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Old San Juan is the historic district with the cobblestone streets and pretty houses that Puerto Rico is famous for. This part of the city has been vital to the history of Puerto Rico for so long, it is impossible to visit Puerto Rico and not visit Old San Juan. The district has many monuments, restaurants and streets that make it an amazing adventure. Old San Juan is best seen by walking around on foot. This walking guide has the top 12 things to do in Old San Juan with a map to make sure you don’t walk into the ocean.

Looking for things to do in other parts of the city? Checkout my guide to Top 25 Things to do in San Juan, Puerto Rico.

1. Castillo San Felipe del Morro

This is one of two fortresses in Old San Juan that form the history of this place. El Morro was the second fort built on the island for protection from attacks from the sea. It is a formidable 6 level fortress that is ridiculously fun to explore. From the top level you can see El Canuelo, the fort across the Bay of San Juan that was used to create a crossfire and sink enemy ships. El Morro has expansive gardens where you can see kids flying kites on sunny days. This is one of my favorite things to do in Old San Juan.

2. Castillo San Cristobal

This fortress serves as the counterpart to El Morro and was used for land protection against invaders. It spans 27 acres and is created in 3 distinct levels. You can use a brochure to explore the fortress by yourself and it got real spooky when I found an abandoned staircase leading to a small jutting overlooking the crashing waves. This fortress is an amazing example of both architecture and the history of what makes San Juan so special and one thing you should not miss.

3. Santa Maria Magdalena de Pazzi Cemetery

This famous cemetery is know for being the resting place for famous Puerto Ricans such as Pedro Albizu Campos and Jose de Diego. The cemetery is filled with life sized marble sculpture and bright burial sites. Its location across from the Atlantic Ocean symbolize the dead crossing over into the afterlife. You can explore the cemetery in person or glimpse it from atop the walls of El Morro. The tombstones shine bright against the colorful background of the houses on the hills.

4. Puerto Rico Capitol Rotunda

The Capitol Rotunda is a large domed white building at the start of Old San Juan. It is impossible to miss the shining white marble as you pass it by. The dome inside is magnificent with a colorful mosaic that depicts important events in Puerto Rico’s history. The entrance to the building and access to the Puerto Rican constitution is free. You can also call ahead and schedule a tour to get the full effect of this important building in the city.

5. Plaza de Armas

The Plaza de Armas in Old San Juan is a gorgeous shady square flagged by small food stalls and local stores. It has a twinkling fountain in the middle where families and children come out in the evening to play games, socialize and enjoy local food. The plaza is bang in the middle of Old San Juan and you will probably stumble upon it sooner or later. I loved sitting on the bench here and eating the local treats. It is a good way to wind down in the evening before finding a place for dinner.

6. Bar Hopping

San Juan is said to be the birth place of the Pina Colada and it certainly lives up to the legend. The bars in Old San Juan are some of the most amazing establishments I have witnessed. You can find tropical drinks of every kind, from a Lavender cocktail to a freshly made Pina Colada. This is the epitome of what it means to go on holiday in the Caribbean. I loved the bars in Old San Juan and the lazy tropical vibe they all seem to ooze. Checkout my guide to The Top 8 Bars in San Juan, Puerto Rico to see where you should be drinking in the city.

7. Puerto Rican Cuisine

Old San Juan has some of the best Caribbean food I have ever tried. My top 3 restaurants in Old San Juan are Pirilo, Barrachina and Chocobar Cortes. Pirilo has an authentic Puerto Rican cuisine with plates that have a small portion of multiple dishes. They also have a vegetarian plate which was lovely for me. Barrachina is known as having invented the Pina Colada and you can opt to have yours made fresh in front of you. The hotel caters to tourists so it tends to get noisy and crowded at dinnertime. Chocobar Cortes is a gem that has chocolate in every single dish. Your girl loves chocolate so this definitely ranks high on my list.

8. Paseo de la Princesa

Paseo de la Princesa is the street adjacent to the boardwalk that runs across the southern part of Old San Juan on the sheltered bay. During weekends local vendors, artists and musicians set up shop all along the boardwalk and create an unforgettable experience. The vendors have authentic treats like Piragua which is shaved ice mixed with syrups that works wonder to cool off in the heat. This is the place to be during the weekends!

9. Paseo del Morro

This is a hidden gem in the middle of Old San Juan that tourists do not know about. It is an unpaved path right over the water outside the city walls. The trail starts after descending a flight of stairs from inside El Morro and leads all the way to the San Juan Gate at the end of Paseo de la Princesa. It is a scenic quiet stroll surrounded by nature with an unending view of the ocean. You will feel like you are strolling inside a secret garden with the people just a 100 meters up on the wall.

10. San Juan Cathedral

This magnificent cathedral stands in the middle of Old San Juan and is easily accessible at any time. It was built by the Spanish to spread Catholicism amongst the native Taino and African people. It is now the second oldest cathedral in the Americas. The church has an ornately decorated ceiling and beautiful stained glass widows. Visitors are also drawn to the famous graves of St. Pio and Ponce de Leon. The church is an interesting token left behind from another era and worth visiting because of the beautiful art it has.

11. Chapel of Christ

One of the most curious monuments in Old San Juan. It is said that a young rider in 1753 plunged down the cliffs after losing control of his horse at this spot. He miraculously survived and later constructed a chapel here to thank Christ for the miracle. The altar inside the chapel is built with silver and gold. It is flagged by smaller silver ornaments that depict ailments which have been miraculously cured here. The altar is also surrounded by beautiful oil paintings, the most famous of which is El Mirago. The chapel is taken care of by a local sisterhood and has unknown hours.

12. Calle Fortaleza

This street is famous for its hanging umbrellas. The street leads from Plaza Colon to Avenue Ponce de Leon and the part of the street covered with umbrellas is known as Umbrella Street. It is lined with cigar shops, perfumeries, restaurants and craft shops. Even though Old San Juan is filled with Instagramable places, Calle Fortaleza is the cherry on top of that sundae. Checkout this awesome post on how you can spend your entire day just in this one street – A Day in Calle Fortaleza. It is worthwhile to make your way to this famous street and start your adventure into Old San Juan here.