread and are topped with powdered sugar. Think of it as the Puerto Rican equivalent of the Monte Cristo. It is good.

Finally, we get a chance to explore the Castillo de San Cristobal. One of the largest fortifications ever built by the Spanish, this massive fortress was constructed to guard the city from attack from the land, as San Felipe del Morro protected the water side. What remains today is barely a fraction of what once was, as the fortress originally spanned the entire width of the peninsula, from the ocean all the way to the harbor. As with del Morro, you’ll need to traverse ramps and stairs to visit, but San Cristobal has fewer exhibits and areas open to visitors, making it a shorter experience. The views, however, are unparalleled.

Old San Juan in Three Days

If you are lucky enough to have a third day in Old San Juan, your options of how to spend it abound.

If you like history, consider the Museo de San Juan or Casa Blanca, the home built for Juan Ponce de Leon. (He died before moving in.) If you want more pretty scenery, you can walk from the Fuente Raices all the way along the walls to the tip of del Morro along the Paseo del Morro. (There is little shade, but it is a perfect view of the iconic garitas, or watch towers, that have become one of the symbols of Puerto Rico.

If you want to shop, Calle de Fortaleza and Calle San Francisco have a ton of souvenir places. Prefer to sip a cold drink? Consider the historic La Casita, a pink hut along the harbor serving the Sexy Colada, one of the best pina coladas I have tasted.

Old San Juan is a world-class destination, and it truly has something for everyone. Whether you have a single day, two days, or even three days to explore, it will capture your heart, mind, and stomach. Enjoy!

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