Thing to Do in Old San Juan, Puerto Rico

History, shopping, beaches, Latin culture, and excellent food- San Juan has something to make anyone happy and is an easy cruise port to explore. It is the oldest city under the US flag. It is a city just asking to be explored by foot, being only 3 square miles large. Here is a step-by-step guide to making the most of your 8 hours in Old San Juan, Puerto Rico. It is also a good starting point if you are lucky enough to be spending a day in this beautiful town and are looking for things to do in Old San Juan.

While visiting the Caribbean Islands, there are constant reminders of their past conquering by numerous European countries and their use as military installations. This may be the most evident in Puerto Rico. Spain conquered this easternmost of the Greater Antilles islands of the Caribbean in the 1600s. It served as a crucial military stronghold to tap into the gold and silver treasures in Mexico, Central, and South America, as well as the perfect gateway to defend and resupply. There are many remnants of fortifications such as guerites (sentry boxes) around town, but the largest fort still intact is the perfect geographic start for our exploring.

Things to Do in Old San Juan, Puerto Rico

1. Take the 10-minute Taxi Ride to Castillo de San Cristóbal.

On this drive, be sure to notice the pretty San Juan capital building on your left before you reach the fort.

This is the most massive defensive fort that Spain built in the new world. It has cool tunnels, an informative museum that will make some sense of the importance of this island to the Spanish and great views of the water and the city. It also has large water cisterns which were used to provide water to the Spanish colonies. My kids especially loved a trip into the dungeon where the walls are marked with a prisoner’s last thoughts.

Entrance into this fort will also gain you entrance into the smaller fort, Castillo San Felipe del Morro, at the end of the day. Be sure to catch the free with admission Tunnel Tour. If you are unable to walk, there is a free bus at the bottom of the hill. It can take you across town to the other fort, but this town is perfect for walking through!

2. Walk Down the Hill to the Plaza Colon.

Christoper Columbus discovered Puerto Rico in 1493. As is true of all the Caribbean islands that the Europeans conquered, the natives, Tainos in this case, were almost completely wiped out soon after his appearance.

Surrounding the plaza is the Tapia Theater, built in 1837, the oldest free-standing building in the US used for drama. Here also is the Antiguo Casino, a beautiful French and Spanish building.

This plaza is a beautiful place to sit and enjoy the sun on your face while enjoying the food at an outdoor cafe, ice cream cart, or food truck. We love Restaurant Raices and the food cart Mofongo. Alcapurrias, ground beef stuffed in cassava and fried, from the food truck was one of my family’s favorite foods that we tried in Puerto Rico. Check out the video at the end of the post to see it.

3. Meander up Calle San Francisco.

Pastel colonial Spanish buildings complete with wrought-iron balconies line the Avenida San Francisco. Take your time strolling and taking in the sights, meandering in and out of the numerous shops, plazas, and churches. If you are staying in town, visit Trip Advisor to find the best hotel to stay in as the perfect starting point for exploring this area in-depth.

At the end of Avenida San Francisco, turn right and head up the hill toward the Catedral de San Juan Bautista.

4. Check Out the Catedral de San Juan Bautista.

This large Cathedral of Saint John the Baptist is where Spanish dignitaries were brought to give thanks for a safe arrival when they visited San Juan. It is free to enter, although an offering is always welcomed. Don’t miss the tomb of Ponce de Leon, the first governor of Puerto Rico, and the mummy of St. Pio.

5. Go Back Down the Hill to the San Juan Gate.

This gate, one of five original ways into this gated city, was where Spanish dignitaries entered the city. Through it, you will find the gorgeous El Paseo del Morro. I loved my whole time in Puerto Rico but especially enjoyed this walk between the outer wall surrounding the city and Puerto Rico Bay. The walk will take you under gargantuan Banyon trees.

A southern journey will take you to the fantastical Raíces Fountain (or Roots Fountain), which tells the historical and mythical story of why San Juan has the flavor and flair of its present incarnation. You can spend hours viewing this fountain from different angles. Be sure to watch this video for a few angles of it.

This fountain sits at the end of Paseo de la Princesa, a gorgeous tree-lined promenade filled with vendors and restaurants.

6. Head Back up the Path to its Northern Terminus to Visit Castillo El Morro.

Finish your touring by exploring Old San Juan’s other fort, El Morro, then head of to dinner or back to the ship dreaming of the day you can return to explore more of this fabulous Caribbean Island with the ease of traveling in the United States.

Have you been to San Juan? What are your favorite sights? Let me know in the comments. If you are headed to Puerto Rico, be sure to check out my trip to Bio Bay, one of my best adventures yet, or 47 Cool Things to do in Puerto Rico!

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