27 Things to do in Old San Juan, Puerto Rico

categories: USA Travel

Things to do in Old San Juan, Puerto Rico

Old San Juan, Puerto Rico, is the 3rd oldest city in the Americas. Only Santo Domingo and Panama City are older. It is a city that is cherished by Puerto Ricans and by visitors alike. This beautiful, vibrant city is a treasure and one of the most beautiful cities in the United States. Learn what to do if you have a chance to explore this city.

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El Morro - Old San Juan, Puerto Rico

Tour El Morro

If you only see one thing in Old San Juan, it should be the El Morro fortress in the northwest corner of the island that holds Old San Juan. The Castillo San Felipe del Morro was built by the Spanish to protect the entrance to the harbor. The oldest portions of the fort were built starting in 1539 but upgraded over two centuries.

The fort was taken only once, by the English, in 1598. They attacked the fort from the land and captured it, but they were forced to flee because of an outbreak of dysentery. The Dutch had less success in 1625 when they attacked during the Eighty Years’ War (or the Dutch Revolt). A marker, halfway up the hill before El Morro, marks how far they advanced before they gave up, set fire to Old San Juan, and sailed away.

El Morro is now part of the San Juan National Historic Site and is managed by the U.S. National Park Service. Admission is $10 for a 24-hour pass that will also work at Castillo San Cristóbal and Fort San Juan de la Cruz across the entrance of the bay.

El Morro - Old San Juan, Puerto Rico

El Morro is still surrounded by a dry moat and its protective walls. The guard towers along the walls ate iconic in Puerto Rico and are featured on the local license plates.

Cementerio Santa María Magdalena de Pazzi

Cementerio Santa María Magdalena de Pazzi

On the north side of the old city walls by El Morro is one of the most prestigious places to be buried in Puerto Rico. The Santa María Magdalena de Pazzis Cemetery is the final resting place for many famous Puerto Ricans. Even if you have not heard of any of its residents, the cemetery has an interesting collection of tombs and monuments.

Cementerio Santa María Magdalena de Pazzi

The location is stunning as it is sandwiched between the waves of the Atlantic Ocean and the old city defenses. The cemetery was started by the Spanish in 1863, late in the Spanish period.

The cemetery was originally cared for by a group of Carmelite nuns housed in what is now the Hotel Convento.

Old San Juan walking tour

Take a Walking Tour

One of the best ways to start a visit to any city is with a walking tour, and Old San Juan is no exception. I arranged a tour using Patria Tours, which I booked through Get Your Guide. The tour, San Juan: El Morro Fort and Old Town Walking Tour, starts in front of the cruise ship ports and proceeds up the hill into the older parts of Old San Juan, like the Cathedral, and ends at El Morro. You better bet that some of the things I learned about the history of Old San Juan came from my wonderful guide Jorge. 

You need to wear sun protection and good walking shoes and bring a water bottle because Old San Juan is not flat and can get quite warm. 

Catedral de San Juan Bautista

The Cathedral in Old San Juan is the second oldest church in the Americas and the oldest church in the United States. The oldest part of the church can be found in a chapel behind and to the left of the current altar and dates to 1540. The original church, built in 1521, was destroyed by a hurricane.

The entire island that we now know as Puerto Rico was Named San Juan Bautista (Saint John the Baptist) by Columbus, and around the time this church was started, the city was known as Puerto Rico or “rich port.” For some reason, early during the Spanish period, the city and the island switched names. 

There is a memorial in the oldest part of the church about the first event where the people of the island identified themselves as Puerto Rican. So this building is an important part of the Puerto Rican identity.

Old San Juan Cathedral

Notice the dome of the cathedral with its money-saving architectural details painted on instead of constructed. 

Catedral de San Juan Bautista

Inside the cathedral, you can find the tomb of Spanish explorer Ponce de León who was the first governor of the island. There is no evidence from the time that Ponce de León ever searched for the fountain of youth, but he did travel to Florida in 1521 to try and colonize the area for Spain. He was wounded by the local natives in a skirmish, the colony was abandoned, and he died from his injuries. 

You can also find the tomb of the only Roman Catholic cardinal from Puerto Rico, Luis Aponte Martínez, and a shrine to Carlos Manuel Rodríguez Santiago who is the only Puerto Rican to be beatified.

The street directly in front of the city is Caleta de San Juan which runs a short two blocks down to the last remaining gate on the city walls, Puerta de San Juan. Stopping at a city’s cathedral to thank God for a safe voyage was a common practice in an age when crew mortality on a long voyage could easily be 20%. 

 

St Pio, San Juan Cathedral, Puerto Rico

See The Body of a Saint

While Puerto Rico may not yet have a saint of its own, you can see the wax-covered body of Saint Pius in a glass coffin in the cathedral. Saint Pius (St Pio) was an early Christian martyr, a Roman soldier who was killed for his faith. In 1815, the bishop of San Juan, Mariano Rodríguez de Olmedo, wanted a relic for his cathedral, and the Pope gave him the body of St. Pius. The bishop took the body to Spain to have it prepared for display, but for some unknown reason, it was left in Spain until then bishop Pablo Benigno Carrión visited Spain in 1962 and was told he had a saint’s body… apparently in lost luggage.

Old Town Square - Old San Juan, Puerto Rico

Visit The Old Town Square

The tiny park opposite the Cathedral of Old San Juan is the original main square of the city. It is a small square, but you can often find a street musician or a local ice cream vendor at the park. One side of the park is Calenta de San Juan running down to the old town gate. The other side is the Caleta de las Monjas (the way of the nuns).

Hotel Convento

Stay in a Convent

The large imposing building on Caleta de las Monjas opposite the San Juan Cathedral and the old town square is Hotel Convento which is, as the name would suggest, an old convent. Construction started on the convent in 1646. The Monasterio del Señor San José de la Orden de Nuestra Señora del Carmen (Monastery of Saint Joseph of the Order of Our Lady of Mount Carmel) opened in 1851. It was the home of a group of Carmelite nuns. 

In 1903, the convent was closed. The massive building was just too expensive to maintain. In 1959, the heir to the Woolworth fortune, Robert Woolworth, purchased the derelict convent and turned it into a grand hotel. This was part of a large effort to modernize the economy of Puerto Rico called Operation Bootstrap. It should be noted that the rooftop pool overlooking the cathedral was not part of the original convent.

Hotel Convento has two different restaurants, including one in the interior plaza. Even if you don’t stay here, take a quick peek at the interior of the building.

[site22]old san juan[/site22]

Casa Blanca

Visit the Other White House

The oldest house in Old San Juan is Casa Blanca, or “White House.” It was built for the original governor of the Island, Ponce de Leon. The governor/explorer died on his Florida expedition before he was able to live in the house, but his family occupied the house until the middle of the 1700s. The house is now a history museum which is open Tuesdays to Sundays in the morning and in the afternoon, with a break for lunch.

the Piña Colada

Try a Piña Colada

Officially the Piña Colada was invented as a cocktail by bartender Ramón “Monchito” Marrero at the Caribe Hilton in Old San Juan in 1954. But, if you tried one of his Piña Coladas you wouldn’t recognize it. Sure, it had rum, coconut cream, and pineapple juice, but it was served over the rocks. The blended drink that you know and love was invented at the local restaurant Barrachina which still serves the wonderful blended drink. 

La Factoria

Party on Calle San Sebastián

The most lively street in Old San Juan is Calle San Sebastián in the northern part of the city, not that far from El Morro. Here you can find bars like La Factoria, which was named one of the 50 best bars in the world.

In the 3rd week of January, there is a Christmas festival on Calle San Sebastián. The festival celebrates (among other things) the early Christian martyr San Sebastián, so expect to see a few images or statues of a man pierced with arrows. Also, expect to see a few cabezudos or full-head puppets.

La Fortaleza

Visit La Fortaleza

The official name of La Fortaleza is El Palacio de Santa Catalina (the palace of Saint Catherine). It was built as part of the city’s defenses but, since the mid-1800s, has been the governor’s mansion. You can get a 30-minute guided tour of the gardens of La Fortaleza Monday through Friday between 8:15 am and 3:30 pm. A tour must be booked in advance. Depending on what is happening on the day of your visit, you may also get a peek inside the building. The building has housed at least 170 governors of Puerto Rico and is the oldest executive mansion that is still in use in the Americas.

La Fortaleza, the city walls, the fortresses of El Morro, Castillo San Cristóbal, and San Juan de la Cruz comprise the UNESCO site La Fortaleza and San Juan National Historic Site in Puerto Rico.

Plazuela de la Rogativa

Learn the Legend of La Rogativa

At the Plazuela de la Rogativa, you can see an interesting statue of a bishop and 3 women bearing torches. This statue commemorates yet another attack on the city and the legend that surrounds it.

The English again tried to take the city of Old San Juan in 1797 as part of the Anglo-Spanish War (after the French Revolution and only 2 years before Napolean became emperor). The governor of San Juan encouraged a “rogavita” which is a religious procession that comes from the Spanish word to plea. A procession of the bishop and torch-bearing women marched through the streets at night. They started at the Cathedral, and with hymns, bells, and prayers, they pleaded with God to deliver the city. 

The legend goes that their prayers were heard because the British commanders, Admiral Sir Henry Harvey and Lieutenant-General Sir Ralph Abercromby, seeing the procession, thought that it was the arrival of reinforcements and took their 68 ships and 7000 troops and sailed away. Of course… some point out that the stubborn defense by 4000 militia, 200 Spanish soldiers and a ragtag group of 300 French privateers, 2000 armed peasantry, and paroled prisoners might have also influenced that decision, but never let facts get in the way of a good legend.

Plazuela de la Rogativa is situated on a mirador along the old city walls. From there, you can get a good view of La Fortessa and of the only remaining gate of the city, Puerta de San Juan.

Old San Juan, Puerto Rico

Old San Juan, Puerto Rico

Explore the Cobblestone Streets

Old San Juan is known for its Spanish revival architecture and its colorful buildings. The architecture dates back centuries, but the colorful buildings only go back to the 1950s when a serious effort was put into developing Puerto Rico as a tourism destination. Students of history will note that the development of Puerto Rico happens around the same time as the Communist Revolution in nearby Cuba. Before the rise of Castro, much of the U.S. Tourism in the Caribbean was heading to Havana instead of Old San Juan. 

Many, but not all, of the streets in Old San Juan have cobblestones. The oldest of these were brought over to the island as ballast in ships. These same ships were then loaded with gold and other treasures of the new world to return to Spain. 

Plaza de Armas

Sip a Coffee in Plaza de Armas

Plaza de Armas is behind the San Juan Cathedral and the Puerto Rico Department of State building and in front of the SuperMax, which is the only grocery store in Old San Juan. It is known for its beautiful fountain with 4 statues that represent the 4 seasons. 

Plaza de Armas Old San Juan

There are two kiosks in the park where you can get a coffee and a pastry, one of which has some shaded tables to take a break. There are also public restrooms in the park. If those are not open, Marshalls department store next to the park has public restrooms.

statue of Puerto Rican composer Tite Curet Alonso

If you look closely, however, you will see a 5th statue which is a man sitting on a park bench. This is a statue of Puerto Rican composer Tite Curet Alonso (1926 – 2003). Alonso composed 2000 different salsa songs, starting at the age of 15. At least 200 of those songs could be considered hit songs. Alonso moved to New York City in 1960 and lived for the rest of his life on the mainland. When he died, his body was returned to Old San Juan, where he was given a state funeral and buried at Santa María Magdalena de Pazzis Cemetery, mentioned above.

Capilla del Santo Cristo de la Salud

Visit the Site of a Miracle

The tiny Capilla del Santo Cristo de la Salud (chapel of the Holy Christ of Health) comes with an odd story. The story goes that sometime between 1730 and 1740, during the festival of San Pedro, there was a horse race through the streets of the city, and one of the riders, a Captain Baltazar Montañez y Mujica, missed a turn at this spot, and horse and rider went over the city walls at the spot where the chapel sits. One spectator, Secretary of the Government Tomás Mateus Prats, prayed that the rider would be spared and he did indeed survive the fall. In this version of the story, the chapel commemorates his miraculous survival.

In another version of the story, the rider did not survive the fall, and this chapel was built by Don Tomás to prevent other riders from going over the wall at this same spot. In both accounts… the horse did not survive.

With the construction of the chapel, the name of this street was changed from Calle Santa Catalina to Calle del Cristo.

[video src="https://photos.smugmug.com/USA/Puerto-Rico/San-Juan-Puerto-Rico/i-9t6zRML/0/1e3f98d5/1920/IMG_2810-1920.mp4" /]

Visit Pigeon Park

Pigeon Park is either something you will want to see or something that will make your skin crawl. Right next to the Capilla del Santo Cristo de la Salud mentioned above is a park that has places for pigeons to find shelter in the wall and food that you can buy to feed the pigeons. Be aware that feeding the pigeons looks a bit like reenacting scenes from Alfred Hitchcock’s movie “The Birds.”

Narrow House Old San Juan

Tour the “Narrow House”

La Casa Estrecha used to be an alley between two buildings. As I understand it, the building next door used to be a hotel, and the hotel built this skinny building as a place where the staff could stay. Today the Narrow House is a private residence. How narrow is it? Picture standing in the middle and touching both walls at the same time. This 5′ wide house is so narrow that you have to go outside to have room to change your mind. The house is a two-story house with a living room, dining room, kitchen, bathroom, and bedroom. 

It may be narrow but turn around to see what a beautiful view of the harbor can be had from this house. To arrange a tour of the house, contact the owner Antonio Álvarez. 

(787) 396-5620
ajalvarez.pr@gmail.com

Old San Juan - Santa Ana Church
photo by P. Hughes

See the Church that a Privateer Built

Iglesia Santa Ana was built with money from a wealthy Puerto Rican businessman. That’s not strange, except that the business that he was in was capturing other ships. Miguel Enríquez was a privateer. A privateer is basically a legally sanctioned pirate. During the colonial time period, it was common for countries at war to provide sea captains with letters of mark that allowed them to prey on enemy merchant ships.

Enríquez was originally a shoemaker, but after doing some sales work for the governor, the governor convinced him to become a privateer to help protect the island of Puerto Rico. He commanded a small fleet of up to 30 ships and became quite wealthy from the prize money from captured ships.

Enríquez was a mulatto who was born out of wedlock. This meant that even when he was a wealthy man, he was not welcome to sit in the places of honor in other churches in town. So what did he do? He built his own.

Eventually, he acquired enemies among the powerful men on the island and was accused of smuggling and stripped of his wealth. He took refuge in a Catholic church (this one?). Even though the charges against him were dropped, he died a pauper.

I learned about the connection between Miguel Enríquez and this church in my walking tour. I couldn’t find a lot of corroborating evidence for this story… but it gave me a good excuse to tell you about a privateer.

Banco Popular de Puerto Rico

See an Art Deco Bank

The Banco Popular de Puerto Rico is a lovely Art Deco building in what used to be the center for banking in Puerto Rico. Look across the street in one direction at the red building with a Spanish Tapas restaurant and know that the Lion marked the Bank of Leon at one time. You may still be able to see the Chase bank symbol on the building across the other corner. This area used to be by the main docks for ships entering the area in the Spanish colonial era. Now it is near the cruise ship ports, so the financial center of San Juan has moved on, but it is still a lovely building and one of the more convenient ATM machines in the area.

Mofongo

Find the Best Mofongo

When my daughter and her husband honeymooned in Puerto Rico, they fell in love with the Puerto Rican dish called mofongo. Mofongo starts with smashed plantains and then adds some sort of meat typically. There is a great variety of ways to make and serve mofongo, and I don’t know that I can definitively say who makes the best mofongo as I only tried it at 4 different restaurants. Mofongo is typically served with the ubiquitous ketchup mayo sauce. I don’t know that I became quite as big a fan as my daughter is of mofongo, but I love a good quest on vacation. The one pictured above was from El Balcon Del Moreno across from the Tourist Information Center.

Food Tour Old San Juan

Take a Food Tour

One of the ways to discover the best places to each in Old San Juan is with a food walking tour.  It is a great thing to do early in your trip so that you can learn what you like or maybe what you don’t. I took the Flavors of San Juan food walking tour.  This food tour has 4 different stops:

  • First Stop: Cuatro Sombras (a farm-to-cup coffee house)
  • Second Stop: Patio de Sam (main course)
  • Third Stop: Casa Luna Rest. (another main course and make your own mofongo)
  • Fourth Stop: Anita’s Gelato (enough said)

Along the way, our guide Marjorie Ana suggested other places to eat as well as tidbits of local history.

My tour was paid for by Discover Puerto Rico. Thanks, Discover Puerto Rico!

[tour_widget]food old san juan" data-gyg-q="old san juan walking tour[/tour_widget

Catedral de San Juan Bautista

Catedral de San Juan Bautista

The Cathedral in Old San Juan is the second oldest church in the Americas and the oldest church in the United States. The oldest part of the church can be found in a chapel behind and to the left of the current altar and dates to 1540. The original church, built in 1521, was destroyed by a hurricane.

The entire island that we now know as Puerto Rico was Named San Juan Bautista (Saint John the Baptist) by Columbus, and around the time this church was started, the city was known as Puerto Rico or “rich port.” For some reason, early during the Spanish period, the city and the island switched names. 

There is a memorial in the oldest part of the church about the first event where the people of the island identified themselves as Puerto Rican. So this building is an important part of the Puerto Rican identity.

Old San Juan Cathedral

Notice the dome of the cathedral with its money-saving architectural details painted on instead of constructed. 

Catedral de San Juan Bautista

Inside the cathedral, you can find the tomb of Spanish explorer Ponce de León who was the first governor of the island. There is no evidence from the time that Ponce de León ever searched for the fountain of youth, but he did travel to Florida in 1521 to try and colonize the area for Spain. He was wounded by the local natives in a skirmish, the colony was abandoned, and he died from his injuries. 

You can also find the tomb of the only Roman Catholic cardinal from Puerto Rico, Luis Aponte Martínez, and a shrine to Carlos Manuel Rodríguez Santiago who is the only Puerto Rican to be beatified.

The street directly in front of the city is Caleta de San Juan which runs a short two blocks down to the last remaining gate on the city walls, Puerta de San Juan. Stopping at a city’s cathedral to thank God for a safe voyage was a common practice in an age when crew mortality on a long voyage could easily be 20%. 

 

St Pio, San Juan Cathedral, Puerto Rico

See The Body of a Saint

While Puerto Rico may not yet have a saint of its own, you can see the wax-covered body of Saint Pius in a glass coffin in the cathedral. Saint Pius (St Pio) was an early Christian martyr, a Roman soldier who was killed for his faith. In 1815, the bishop of San Juan, Mariano Rodríguez de Olmedo, wanted a relic for his cathedral, and the Pope gave him the body of St. Pius. The bishop took the body to Spain to have it prepared for display, but for some unknown reason, it was left in Spain until then bishop Pablo Benigno Carrión visited Spain in 1962 and was told he had a saint’s body… apparently in lost luggage.

Old Town Square - Old San Juan, Puerto Rico

Visit The Old Town Square

The tiny park opposite the Cathedral of Old San Juan is the original main square of the city. It is a small square, but you can often find a street musician or a local ice cream vendor at the park. One side of the park is Calenta de San Juan running down to the old town gate. The other side is the Caleta de las Monjas (the way of the nuns).

Hotel Convento

Stay in a Convent

The large imposing building on Caleta de las Monjas opposite the San Juan Cathedral and the old town square is Hotel Convento which is, as the name would suggest, an old convent. Construction started on the convent in 1646. The Monasterio del Señor San José de la Orden de Nuestra Señora del Carmen (Monastery of Saint Joseph of the Order of Our Lady of Mount Carmel) opened in 1851. It was the home of a group of Carmelite nuns. 

In 1903, the convent was closed. The massive building was just too expensive to maintain. In 1959, the heir to the Woolworth fortune, Robert Woolworth, purchased the derelict convent and turned it into a grand hotel. This was part of a large effort to modernize the economy of Puerto Rico called Operation Bootstrap. It should be noted that the rooftop pool overlooking the cathedral was not part of the original convent.

Hotel Convento has two different restaurants, including one in the interior plaza. Even if you don’t stay here, take a quick peek at the interior of the building.

[site22]old san juan[/site22]

Casa Blanca

Visit the Other White House

The oldest house in Old San Juan is Casa Blanca, or “White House.” It was built for the original governor of the Island, Ponce de Leon. The governor/explorer died on his Florida expedition before he was able to live in the house, but his family occupied the house until the middle of the 1700s. The house is now a history museum which is open Tuesdays to Sundays in the morning and in the afternoon, with a break for lunch.

the Piña Colada

Try a Piña Colada

Officially the Piña Colada was invented as a cocktail by bartender Ramón “Monchito” Marrero at the Caribe Hilton in Old San Juan in 1954. But, if you tried one of his Piña Coladas you wouldn’t recognize it. Sure, it had rum, coconut cream, and pineapple juice, but it was served over the rocks. The blended drink that you know and love was invented at the local restaurant Barrachina which still serves the wonderful blended drink. 

La Factoria

Party on Calle San Sebastián

The most lively street in Old San Juan is Calle San Sebastián in the northern part of the city, not that far from El Morro. Here you can find bars like La Factoria, which was named one of the 50 best bars in the world.

In the 3rd week of January, there is a Christmas festival on Calle San Sebastián. The festival celebrates (among other things) the early Christian martyr San Sebastián, so expect to see a few images or statues of a man pierced with arrows. Also, expect to see a few cabezudos or full-head puppets.

La Fortaleza

Visit La Fortaleza

The official name of La Fortaleza is El Palacio de Santa Catalina (the palace of Saint Catherine). It was built as part of the city’s defenses but, since the mid-1800s, has been the governor’s mansion. You can get a 30-minute guided tour of the gardens of La Fortaleza Monday through Friday between 8:15 am and 3:30 pm. A tour must be booked in advance. Depending on what is happening on the day of your visit, you may also get a peek inside the building. The building has housed at least 170 governors of Puerto Rico and is the oldest executive mansion that is still in use in the Americas.

La Fortaleza, the city walls, the fortresses of El Morro, Castillo San Cristóbal, and San Juan de la Cruz comprise the UNESCO site La Fortaleza and San Juan National Historic Site in Puerto Rico.

Plazuela de la Rogativa

Learn the Legend of La Rogativa

At the Plazuela de la Rogativa, you can see an interesting statue of a bishop and 3 women bearing torches. This statue commemorates yet another attack on the city and the legend that surrounds it.

The English again tried to take the city of Old San Juan in 1797 as part of the Anglo-Spanish War (after the French Revolution and only 2 years before Napolean became emperor). The governor of San Juan encouraged a “rogavita” which is a religious procession that comes from the Spanish word to plea. A procession of the bishop and torch-bearing women marched through the streets at night. They started at the Cathedral, and with hymns, bells, and prayers, they pleaded with God to deliver the city. 

The legend goes that their prayers were heard because the British commanders, Admiral Sir Henry Harvey and Lieutenant-General Sir Ralph Abercromby, seeing the procession, thought that it was the arrival of reinforcements and took their 68 ships and 7000 troops and sailed away. Of course… some point out that the stubborn defense by 4000 militia, 200 Spanish soldiers and a ragtag group of 300 French privateers, 2000 armed peasantry, and paroled prisoners might have also influenced that decision, but never let facts get in the way of a good legend.

Plazuela de la Rogativa is situated on a mirador along the old city walls. From there, you can get a good view of La Fortessa and of the only remaining gate of the city, Puerta de San Juan.

Old San Juan, Puerto Rico

Old San Juan, Puerto Rico

Explore the Cobblestone Streets

Old San Juan is known for its Spanish revival architecture and its colorful buildings. The architecture dates back centuries, but the colorful buildings only go back to the 1950s when a serious effort was put into developing Puerto Rico as a tourism destination. Students of history will note that the development of Puerto Rico happens around the same time as the Communist Revolution in nearby Cuba. Before the rise of Castro, much of the U.S. Tourism in the Caribbean was heading to Havana instead of Old San Juan. 

Many, but not all, of the streets in Old San Juan have cobblestones. The oldest of these were brought over to the island as ballast in ships. These same ships were then loaded with gold and other treasures of the new world to return to Spain. 

Plaza de Armas

Sip a Coffee in Plaza de Armas

Plaza de Armas is behind the San Juan Cathedral and the Puerto Rico Department of State building and in front of the SuperMax, which is the only grocery store in Old San Juan. It is known for its beautiful fountain with 4 statues that represent the 4 seasons. 

Plaza de Armas Old San Juan

There are two kiosks in the park where you can get a coffee and a pastry, one of which has some shaded tables to take a break. There are also public restrooms in the park. If those are not open, Marshalls department store next to the park has public restrooms.

statue of Puerto Rican composer Tite Curet Alonso

If you look closely, however, you will see a 5th statue which is a man sitting on a park bench. This is a statue of Puerto Rican composer Tite Curet Alonso (1926 – 2003). Alonso composed 2000 different salsa songs, starting at the age of 15. At least 200 of those songs could be considered hit songs. Alonso moved to New York City in 1960 and lived for the rest of his life on the mainland. When he died, his body was returned to Old San Juan, where he was given a state funeral and buried at Santa María Magdalena de Pazzis Cemetery, mentioned above.

Capilla del Santo Cristo de la Salud

Visit the Site of a Miracle

The tiny Capilla del Santo Cristo de la Salud (chapel of the Holy Christ of Health) comes with an odd story. The story goes that sometime between 1730 and 1740, during the festival of San Pedro, there was a horse race through the streets of the city, and one of the riders, a Captain Baltazar Montañez y Mujica, missed a turn at this spot, and horse and rider went over the city walls at the spot where the chapel sits. One spectator, Secretary of the Government Tomás Mateus Prats, prayed that the rider would be spared and he did indeed survive the fall. In this version of the story, the chapel commemorates his miraculous survival.

In another version of the story, the rider did not survive the fall, and this chapel was built by Don Tomás to prevent other riders from going over the wall at this same spot. In both accounts… the horse did not survive.

With the construction of the chapel, the name of this street was changed from Calle Santa Catalina to Calle del Cristo.

[video src="https://photos.smugmug.com/USA/Puerto-Rico/San-Juan-Puerto-Rico/i-9t6zRML/0/1e3f98d5/1920/IMG_2810-1920.mp4" /]

Visit Pigeon Park

Pigeon Park is either something you will want to see or something that will make your skin crawl. Right next to the Capilla del Santo Cristo de la Salud mentioned above is a park that has places for pigeons to find shelter in the wall and food that you can buy to feed the pigeons. Be aware that feeding the pigeons looks a bit like reenacting scenes from Alfred Hitchcock’s movie “The Birds.”

Narrow House Old San Juan

Tour the “Narrow House”

La Casa Estrecha used to be an alley between two buildings. As I understand it, the building next door used to be a hotel, and the hotel built this skinny building as a place where the staff could stay. Today the Narrow House is a private residence. How narrow is it? Picture standing in the middle and touching both walls at the same time. This 5′ wide house is so narrow that you have to go outside to have room to change your mind. The house is a two-story house with a living room, dining room, kitchen, bathroom, and bedroom. 

It may be narrow but turn around to see what a beautiful view of the harbor can be had from this house. To arrange a tour of the house, contact the owner Antonio Álvarez. 

(787) 396-5620
ajalvarez.pr@gmail.com

Old San Juan - Santa Ana Church
photo by P. Hughes

See the Church that a Privateer Built

Iglesia Santa Ana was built with money from a wealthy Puerto Rican businessman. That’s not strange, except that the business that he was in was capturing other ships. Miguel Enríquez was a privateer. A privateer is basically a legally sanctioned pirate. During the colonial time period, it was common for countries at war to provide sea captains with letters of mark that allowed them to prey on enemy merchant ships.

Enríquez was originally a shoemaker, but after doing some sales work for the governor, the governor convinced him to become a privateer to help protect the island of Puerto Rico. He commanded a small fleet of up to 30 ships and became quite wealthy from the prize money from captured ships.

Enríquez was a mulatto who was born out of wedlock. This meant that even when he was a wealthy man, he was not welcome to sit in the places of honor in other churches in town. So what did he do? He built his own.

Eventually, he acquired enemies among the powerful men on the island and was accused of smuggling and stripped of his wealth. He took refuge in a Catholic church (this one?). Even though the charges against him were dropped, he died a pauper.

I learned about the connection between Miguel Enríquez and this church in my walking tour. I couldn’t find a lot of corroborating evidence for this story… but it gave me a good excuse to tell you about a privateer.

Banco Popular de Puerto Rico

See an Art Deco Bank

The Banco Popular de Puerto Rico is a lovely Art Deco building in what used to be the center for banking in Puerto Rico. Look across the street in one direction at the red building with a Spanish Tapas restaurant and know that the Lion marked the Bank of Leon at one time. You may still be able to see the Chase bank symbol on the building across the other corner. This area used to be by the main docks for ships entering the area in the Spanish colonial era. Now it is near the cruise ship ports, so the financial center of San Juan has moved on, but it is still a lovely building and one of the more convenient ATM machines in the area.

Mofongo

Find the Best Mofongo

When my daughter and her husband honeymooned in Puerto Rico, they fell in love with the Puerto Rican dish called mofongo. Mofongo starts with smashed plantains and then adds some sort of meat typically. There is a great variety of ways to make and serve mofongo, and I don’t know that I can definitively say who makes the best mofongo as I only tried it at 4 different restaurants. Mofongo is typically served with the ubiquitous ketchup mayo sauce. I don’t know that I became quite as big a fan as my daughter is of mofongo, but I love a good quest on vacation. The one pictured above was from El Balcon Del Moreno across from the Tourist Information Center.

Food Tour Old San Juan

Take a Food Tour

One of the ways to discover the best places to each in Old San Juan is with a food walking tour.  It is a great thing to do early in your trip so that you can learn what you like or maybe what you don’t. I took the Flavors of San Juan food walking tour.  This food tour has 4 different stops:

  • First Stop: Cuatro Sombras (a farm-to-cup coffee house)
  • Second Stop: Patio de Sam (main course)
  • Third Stop: Casa Luna Rest. (another main course and make your own mofongo)
  • Fourth Stop: Anita’s Gelato (enough said)

Along the way, our guide Marjorie Ana suggested other places to eat as well as tidbits of local history.

My tour was paid for by Discover Puerto Rico. Thanks, Discover Puerto Rico!

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Old San Juan souvenirs

Shop for a Souvenir

Old San Juan has its share of souvenir shops. Some have tacky t-shirts, but straw hats and colorful dresses are also very popular. The Mundo Taino shops stock goods that are all made on the island instead of being made by the people of China.

Poet's Passage

Hear a Poetry Reading

Right near the Plaza de Armas is an unusual gift store run by local artists called Poet’s Passage. Stop by to see what they are selling or check out their website to see if they have any happenings when you are there. In any case, this is a fun shop to stop at if you are looking for more than a “my parents went to Puerto Rico and all I got was this lousy t-shirt” style souvenir.

Old San Juan

Express your love to San Juan in Plaza Colón

Near the Castillo San Cristobal in the Plaza Colón is a large I heart SJ sign that is popular with tourists who are on Instagram.

Old San Juan Plaza Colon

This plaza marks the spot where the eastern end of the city walls used to end and of the eastern gate for the old city. It is named for Colón, which is to say Christopher Columbus, who discovered Puerto Rico on his second voyage in 1493. The plaza has a tall statue of the explorer.

Castillo San Cristobal

Castillo San Cristobal

Your entrance fee to El Morro will also allow you entrance to Castillo San Cristobal, which was built to protect the city from a land attack. It stood near the eastern gate of the city. Castillo San Cristobal is named for Saint Christopher, who is the patron saint of land travelers. It was built in 1634 following the attack by the Dutch that burned the city in 1625. It was built to prevent that from happening again. It is the largest fortress built by the Spanish in the new world. It is part of the San Juan National Historic Site.

La Perla

Tour Colorful La Perla

Just outside of the old city walls to the north of the city between Castillo San Cristobal and Cementerio Santa María Magdalena de Pazzi is the colorful neighborhood of La Perla. This neighborhood had a justified reputation for being dangerous but is improving in recent years. Still, it might be better to tour it during the day when you can appreciate its vibrant colors. It has an art studio for local artists called Colectivo Perlarte, a mallacon along the water’s edge, and a number of small rustic bars.

Old San Juan Borequa

Live Boricua!

The original name of Puerto Rico before the conquest of the Spanish was Boricua, and that name has been reused now by the tourism board to describe “a way of life, a state of mind, a rhythm and flavor that is distinctly Puerto Rico.” On my latest trip to the island, I arrived only slightly ahead of hurricane Fiona. I came to live to be a temporary digital nomad in Puerto Rico for a week. As I arrived, businesses were shuttering, but the music was still playing. There is something seductive about Puerto Rico, and specifically about Old San Juan.

 Things to do in Old San Juan, Puerto Rico #san-juan #puerto-rico #travel #vacation #trip #holiday #things-to-do #tours

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by Chris Christensen

Chris Christensen is the creator of the Amateur Traveler blog and podcast. He has been a travel creator since 2005 and has won awards including being named the "Best Independent Travel Journalist" by Travel+Leisure Magazine.

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