14 Things to do in San Juan | Puerto Rico


                                                  The La Rogativa statue in San Juan

Welcome to the birthplace of humble Pinacoladas - Puerto Rico. Old San Juan is a medieval walled city where legends and true stories go hand in hand. With its narrow cobbled clean street, a la Europe and colorful Spanish Architecture thanks to influences by Spanish conquests, this city leaves everyone wanting more. Surrounded by two massive forts and home to Bacardi Distillery, San Juan is the right amount of fun everyone can have including Jimmy Fallon who enjoyed his visit to the city once!

To celebrate ray of hope and life after the disastrous Hurricane which made tourists anxious if Puerto Rico was indeed ready for them, last year the Governor and his wife implemented a project in La Fortaleza Street in Old San Juan covered in Umbrellas to symbolize that it is indeed now normal to invite tourists in and we welcome all.

                                   The Paseo De Sombrillas at La Fortaleza Street

Don’t be fooled though, this seemingly small city of Old San Juan has all the American necessities you may need including creative small stores, exclusive showrooms of high-end brands & pharmacies and more.

                                              The Poet's Passage at Calle Cruz Old

                                       The Vejigante masks of Puerto Rico made out of Coconut

Traveling within Old San Juan

                                      Take a trolley in Old San Juan or simply walk the alleys.

The best part about Old San Juan is that it is completely walkable. One can take free trolleys which are currently the Golf Carts along some routes, but we admired our walks throughout the city. We did not take the Golf Cart trolley.

Don't forget to visit Puerto Rico Tourism kiosks for information on where to travel and how! We went to Tourist Information Center at Casa Alcaldia / City Hall.

They also give you free easy maps of the city. The Uber rates to and from Old San Juan to Isla Verde or nearby spots in Old San Juan isn’t very expensive either.

The First Thing to do - Take the free tour! 

A free tour is a great way to introduce one to any city’s local culture and history. It gives you a synopsis of a place by an insider who very well know the nit bits of a city. And depending on further where your interests lie, you can expand on it, even though generally these tours are whole in themselves and that’s the beauty of it.

Sara, our tour guide was well acquainted with the historical significance + the cultural knowledge of Old San Juan and I would suggest, if you have one day, savor in the hands of your free guide. You know it, that they would do complete justice to your experience, because they really enjoy telling about their city.

A free tour is a pay-what-you-wish tour. So, if you feel that they have provided the insights that you really needed, its kind to give them a tip!

Old San Juan - The Conquests and The Today in Sight

Our tour guide says, “Today you will see the city casts its magic back to the 16th century. Everything begins when Spain was looking for new ways to arrive to Asia so they could expand their territories. But instead of finding Asia, they found the Caribbean. Christopher Columbus arrived at Puerto Rico in 1493. He originally called the island San Juan Bautista, but thanks to the gold in the river, it was soon known as Puerto Rico, or "rich port;" and the capital city took the name San Juan. We have Plaza De Colon with Christopher Columbus statue in it and that was the starting point of our tour.

                        The Statue of Christopher Columbus at Plaza De Colon

For the first 25 years, Spaniards were establishing themselves in the islands of Caribbean by taking different resources. In 1518, the Spaniards started to expand their territories to Mexico and South and Central America and realized those places were more resourceful. However, Puerto Rico still had significant positioning and those who has control over it would have control over Maritime goods as Puerto Rico is the first island when entering American Hemisphere and was also a gateway for boats into Mexico and Dominican Republic. Hence, the Spaniards started to fortify Puerto Rico.”

Castillo San Cristóbal

The fortification of San Juan was done in different phases and with different attacks serving various purposes. When the British attacked in 1598, the entered from the beach, hid themselves over the high hills and since this area was unprotected took over the city of San Juan. They lasted for 98 days, until plague happened in the city and the British started to die of Mosquitos. Yes! Mosquitos…

So, the Spaniards took over the city again left by British and with funds from Bureaucracy started constructing San Cristóbal Fort that had 3 levels of fence. Their plan was, that they would have different battalions for each level and If any other enemy would try to come, the enemy might take the first line of defense, but the Spaniards would still have 2 other levels to protect it.

The City Wall

Before 1625, the Spaniards believed that they do not need to protect the south because they believed that the only way someone can get in there was by passing the main island that had mountains all the way till the north. So, they protected the north but left the south unprotected. By 1625, without much hindrance, the Dutch soldiers marked all the security system and without been seen and watched entered Puerto Rico. From here, they went to the communities and wanted to go to the main islands and was waiting for the Governor to surrender.

The Governor instead, led the soldiers to eliminate the Dutch soldiers during night. There was a fight. And the Spaniards win. Before the Dutch left, they fired the city and the city got destroyed. Spaniards realized they need to do something to protect it from the south, the funds were collected from the bureaucracy and the wall was constructed.

The Remains of the Wall

Old San Juan city is a yesteryear’s walled city. The walled city was a Military base where the communities were divided by the wall but not enclosed by the wall. Since the entire island was by the wall, most of the entrances were from water. At that time 4 entrances were by water and 1 by land. The land entrance gave access to communities within.

By the 19th century, Spaniards demolished part of those walls to start organizing the city and give access to communities. They also built the first theatre of Puerto Rico in 1932, to organize the communities. The theatre still exists at the Plaza de Colon and is open only when there are performances.

A large portion of the demolished city wall still exists.

Castillo San Felipe del Morro

Between the two forts, Castillo del Morro is smaller, but the view is better. Del Morro means big and to protect. This fort was built to protect from the maritime attack, to protect from the attack by pirates and the city from the native because the natives would be attacking the Spaniards this side over and over again.

Our guide pointed us to Santa María Magdalena de Pazzis Cemetery which like New Orleans had graves over the land surface. In the ends of 18th century and beginning of 19th century, they believed that dead bodies under Churches could bring disease and hence they started making cemeteries outside the city and painted them in lime because they believed that lime helps to kill and eliminate Bacteria. For this same reason, San Juan was completely white long time ago!

14 Things to do in San Juan

  1. Check out these two forts: Castillo San Cristobal & Castillo San Felipe del Morro. The admission fee is $7.00/person. The ticket is good for visiting both El Morro and San Cristobal forts for 24 hours. The fort is open to the public 7 days/week from 9:00am until 6:00pm.
  2. Check out La Fortaleza Street: That’s for selfie-mongers. You’d love taking pictures at this street with umbrellas hanging up there. At the end of the street is the Governors house in light Blue that is the oldest political house in American Hemisphere.
  3. Check out the smallest chapel (Capilla Del San Christo or Chapel of Christ the Savior). So, the story behind the chapel is that Chapel was constructed in the 1750’s as before the Church used to be the only place of celebration. During the day, they would have festivals and one of the festivals by the Spaniards would be horse racing. One of the participants couldn’t stop his horse and fell off the wall. The legend says it that the major of the city started to pray, and both the horse and the man survived and since that was a miracle, a chapel was made. The true story is that they made the chapel to guarantee that the next time the horses would survive as the accident did happen but both of them did not survive.
  4. Next to Capilla Del San Christo is the Pigeon park. Pigeon Park is a great place for adults and kids alike to go and play / feed the pigeons. You can feed the pigeons by buying the pigeon food $1 from the vendor. It’s really an experience of its kind, as pigeons are extremely comfortable with humans and at one time there were many pigeons on me, to flock on the food.
  5. Check out Mofongos at El Punto: My tour guide says, “What a Puerto Rican eat every day is rice and beans with Tostones or plantains and a lot of meat. We do not cook Mofongo at home. People before do not used to eat meat as much only during festivals and here it was mainly pork. Here in Puerto Rico we also eat root vegetables such as Yucca (or Cassava) a lot. It’s originally from Caribbean. She suggested us El Punto to try food and it was awesome. We ordered Cassava Chicken Mofongos with Rice and Beans and it was finger licking good.

  6. Check out Pinacoladas at Baracchina: The Pinacoladas here is out of the world. We did not eat food here, but we sat at the bar and drank Pinacoloda. According to one of the comments on trip advisor, Barachina also keeps your luggage on hold for some time.
  7. Check out Cathedral Metropolitana Basílica de San Juan Bautista: We were standing in front of the Cathedral made by Spaniards in 1521 and was named after San John the Baptist. The Spaniards made the cathedral in a very strange position I.e on top of a hill. Usually they put the Cathedral in the city square. In the 16th century, when the Spaniards would travel all the way from Spain to the Caribbean, the first thing they wanted was to visit the Church and say Thank you to the god that they survived. And that’s why the Church was built over here. The irony of this is though, that they would visit the Cathedral, then the brothel, and then the Cathedral again to wash off their sins.

  8. Check out the artsy Old San Juan. Old San Juan is filled with galleries and creative art by local artists. It is so creative that most shop to me served as an amusement of sorts. They also have their own art and craft market.

  9. Check out La Rogativa statue: La Rogativa is a famous statue in the Plazuela de la Rogativa. According to legends, in 1797 the British intended to conquer the city of San Juan once agin. This time they came in with 68 boats and 8000 troops whereas the Spaniards where only 1500 soldiers. The Spanish were demoralized so the pope prepared the march with all the women of the city at night with torch and crosses in their hand. When the British arrived, they saw the lit torches in the city and thought it’s a huge army. The British retreated and the victory belonged to the church. The true story is that the British did attack in 1797 but instead of attacking on Old San Juan which was already fortified, they chose to enter through Condado which was a slavery territory who resisted the attack. By the time Britishers reached Old San Juan, they were fighting against the slaves, against the communities, the forces hiding behind ambushes and the women who marched with lit torches. At the end they decided to leave, and the victory belongs to everybody.
  10. Try out Limbers: A limber is basically a frozen juice in a cup. In Puerto Rico people love limbers, especially on hot summer days. Try out Coconut, Tamarindo.
  11. Casa Bacardi
  12. We met a couple at El Punto who couldn’t stop but rave about the interesting Bacardi Tour they had the day before. The couple had taken a cruise and Puerto Rico was one of the cruise stops. When we got to know about Casa Bacardi we were excited and immediately booked the tour online. We also got to know that it is the world’s largest premium rum distillery.

    There are two ways to reach there: either you can drive as we did or you can get into a 50 cents ferry from Pier 2 Old San Juan to Cataño pier and then take a taxi to Casa Bacardi which is just 2 miles away.

    As we reached there, we headed to the ticket counter where we were checked in and given a souvenir cup and a token for a complimentary welcome drink. You have got to pick one out of 4 options and I chose Sunrise!

    As our e-token blinked, that was the time we knew our tour was ready and we sat on the trolleys that took us around the complex. The good part is you can carry your cocktail around too. The very first thing that you’d notice is the iconic Bat symbol present everywhere, including the cocktail mats. In 1962, the Bacardi Family has bought a distillery in Cuba. In Cuba the bats were considered lucky. Bats also were symbol of Family Fortune Unity and Health. When Dona Bacardi spotted fruit bats in the distillery, she insisted that the bat sign should appear in every bottle. In the 1960’s a revolution came to Cuba and Bacardi assets were seized.
    Today, 85% of Bacardi rum that is sold worldwide is produced in Puerto Rico followed by Mexico (14%) and India(1%). In 1936, they moved to Puerto Rico and in 1958 they moved to this facility of 127 acres. This facility is big. The trolley passed through distillation columns and distillery and the light blue fermentation tanks that makes 132,000 liters of alcohol daily in the distillation process. We also saw one of the complex buildings designed to resemble a bat in flight. 

    As the trolley stops , we are at the building where we learn about the rum process . It starts with the raw product i.e sugarcane. Much of Sugarcane is imported to this island from Dominican republic or India. Next it is created into molasses, and then finally stored in barrels to create rum. Our guide said that the drink became quite popular with the pirates. The rum that we had around that time was very hard and very crude and that was for pirates who were drinking - it even had put 80% alcohol. 
    From our journey from Sugarcane to Molasses at the recreation room (do not forget to take a selfie with the Bat fountain), they take us through the Rum Aging Barrel Room, The Bacardi Office Recreation and family store where they have preserved Vintage Bacardi Bottles and we get to smell Rum from plenty of mini Barrels. There is also a Bar tasting room where they us about their different types of rum that are made here and lets us sample them. The tour ends at the gift shop. You can also register for the mixology class where you learn how to make different drink. We did not do the mixology class as we had just enrolled for the regular tour.

    Regular tour is for $15 and the mixology class if for $60. You can check the tickets from here

  1. Check out music: Old San Juan has more music than just Regatta. One evening we took a stroll to the end of one street and we get to witness and dance on the real Puerto Rican music.

  2. Bring back souvenirs: My guide suggested the best things to get back from Puerto Rico would be Tobacco & Pittoro Rum. One can also get souvenirs with the native symbols on it such as El Cockee (is a tiny frog that speaks really loud at night , the noise of the animal gives them peace), the symbol of fertility, the sun, water etc.

  3. Smallest Home
  4. Sandwiched between two much larger houses, is the famed yellow door of the world’s smallest house. Also known as the La Casa Estrecha (the Narrow House), it is only 5 feet wide, goes back 36 feet and has 2 stories. People say that the original purpose of this house was slave quarters.


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