A Day in Old San Juan, Puerto Rico


La Rogativa at Plazuela de la Rogativa

San Juan, Puerto Rico is recognized as one of the oldest cities in the New World.  Founded around 1508, it soon became the jewel in the Spanish Crown for its strategic location and profitable crops.  Today’s San Juan is a modern city but luckily you can still experience its 500 year-old heritage in the Old San Juan district.


19th Century Santa María Magdalena de Pazzis Cemetery


Puerto Rico has a rich cultural diversity stemming from its first known inhabitants, the Taino Indians, who can be traced back to 1000 A.D.  These hunter-gatherers lived in small villages and survived on a diet of indigenous pineapples, cassava, sweet potatoes and of course seafood.  

Jump to 1493 when Christopher Columbus arrives on the island and claims it for Spain, renaming it San Juan Bautista (Saint John the Baptist).  Then in 1508, along comes Juan Ponce de León who helps to colonize the island.  The Spanish enslave the Taino people, assigning them to work wage-free for the colonists.  Disease and mistreatment cause the Taino population to diminish.  They rebel against the well-armed Spanish but are unsuccessful and the remaining survivors flee into the mountains or off the island.


With no Taino to work, the Spanish bring African slaves to work the mines and the plantations in 1513.  Sugar becomes an important cash crop and later coffee is introduced.  The Spanish essentially remained in power until the Spanish-American war in the 19th century, after which the U.S. acquired it in the Treaty of Paris. In the 20th century, tourism was added to it list of attractions and people travel to the island to enjoy its tropical climate, beautiful beaches and lush mountains.


You can still feel the echo of military battles, pirate attacks and ecclesiastical inquiries in the district’s narrow opalescent cobblestoned streets and well-preserved colonial architecture not to mention the centuries-old fortifications.


The Spanish Inquisition also touched this part of the New World and its first headquarters was located in what is now Old San Juan.  With a “convert to Catholicism or die” motto, many churches sprang up in the town and some are still standing today.

The district itself is not very big, only seven square blocks, which is all the more reason to take your time exploring its lively street life, good rum and colorful history.  Many visitors stay in the resort neighborhood of Condado, which is just a couple of miles away, and travel to the district for the day.

For literary buffs, Old San Juan is also the setting of the book, The Rum Diary by Hunter S. Thompson.  The protagonist in the novel is a writer, who like its author, moved to San Juan to work for a paper (the character: The Daily News, Thompson: a small sports newspaper).  Rumor has it that the novel was written in the 60’s but not published until 1998, after his friend Johnny Depp discovered it in his papers.  Depp later starred in the 2011 film after Thomson’s death in 2005.


I was only able to visit this most picturesque of towns for a few hours on a recent visit but was lucky enough to be there during the SOFO culinary festival.  Over the course of four nights, forty restaurants offer eight stages with live music and of course great food and drink.


Food enthusiasts can either opt for more formal dinners inside the participating restaurants, check out the grab-n-go options at the kiosks, or settle in for some good people watching at the al fresco tables set up around the festival.  I ate in at the popular Parrot Club (363 Calle Fortaleza) where the passion fruit cocktails, ceviche and the carne Y yuca fritas (yuca fries with pulled pork) were a tasty reason to visit here again.


Fort San Felipe del Morro was named in honor of King Philip II of Spain.  This fortification was designed to guard the entrance to the San Juan Bay, and defend the Spanish colonial port city of San Juan from foreign enemies.  A UNESCO World Heritage Site, the massive fort is Puerto Rico’s top visitor’s attraction but it is so big that you don’t have to worry about crowds.

Castillo de San Cristóbal is a fortification that was built in the 18th century and covered over 27 acres sealing the city of San Juan.  It was partially demolished in the 19th century when the city no longer needed its protection.  You can still pass through the original gates to the city.

La Fortaleza, also known as the Palacio de Santa Catalina, is the oldest official executive mansion in continuous use in the Americas.  Built between 1533 and 1540 to defend the harbor of San Juan, it is currently the residence of the Governor of Puerto Rico.  Visitors can take free guided tours through the 40-room mansion and surrounding battlements that were used to defend against foreign invaders.  It is generally open weekdays from 9-4pm and has special events during the Christmas holidays for children.

P1000436Plazuela de la Rogativa – is marked by the famous La Rogativa bronze sculpture.  According to historical accounts, in the 18th century, British troupes took control of the city through a naval blockade.  The San Juan governor ordered a “rogativa” (public prayer made to God to get a serious need for remedy).  Lead by the bishop, the women of the city marched through the streets at night singing hymns, carrying torches, bells, and praying for their city to be saved.  According to legend, the British mistook the sights and sounds of that night as evidence that reinforcements were there and abandoned the city.

San Juan Cathedral is a 450 year old church. Ponce De Leon is interred here. The artwork on the ceilings has been recently restored  – go in and take a look but be respectful as mass is still held here.

Galeria Nacional (National Gallery) is housed in the restored Saint Aquinas monastery of the Dominican Order and is reputed to be one of the first significant pieces of architecture built in Puerto Rico.  You can learn a great deal about people through their art and here you can see over 150 pieces from Puerto Rican artists from the last few centuries.

For maps and directions, a visitor’s center is located across from the Plaza de la Darsena and is open everyday from 9:00am until 5:30pm.


One response to “A Day in Old San Juan, Puerto Rico

  1. Pingback: Why San Juan's Condado Plaza Hilton is a Great Family Destination - Traveling Mom·

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