How to Explore Old San Juan (From a Local)

There are a thousand ways to explore Old San Juan, but there's a way to do it right: pacing your energy, knowing where to stop, and using the tricks only locals tell you. Let me walk you through my route.

Where to start (and how not to wear yourself out)

The first thing is deciding where you begin, and this choice saves you energy.

You can start from Plaza Colón, which connects easily to everything, but be ready to walk uphill. Or you can start from El Morro and work your way down, which is how I recommend it if you want to save energy. Going downhill is always kinder than climbing under the Caribbean sun.

The two forts (and the ticket trick)

Here's what almost nobody tells you: when you enter Castillo San Felipe del Morro, don't toss your ticket. That same ticket also gets you into Castillo San Cristóbal, and if you don't see both on the same day, the ticket usually stays valid the next day. (Check the exact validity when you enter, since conditions can change.)

And a tip: most people only talk about El Morro, but San Cristóbal is spectacularly beautiful, with a network of tunnels that's absolutely worth it. Don't skip it.

Between the two forts it's about a mile if you go along the road that hugs the coast, with an ocean view that is, on its own, part of the experience.

Past El Morro: Ballajá and its treasures

Once you cross El Morro you reach the Cuartel de Ballajá, and here's a practical detail you'll be grateful for: it's one of the few places in Old San Juan with public restrooms. In the rest of the city, restrooms are usually inside restaurants and cafés (and you typically need to buy something to use them), so take note.

Ballajá is also home to Café Don Ruiz, a boutique spot with spectacular Puerto Rican coffee, beautiful, almost museum-like. Here you can try a mallorca sandwich, that sweet bread so traditional to us, delicious any time but especially for breakfast.

Nearby you've got the Museo de las Américas (admission has a cost) and the Museo de San Juan (this one is free). And next to the Museo de San Juan is the Callejón de la Bandera (Flag Alley), a corner where many people love to take photos for Instagram.

The San José Church and Calle San Sebastián

Continuing from Ballajá you reach the Iglesia San José, next to the Plaza del Quinto Centenario. It's not always open, but if you find it open, go in: it's a spectacular stop for its relics and its medieval design.

And if you're into a festive atmosphere and local liquors, you can't miss Calle San Sebastián. It's the festive street of Old San Juan, and where our carnival was born: the Fiestas de la Calle San Sebastián (the "SanSe"), which at the end of January draw half a million people in a single weekend and shut down San Juan for the event. If you're in that mood, order a chichaíto, a shot of anise liquor that sometimes comes in different flavors, very typical here.

Calle del Cristo: the historic heart

From San Sebastián, use the Nono's bar as a reference point, because the street that goes down from there is Calle del Cristo, home to most of Old San Juan's historic landmarks: the Cathedral, the Convent, the Parque de las Palomas (Pigeon Park), La Fortaleza, the Capilla del Cristo, and Anita's Gelato, that famous gelato that hits perfectly after a hot day.

If you're traveling with kids, the Parque de las Palomas and flying chiringas (that's what we call kites) at El Morro are must-dos; that's how we Puerto Rican kids grew up. If you don't have a chiringa, don't worry: across from the Plaza del Quinto Centenario, facing the coast, there's a little white kiosk where they sell them.

Two treats you can't miss

As you walk, look for a piragua: shaved ice with syrup, in flavors like tamarind, raspberry, or passion fruit, so typical of ours. You'll find it at the wooden carts in front of El Morro or the Museo de San Juan, where someone shaves the ice block right in front of you. It's the most refreshing drink for the heat while you enjoy the cobblestone streets.

And speaking of the cobblestones: go to Old San Juan in comfortable shoes, preferably sneakers. San Juan still has its original cobblestones, beautiful but uneven, so you'll want to walk carefully.

Shopping and my favorite circuit

Calle del Cristo connects you to Calle Fortaleza. If you're after shopping, Fortaleza is the place: shop after shop, with all the charm of the colonial city (though you'll find stores all over San Juan).

Here's how I do it: I walk down Calle del Cristo and exit through the little side street next to the Capilla del Cristo. From there I head to the Paseo de la Princesa, full of artisans, and when I reach the fountain, I go right to walk along the city wall and take in the coast, with a lovely view of the ocean. At the end, on the right, is the Puerta de San Juan (San Juan Gate), a hugely important historic spot: it was one of the gates into the walled city in the old days. If you keep straight from there, you loop back to Calle del Cristo in front of the Cathedral, like a circuit. And after that, I move over to Calle Fortaleza, turning left.

Why do I do it this way? Because Calle Fortaleza takes you back to Plaza Colón, where it's easier to catch a ride.

A tip about transportation within Old San Juan

Although rideshare apps do reach the middle of Old San Juan, I don't recommend it from inside. The traffic, the narrow one-way streets, and the cobblestones reduce driver availability, which drives the price up and makes the wait too long. It's much better to walk to Plaza Colón and catch your ride from there.

Beyond the historic core: the port and where to eat

From Plaza Colón you don't have to leave right away. You can head to the port area and its restaurants. If you want something simple and quick, there are food trucks. But if you're in the mood for a good restaurant, an important tip: don't wait until you're too hungry, because getting a table in Old San Juan can take more than an hour.

Some restaurants I like: Raíces for traditional food, and Cayo Caribe for seafood (they also have meat options and a vegetarian menu). And if you follow a vegetarian diet, another recommendation is the Stuffed Avocado Shop, on Calle San Francisco.

It's worth starting Old San Juan early if you're going into the forts, because it can take all day. But I always recommend seeing it by day and by night: the energy is completely different, and each has its own charm.

A crossing few people make: the ferry to Cataño

If you're feeling a bit more adventurous, take the ferry to Cataño. It's not expensive, the bay crossing takes about twenty minutes, and it runs frequently throughout the day. On the other side, a spectacular view of Old San Juan awaits, like Hoboken looking at Manhattan, but with a Caribbean feel.

In Cataño there are two restaurants I love: Casilda and Don Tello (and plenty of others that are also great). And there's an open-air playground right by the ocean, which makes it ideal for parents and kids alike.

Explore it at your own pace, without worrying about the rest

Old San Juan is meant to be walked, that's part of its magic. But getting there, moving between areas, or combining it with other parts of the island in a single day, is where private transportation makes your life easier.

That's what Route to Explore offers: private transportation at your own pace, to the stops you choose. You walk and enjoy the old city; I make sure you get there and connect the rest of your day stress-free.

If you'd like to explore San Juan and beyond with that peace of mind, request your private ride here. It would be my pleasure to be part of your journey.