During my recent visit to Puerto Rico, I came up empty when trying to research a great walking route around Old San Juan. The same landmarks were mentioned in everything I read, but there was no mention of how to navigate between them.

Old San Juan really isn’t that big, and we found ourselves wandering around in circles. Based on that experience, I’ve put together what I think is the perfect walking tour of Old San Juan.

If you have all day, this will fill the whole thing nicely. However, you can easily cut one of the forts out or forgo the last part of the itinerary if you have only half a day to spend.

1) Grab breakfast in Old San Juan

I recommend Waffle-Era. Their waffles are to die for, and it’s a great location to start your day. After breakfast, walk a few steps down to the small park at the end of the street for some spectacular views!

San Juan Puerto Rico

2) Walk down to Paseo de Princesa

Turn left on Calle Tetuan and turn right as soon as you can. You’ll see cruise ships and find steps that will take you down to Paseo de la Princesa. There are often little vendors along here selling various knick knacks. Eventually you’ll reach a beautiful fountain and some great views of the water. The path is also a prime spot to view the cruise ships coming in and out.

Fountain in Paseo de Princesa

3) Enter through the Old San Juan Gate

Keep going along the path and you’ll reach the Puerta de San Juan. This is the only remaining of the historic entrances to the city. Once reserved for ambassadors and other people of importance, walk through with your head held high!

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4) Visit Castillo de San Felipe del Morro

Once you’re through the gate, turn left and follow the road all the way to Castillo de San Felipe del Morro. You’ll likely see people flying kites on its huge lawn. It’s $5 to get in, but well worth it. Take your time exploring the old fort, enjoying its spectacular views, and taking advantage of all the great photo-ops!

Visit Castillo de San Felipe del Morro

If you’re up for it, you can also visit the beautiful cemetery, Cementerio Santa María Magdalena de Pazzi, right next the fort.

When you’re finished exploring, make your way up Calle Norzagaray until you reach Plaza del Quinto Centenario (you can’t miss the giant totem pole and sheep statues), and walk up through the plaza.

5) Wander along Calle del Cristo

This is Old San Juan! Take pictures of the beautiful buildings. Browse through the shops. Grab a coffee, beer or snack.

You’ll pass Hotel El Convento, an old convent that is now a hotel. Just past that is Catedral de San Juan Bautista, the second-oldest cathedral in the Americas, and home to Ponce de Leon’s tomb.

Streets of San Juan Puerto Rico

6) View La Fortaleza

Turn right onto Calle Fortaleza to see “The Fortress” where the Governor of Puerto Rico lives. During the holidays, they go all out with decorations, which we enjoyed. Either way, it is a very picturesque street.

La Fortaleza

7) Optional (brief) detour: See the birds at Parque las Palomas

You can continue further along Calle del Cristo if you wish to visit Parque las Palomas, a park with nice views and a ton of pigeons that live in holes in the wall.

Parque de Palomas

8) Grab lunch along Calle Fortaleza

Keep going along Calle Fortaleza (the opposite direction of the Governor’s mansion) to see more of Old San Juan. Be warned, this is a central but touristy street. You’ll see tons of souvenir shops. Feel free to wander and snake your way around Old San Juan.

This is also a good time and area to grab lunch. Many people rave about Chocobar. We enjoyed drinks at a rooftop restaurant called Punto de Vista (in the Hotel Milano). The rooftop has a nice atmosphere, and they have Puerto Rican food as well.

Rooftop views of San Juan

9) Visit Castillo de San Cristóbal

Continue along Calle Fortaleza and you’ll reach Plaza Colón. A little further and you’ll find yourself at Castillo de San Cristóbal, the largest Spanish fort in the Americas.

If you have time, consider taking a tour, as there is a lot of fascinating history here. While I have not had the fortune of taking it myself, I have spoken to Karen at Archtours about her tour of this fort and it sounds incredible. (All of her tours do! She is a professional architect who has worked on many of Puerto Rico’s heritage sites, so she really knows her stuff.)

Castillo

10) Take a breather

After your tour of San Cristóbal, take a little time to relax. This may be a good time to go back to grab a drink, or head back to your hotel to unwind and change.

San Juan cruise ship

11) Enjoy dinner in Condado or a night on the town at La Placita

Feeling up for an evening of fun with the locals? Head to La Placita (especially on a Thursday or Friday). There are plenty of food options, so if you want nourishment but not a late, crazy night, go earlier in the evening or during other days of the week.

If the day has left you exhausted, enjoy a more low-key evening in Condado. There are plenty of places to eat, but we really enjoyed Di Parma Trattoria. It has a great ambience (and great for people-watching) right on Parque La Ventana al Mar (which, as its name implies, is right on the ocean). If oceanfront views are especially important to you, there are plenty of other options.

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