You know trips with kids (or babies) are totally different to solo trips. You have to make sure everybody’s been properly fed, napped (for those who still take daily naps), and entertained. Nobody wants to go on a trip with a sleep-deprived toddler… trust me on this! That’s why I’ve prepared this self-guided San Juan tour for traveling with kids.
I divided this guide into three days, but you can definitely shorten it where you see fit. On days one and two you’ll be seeing Old San Juan because there’s really so much to see, and on day three you’ll see the “newer” part of San Juan and its gorgeous beaches.
Although I’m a beach girl, you’ll see I’m also VERY into history. That’s why I’ll also be giving you a short history of the places we’ll be visiting in this tour.
This is the first post on the “Región Metro” miniseries from my series Bucket List Puerto Rico. Make sure to come back next week for another post about this region.
Day One – Cruising Around the City
Old San Juan, la ciudad amurallada (the walled city). You’d think you’re back in the Colonial period were it not for the massive tapones (what locals call traffic jams) that form EVERY. SINGLE. DAY. Its streets are famous for the adoquines made of blue cobblestone, also used as ballast by the Spanish galleons. The views are stunning and it’s a trip you won’t want to miss!
This guide is assuming you arrived in the morning. Although there’s no real best time to fly with a small child, a good idea is to book a flight near your child’s napping time or right after waking up in the morning. That would be around 9:00-10:00 AM for us, but yours could be much earlier. Some suggest a late flight around your LO’s (little one’s) bedtime, but I know that would be terrible for us. Whenever we’re out around baby L’s bedtime, he gets irritable. But remember, every child is different. If you arrive early, make sure to plan for a nap as your child might be tired from the flight.
Paseo La Princesa
This is a beautiful bayside promenade with the gorgeous Raices (Roots) fountain as its main attraction. The fountain showcases our Taíno, Spanish, and African heritage spectacularly. Note: some parts of the Paseo La Princesa were heavily damaged by recent high tides on March 12, 2018 and are currently under repairs but some areas have now been open to the public. On weekends, you can see a variety of artisans displaying their arts and crafts made out of local materials.
San Juan Gate and La Rogativa
Next, head over to the San Juan Gate. This is a huge red gate which was the old entrance to the city. It’s located at the end of the Paseo La Princesa. The acoustic here is pretty cool, so let your kids have fun with the echo.
After you cross the gate, head up towards the Plazuela La Rogativa at Caleta de las Monjas Street. The sculpture was made in remembrance of the attack by the British in 1797 commanded by Sir Ralph Abercromby. What sets it apart was how the residence defended the city in an almost miraculous way. The soldiers were attending other matters outside of the city and the governor asked the residents to pray to the saints for protection. The women then made a procession with bells and torches, and the British thought they were soldiers and aborted the mission. Some would call that luck, but I know everyone can agree it was genius.
Make sure to take lots of pictures here! You’ll be able to see La Fortaleza (the governor’s mansion, also known as Palacio de Santa Catalina) and get a stunning view of the San Juan Bay. La Fortaleza was the first fortification built to defend the city from invasions. It was built between 1529 – 1537, but it was not considered a good place to guard the city because it was too far from the entrance to the bay. Because of that, it was used instead as the governor’s residence from 1544 and has been ever since.
San Juan Cathedral and Plaza
Head up towards the Plaza de la Catedral (Cathedral Plaza) through the Caleta de San Juan Street. This is a busy place as it’s right next to the Hotel El Convento, the historic 17-century hotel. It was once a Carmelite convent, hence the name, and is now a 4-star small luxury hotel with amazing views of Old San Juan and the bay. I have not stayed here, but I love to admire it every time I go to Old San Juan.
Originally built in 1521 out of straw, the San Juan Cathedral is located at 151 Calle del Cristo. It was destroyed by hurricane San Francisco in 1526 and rebuilt out of wood, stone from La Plata river in Toa Baja and thatch, but it was hit yet again by another hurricane in 1539. Construction continued until 1905 for the building as we see now.
This is the oldest cathedral in Puerto Rico and the second oldest in the Caribbean (preceded only by the cathedral in the Dominican Republic). This Cathedral is home to Juan Ponce de Leon’s remains (governor of Puerto Rico between 1508-1511), Saint Pius (one of the first martyrs of the Roman persecution), and Cardinal Luis Aponte Martínez (first and only Puerto Rican to be elevated to cardinal).
It has endured so many hurricanes, an attack from the Dutch in 1625 that destroyed its library, two earthquakes in 1787, and an attack from the US in 1898 during the Spanish-American war.
You can’t come to Old San Juan and not visit the cathedral!
Checking the Local Scene in the Plazas
Check out some of the city’s plazas. Plaza de Armas is the main square located on Calle San Francisco and the town hall is right across the street. This plaza was used as training facilities by the soldiers. It has a fountain with living statues. Yes, you read that correctly! Some are real statues, but if they didn’t move you’d think all of them were actual statues.
You can take a short pit stop with the littles and visit Señor Paleta, a local ice pop shop located at Calle Tetuan. They have a variety of flavors for the whole family. My favorite is the passion fruit. It almost feels like you’re eating the actual fruit. For the littles’ palates, try the Nutella or brownie flavors. I promise they’ll love it! They don’t have indoor seating but you can enjoy your ice pop at Bastión de las Palmas de San José. It’s a park with benches and a beautiful view of the San Juan Bay.
Another plaza worth visiting is Plaza Colón. It was named after the Spanish conquistador Cristóbal Colón (Christopher Columbus) in 1893 and has a statue of the conquistador. You can see bronze plates on it with important dates in Colón’s life. These plates were made from the cannons the British left in their failed attempt to conquer the city, which adds coolness factor to it I’m sure your kids will love.
If you want to savor the flavors of Puerto Rico, you should have dinner at Raíces. This restaurant features authentic Puerto Rican food and I promise you’ll love it. You can try the mofongo (a dish made with mashed, fried plantain) with anything really, but I prefer the chuleta Kan Kan or the churrasco (steak) with Chimichurri sauce.
Day Two – Hands-On Historical Lesson
So, I really think I should’ve studied history or Caribbean studies instead of politics because I’m fascinated by it. That’s why I included a whole day just for this.
Get an early start and have breakfast at Casa Cortés Choco Bar, located at 210 Calle San Francisco. They seriously have the BEST hot chocolate. It’s a local favorite I promise you and your kids will love. Next up, your first history lesson.
After breakfast, visit Casa Blanca (White House), located in a small corner of Calle San Sebastián. You can take a guided tour or grab a brochure and explore on your own. I know you’ll agree with me when I say this is a hidden gem.
Casa Blanca was the first fortification built in Old San Juan, and it’s the oldest building in Puerto Rico. Built in 1521, it was intended as a home for governor Juan Ponce de León. Unfortunately, he died prior to its completion and never got the chance to live there. However, it served as home to his family and descendants until mid-18th century.
It was then occupied by the Spanish armada. Colonel José Defrusne acquired it to house the engineers who were part of the construction of the famous walls of this city. Later, it housed the US commander to the Caribbean until around 1965, where it was given to the Institute of Puerto Rican Culture. It was then opened as a museum in 1974.
This museum has beautiful gardens, which if you compare it with any pre-hurricane pictures, you’ll see they were pretty badly beaten by the hurricanes in 2017. However, they are still beautiful and you’ll find more than one spot to take beautiful pictures. One of my favorites is the garita (sentry box) close to the entrance. Inside the museum, you’ll find artifacts dated back to the 16th and 17th century and information on the architecture, to give you a sense of how people lived back then.
It’s a hidden gem you won’t want to miss. Plus, did I mention the entrance fee is only $3?! That’s a steal! You can tour the museum in around 30 minutes, but you can definitely stay longer if you want.
Castillo San Felipe del Morro
El Morro, sitting atop a cliff overlooking the entrance to the San Juan Bay, was used to protect the city from pirates and conquerors. The Spanish started construction efforts in 1539, but construction ran until 1787.
It was center stage to attacks from the British in 1595 and 1598, this last one by the Earl of Cumberland who conquered but couldn’t hold it for long; the Dutch in 1625 who invaded from land, which prompted the construction of the walls; and the US Navy in 1898 during the Spanish-American war. This last attack destroyed the lighthouse and made it evident the walls were no match for US technology. If you visit, you’ll see the lighthouse doesn’t quite “fit in” with the rest of the fortification because it was rebuilt later.
Because of its prime spot, it has beautiful views of the ocean. Take time to bask in the views, and take pictures next to the cannons used to defend the city. Also make sure to take pictures of the garitas from which soldiers stood their watch.
After your tour of the fort, make sure to take some time to fly a kite with the kiddos in the fort’s lawn. Because of the trade winds, this is THE BEST place to fly a kite in Puerto Rico.
Plaza del Quinto Centenario and Cuartel de Ballajá
This plaza was built to commemorate the 500 years of the discovery of America and is one of the newest plazas in the city. Make sure to take pictures at the Totem. Grab a piragüa, a beverage made of shaved ice and the syrup of your choice, from a local piragüero. My favorite has always been frambuesa, but tamarindo is also a local favorite. You can usually find one right next to the Plaza.
Then it’s off to Cuartel de Ballajá, which was built by the Spanish armada between 1854 and 1864. It was once used as infantry barracks and housing for around 1,000 soldiers. After 1898, the US also used it as barracks until 1939 when it was converted to a hospital.
In 1976, the Puerto Rico government acquired the building and it’s now center stage to many cultural events. You can also find the Museo de las Americas on the second floor. If you have time and your kids aren’t too hungry or tired, take a look inside. You’ll find exhibitions on the Puerto Rican culture and the Americas.
Lunch and a Nap
You can grab a quick bite at Don Ruiz, a cozy cafe on Ballajá, or head back to he hotel room (or AirBnB) for lunch and a nap. This would not be a guide for moms if I left out nap time. Trust me! Even my 9-year-old stepson takes them occasionally, especially if we’ve been walking for a long while.
Castillo San Cristobal
After a much-needed pit stop, you’ll definitely want to visit San Cristobal. It was built to guard the land entrance of the city. Construction started in 1634 and like El Morro, took quite a while to be completed (until 1790). The attack from the Dutch in 1625 prompted the construction of this fort.
With this fort, El Morro and the city walls, the Spanish made San Juan virtually unconquerable. However, the attack of 1898 proved that you always need to stay up to date with the latest technologies. The forts and walls were no match to the technology of the US Navy.
Like El Morro, this fort has amazing views of the ocean and the city. Make sure to take lots of pictures!
One of the highlights are the underground tunnels and the galleons painted on the dungeon’s walls. But the main highlight is the Garita del Diablo (the Devil’s Sentry Box). Legend has it that soldiers would mysteriously disappear here.
As a side note, I’d suggest you wear good walking shoes. The tunnels can get slippery, especially the steep ones. You can take your baby carrier to make sure your little one is safely in your arms, but it can also get hot, so I’d also suggest to take a stroller just in case it gets too hot.
Another thing to note is that this is the largest of the two forts, so make sure to allow 3 hours to explore all of it.
Next, you’ll have time to stop at El Capitolio (the capital building). After some controversies over how it should be built, construction began in 1925. In fact, Luis Muñoz Rivera, the author of the bill, died in 1916 without seeing the bill pass.
Politics in the island have degraded in the past years and unfortunately, it’s more of an eyesore to some people, but I can’t deny that it’s a beautiful building. It has a marble stairway, magnificent columns, and it houses a copy of the Constitution of Puerto Rico.
Make sure to take pictures of the Plaza San Juan Bautista right across the street. It has a statue of San Juan Bautista (John the Baptist, the patron saint of the city) and different levels with benches to sit all around. You can also find a mosaic of each town’s shield and Puerto Rico’s flag. This is also a great place for you to take in the views of the ocean. You will also see people running and biking, as a bicycle lane was recently added.
You can choose to go to any of the restaurants over at SoFo (short for South Fortaleza). This spot is famous for the culinary fest held every year in late May. You can savor the flavors of Puerto Rico in up to 40 restaurants. One of my favorite restaurants is Vaca Brava. A local favorite plate from there is El Tendedero (the clothes line), where they put assorted meats and chicken on a rod, simulating a clothes line. This is a plate you’ll want to share with the family. It’s massive!
Day Three – Beach Hopping
There are two beaches I believe you should try to visit if you have a third day to spare. You can always stick to one if you think it’s too much of a hassle to move the kids around once they have gotten comfortable with the beach, but these are just too nice to pass up. Make sure to bring sunscreen and reapply every couple of hours. Don’t let the kiddos to get sunburned!
El Escambrón Beach
This beach is located right outside Old San Juan by Luis Muñoz Rivera Avenue. However, if you’re staying at Old San Juan, you’ll want a rental car or a taxi (although a rental will be much cheaper).
El Escambrón Beach is a favorite spot due to its beautiful views of the ocean and the Castillo San Cristobal at the distance. It has parking inside for a cost, or you can park outside near the Juan Ponce de León Avenue for free. It’s really just a short walk and nothing beats free!
Take some time to take pictures at the Fortín del Escambrón, which was also a fortification built by the Spanish army to defend the city from conquering armies.
You have two options here: the Playita del Condado and Ventana al Mar Park, both on Ashford Avenue. If you have small children, I’d recommend going to Playita del Condado. It’s a smaller beach with very few waves, great for smaller children. However, Ventana al Mar has more restaurants to choose from. Plus, you’ll find a Ben & Jerry’s there!
As for a nap, you’ll probably find that your LO will sleep comfortably at the beach. There’s just something about the sound of the waves that is so soothing and relaxing. Don’t worry about going back to the hotel until you’re ready call it a day.
So there you have it! There is so much more to see, but I think I covered the most important ones. What do you think about this tour? Would you add anything to it? Tell me what you think in the comments section below!
Disclaimer: Some of the links in this post are affiliate links. This means that if you make a purchase, I will receive a small commission at no extra cost to you. This will help this site stay online. I participate in the Amazon Services LLC Associates Program. Thanks for your support!
And don’t forget to sign up for the newsletter to receive updates about new posts in this series!