Old San Juan Walking Tour with Map for First-Time Visitors

The streets of Old San Juan were practically made to be strolled for hours. With colorful, Spanish colonial architecture, picture-perfect corners, and mesmerizing views of the Carribean Sea, you’re bound to have at least a few awe-inspiring moments during your tour. This post will show you how to put together your own walking tour of Old San Juan. It includes a map so that you can follow along on your phone.

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Time required for this tour

Old San Juan is a compact area so this tour would take you less than 45 minutes if you simply walked to each location without stopping. I would budget three hours to give you enough time to take in the sites, tour the historic buildings, and enjoy the food. 

Items to bring with you

• Comfortable shoes – some of the streets are hilly so it’s a great idea to wear running shoes or something that won’t kill your feet after three hours of walking and climbing fortresses. This is completely up to you. I wore sandals and was mostly fine, except when it came to climbing steep concrete. Next time, I’ll wear some tennis shoes. 
• Water – stay hydrated, my friends!
• Map or GPS – Google maps, Apple maps, whatever works best for you. Puerto Rico is a US territory so your phone service from any major US carrier should work just fine.
• Camera – you can use your phone camera, but a DSLR will capture those picturesque streets so much better! I always recommend the Nikon D3400 for beginners.

Castillo San Cristobal

We’ll start at Castillo San Cristobal, the largest fortress that the Spanish built in the New World. A UNESCO World Heritage Site, this fortress is part of the San Juan National Historic Site, an area that includes fortresses, bastions, and the old city wall. Castillo San Cristobal was built in 1783 to protect the city from attacks when other European powers were trying to take over. 

You need a ticket to tour the inside of the fortress, but there’s an outside area with bastions overlooking the Carribean Sea that anyone can visit. The ticket is $7 and is valid for two days to allow you to see other parts of the San Juan National Historic Site. 

There are three levels to this fortress: the lowest level, the main firing battery, and the observation deck at the top. To get into the fortress, you have to go through some dingy tunnels at the lowest level. Along the way, there are dimly-lit rooms, including a dungeon where prisoners were kept for execution. It was creepy, to say the least. 

Once you get past the tunnels, then everything brightens up – literally. You arrive at the main firing battery with rooms on the periphery that overlook the city. There are plaques explaining what the rooms were used for. Lastly, there’s the top level of the fortress, with breathtaking views overlooking the city. I spent a lot of time here just taking in the scenery.

You can purchase your ticket at the San Juan National Historic Site office. The fortress is open every day of the week from 9 am to 6 pm.

Calle Fortaleza

Calle Fortaleza is a shopping street in Old San Juan, located by the governor’s mansion. There are tons of little shops and restaurants here. This street used to be an Instagram hotspot when there were umbrellas floating at the top. Those umbrellas are no longer there, unfortunately. The street was barricaded during my visit to San Juan because of protests. Not going to complain. People’s livelihoods are more important than my Instagram photos.

La Fortaleza

La Fortaleza, also known as Palacio de Santa Catalina, is the official residence of the governor of Puerto Rico. It also happens to be the oldest, continuously used governor’s mansion in the Western hemisphere. This colorful building sits on a fortification by the Carribean Sea. You can take a free tour of the interior, courtyards, and gardens every weekday from 9 am to 4 pm. Just arrive in person at tour office next to the mansion. I didn’t know that so I’m bummed!  Now you know. 

El Batey Bar

I was looking for some cheap mojitos and found this place on Yelp. When I walked in, I felt like I had stepped into some kind of punk rock tattoo parlor. That’s the vibe of this place. With the somewhat pretentious writings on the wall, like ‘Prohibido Joder,’ I  didn’t have a good feeling about the place at first. 

But it turns out the mojitos were good and cheap. Also, the bartender, Javier,  engaged me in conversation for like an hour. Then, I ended up chatting with some locals at the bar, too. So I ended up liking this bar after all. It’s a great place to unwind and maybe meet new people.  

San Se Marisquería

San Se Marisqueria, located down the street from Outsite San Juan, is the best restaurant in San Juan where I had the privilege of dining. I would recommend their Mofongo, a signature Puerto Rican dish consisting of mashed plantains, and Pulpo, or octopus. Unbelievably delicious! There is also a bar serving cheap piňa coladas. The food, though, is more expensive than at your average Old San Juan restaurant, but I think this place is definitely worth a visit. 

Calle Imperial

Calle Imperial is one of the iconic streets in Old San Juan with a flag of Puerto Rico on the wall. It’s a great place to snap a photo. I wanted to get a photo of myself here and waited for someone to walk by. No one did so I just took a photo of the wall. The struggles of solo travel.

Castillo Felipe del Morro

Further west of Castillo San Cristobal is another fort called Castillo Felipe del Morro, simply known as El Morro. This fortress is also part of the San Juan National Historic Center. It has six levels which were built over the course of 200 years, starting in the 1500s. 

El Morro was one of the original fortifications built by the Spanish to protect San Juan from foreign invaders. Today, it’s popular among locals and tourists alike. The different levels, particularly the higher ones, offer incredible views of the Carribean Sea. All around the structure, you’ll find many garitas, or guard posts, which are a great place to snap a photo. 

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Somto Ugwueze

Hi! I'm Somto. Two years ago, I stopped making excuses, ditched my indecisive friends, and started booking flights. Today, I'm a full-time solo traveler on a mission to inspire young women to seek new adventures.

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