Self Guided Walking Tour of Old San Juan – Part 1

La Casita

So you decided to spend some time exploring Old San Juan? You will not be disappointed! The old city is a small area, only 7 square blocks. But there is so much to do and see in that small area that you can spend days there and never see everything. Or if you are in a hurry, you can get an feel for the city in just a few short hours.

Thanks to conservation efforts, this beautiful old city remains largely as it did 300 to 400 years ago (but better, due to many modern conveniences!) with about 400 restored 16th- and 17th-century Spanish colonial buildings.

I will break this tour up into a number of parts. Part one will be your guide from the Casita to El Morro along the Paseo de la Princesa, and up Calle Cristo.

One of the first things you will probably notice about the old city is the streets. The streets here are blue cobblestones ( or many of them were until they started making OSJ a walkable town- now many have been replaced with modern blue/grey pavers).

Our first stop will be at the Puerto Rico Tourism Company Information Center. It is on the far west corner of La Marina street (across from Pier 1 and the Casita -the little yellow rose building). Here you will find air conditioning and a bi-lingual staff to help you plan your day. They can give you ideas and information about what is happening, the hours of operation and other important suggestions, like where to eat.

The Visitor’s Center (phone 787-722-1709) is located across from the Plaza de la Darsena and is open everyday from 9:00am until 5:30pm.

After you have your information and maps, head outside and enjoy the Bahia de San Juan (San Juan Bay). From here, you can see the cruise ships in port. The number of ships vary depending on the season, but it there is usually at least one ship in port at least 4 days a week (always on Saturdays and Sundays).

When you are ready to start your tour, start walking west (to your left if your back is to the bay). In this plaza, you will find nice benches with a view of the bay and little rose colored Casita (which is a RUM BAR!). Also here you will find an outdoor crafts market is usually open all day on weekends and on some week days depending on the cruise ship itineraries.

Continue left down the Paseo de la Princesa. This lovely street is tree lined and has lovely gardens, benches, statuary, and a nice shady restaurant. You will usually find some vendors, and there is a clean public bathroom (50Β’) on the left side.

Puerto Rico Tourism Company

You can’t help but notice the massive City Wall to the right. The city wall or La Muralla was built around the city. Started in the early 1500’s, it is almost 20 feet thick in places and up to 60 feet tall in places. It was constantly being extended as the city grew and was finally completed in 1782. It was built to protect the city against enemy attacks. There is a nice shady garden, some statuary, and a children park for everyone to enjoy.

As you continue along the Paseo, you will come to La Princesa. This lovely building was once the San Juan jail. (Notice that the criminals were kept outside the city walls!). Now restored, it houses the Puerto Rico Tourism Company (phone 787-721-2400). Take a little time and go inside. The building is air conditioned and always has a changing collection of art. Ask for a quick explanation of the jail portion, then go out to the back courtyard and go to the right, through the tiny walk between the buildings to see the jail cells. It is open weekdays.


As you continue down the Paseo, you will see a beautiful fountain with a bronze sculpture by Luis Sanguino called “Raices“, which symbolizes the island’s cultural roots.

At the end of the promenade, you can see across the bay to Catano. The big golden cream colored building you see (with the distillation “chimneys” and wind turbines) is the Bacardi Rum Factory building. You can take a tour of the Bacardi operation. You can either drive yourself, or take the public transport (bus or La Lancha ferry- whichever is running, from Pier 2 in Old San Juan to Catano and then an Uber or Taxi to the rum factory.

Continue on the Paseo to your right. You will see a metal sculpture that looks like “spikes” on the right. Later on the right is a sculpture of Queen Isabella in a nice little cool sitting area.

San Juan Gate

Continue along the Paseo. Here you will find the City Gate. You have a choice to either continue on the walk outside of the city wall, or go through the gate into the city.

If you choose the walk along the wall, the trail is called the Paseo del Morro. It is 3/4 mile long one way. This walk follows along the city wall to below El Morro fort. The trail actually ends at El Morro fort. You can go to the end, follow path up to top and enter El Morro Fort area from there. They have steps that will connect the grounds outside the fort to the Paseo. Along the route, you will be able to get many great photos of El Morro, and the Garitas (guard towers). It will be hot, and there are no trees for shade. You can not walk off the trail, it is monitored by guards. You will see many cats on this path. They are protected by the Parks Department – do not touch or feed them. They are spayed/neutered, vaccinated and fed by a local animal organization called Save a Gato . This paseo is open 6:00am-10:00pm daily, but the Fort area entrance is only open 9am – 6pm daily (before or after that you need to walk back along the Paseo to the gate). Bring a hat, water and sun screen!

But our tour will take you through the City Gate. This is the only remaining city gate. It was one of six original massive wooden doors that, centuries ago, were closed at sundown to protect the residents. This pretty red-painted Puerta de San Juan or San Juan Gate is where you re-enter the city. Above the gate is inscribed “Benedictus qui venit in nomine domini”- Latin for “blessed is he who comes in the name of the Lord”. As you walk through, notice how the wall is about 15 feet thick. Go straight through the gate and up the hill. You are following the same path many sailors took after a long voyage – straight up the street, to the cathedral, to thank God for a safe journey.

As you are walking up this street, try to peek into any buildings being renovated. These are 400 year old houses that have beautiful Moorish tile work, and lovely open inner courtyards.

San Juan Cathedral

Just before you get to the Cathedral, you will pass a small shady park. Here you can sit, relax and people-watch in the cool shade.

The San Juan Cathedral is a 450 year old church. Ponce De Leon is interred here. The building is constantly being restored and it is very pretty – go in and take a look. They ask a donation ($2). Mass is still held here. Open daily.

Once outside the Cathedral (with your back to the cathedral) turn right and continue going up the hill on Cristo Street. Be sure to make stops along the way. There are many restaurants, bars, art galleries and museums – so take your time and explore!

At the top of the hill you will find San Jose Plaza. Here you will find the San Jose Church, which as of 3/21 has finished being restored! The Church is open Tues- Sat 9am – 4pm. It is the oldest church in San Juan and has some wonderful features and art..

In the corner by the church door, you will find the back entrance to the old Dominican Convent. It housed the National Gallery – about 150 artwork pieces from Puerto Rican artists from the last few centuries. This museum is currently closed, but when it reopens, Stop in. It’s definitely time well spent.

El Morro Fort

Cristo street ends here, so turn left – you will be at the Plaza del Quinto Centenario. This park has a sculpture of a Totem pole and, down the steps, you will see a fountain that the kids love to play in. From here you will see El Morro across the field.

We’ll pick up the tour at El Morro in part 2 of this “self guided walking tour” series of articles.

You can spend many days taking in all that Old San Juan has to offer. Plan on at least one full day. assumes no responsibility regarding your safety when participating in the activities described in this article. Please use common sense! If your mother or that little voice in your head tells you that you are about to do something stupid … then don't do it! Read more about Safety →

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