10 Things to Do in Old San Juan

10 fun things to do in Old San Juan … from exploring the colorful streets to eating delicious Puerto Rican food, these are the best activities in this historic, colonial city!

10 Fun Things to Do in Old San Juan, Puerto Rico! This Old San Juan travel guide is filled with tips and things to see in this historic, colonial city, including visiting the forts, checking out the colorful architecture, enjoying delicious Puerto Rican restaurants, and even spotting the famous stray cats! | Hello Little Home

Have you been following my adventures in San Juan, Puerto Rico?

From relaxing on Isla Verde Beach to exploring the San Juan National Historic Site to indulging in lots of delicious food, it was such a fun trip. Looking back, I’m amazed that I saw all these wonderful places in just 48 hours!

I’m wrapping up this series with my favorite things to do in Old San Juan … no trip to San Juan is complete without a visit to this historic neighborhood!

10 Things to Do in Old San Juan

Before we jump into all the best things to do in Old San Juan, let’s talk history.

Old San Juan is the historic, colonial section of the city of San Juan, and it’s the oldest city under U.S. jurisdiction. Christopher Columbus landed in Puerto Rico in 1493 during his second voyage, and in 1508, Juan Ponce de León was appointed as the first governor of the island. Are those elementary school history lessons ringing any bells, yet?

San Juan itself was founded in 1521 when the original Spanish settlement was moved to the current location of Old San Juan, a small island on the north coast of Puerto Rico. To protect this city (an important gateway to the New World), the Spaniards built forts and walls around the city.

Many of these fortifications still stand today, and they surround colorful Old San Juan, which is filled with beautiful old buildings, museums, restaurants, shops, and so much more

Okay, enough history … are you ready to start exploring this gorgeous city? Here are my favorite things to do in Old San Juan!

1. Wander the Colorful Streets

Colorful Buildings in Old San Juan | Hello Little Home

By far, my favorite thing to in Old San Juan is simply to wander the colorful streets.

Down almost every street, you’ll find beautiful colonial Spanish architecture … much of which has been painted in a vibrant color palette ranging from pale pastels to bold turquoises, pinks, and yellows.

It’s just so darn pretty!

Beautiful street in Old San Juan | Hello Little Home

As you walk around Old San Juan, you’ll be surrounded by colorful, tile-roofed buildings.

Look for details like ornate balconies, arched doorways, and heavy wooden doors. Hiding behind many of those gorgeous doors are inner courtyards … wouldn’t you love a peek inside?

Make sure to stop and look up every once in a while. You will be rewarded!

Colorful Building in Old San Juan with Juliet Balconies | Hello Little Home

Many of these historic buildings were first restored in the 1940s, and the work has continued since then (including a major refurbishing for the Columbus Quincentennial in 1992).

Although most of these buildings are occupied, I spotted quite a few vacant buildings during my walk.

It will be interesting to see how the city continues to evolve on future visits.

Colorful Street in Old San Juan | Hello Little Home

Because the streets of Old San Juan are so narrow and congested with traffic, I would avoid driving there if at all possible.

The best way to see the streets is by walking them. Keep in mind that Old San Juan is very hilly. Make sure to wear comfortable, flat shoes as you’ll be walking up hills and over cobblestone streets.

If you don’t want to walk, you can catch a free trolley at various spots throughout the city.

Colorful Buildings and Blue Cobblestones in Old San Juan | Hello Little Home

Old San Juan is filled with restaurants and shops … many of which are pretty touristy.

You’ll find everything from chains (I spotted a Wendy’s and a Walgreens, among others) to local spots.

I didn’t do a lot of shopping, but I did stop into a cute shop called Eclectika right by Plaza Colón. It was filled with beautiful jewelry and home decor items. Perfect if you want a souvenir that you’ll actually use.

Colorful Buildings and Blue Cobblestone Street in Old San Juan | Hello Little Home

Colorful Building and Door in Old San Juan | Hello Little Home

2. Relax in a Plaza

Christopher Columbus Statue in Plaza Colón in Old San Juan | Hello Little Home

Old San Juan is filled with plazas and parks. Each one has a story, and they’re the perfect place to relax, cool off, and enjoy a bit of local life.

As I started exploring the city, I took a quick detour into Plaza Colón. It’s located near Castillo San Cristóbal, one of the historic forts, and features a statue of Christopher Columbus.

When I exited the plaza, I saw something that struck a little fear in my heart … a large gathering of pigeons. Birds freak me out, so I didn’t waste any time beating a hasty retreat.

Pigeons in Plaza Colón in Old San Juan | Hello Little Home

I spotted pigeons in many of the plazas I visited, but one is especially known for these birds: Parque de las Palomas.

Palomas is Spanish for pigeons, and when I walked by there, it was thronged with hundreds of birds. If you don’t have a bird phobia like I do, you might enjoy this plaza, and I’m sure kids would love it.

As soon as I saw the pigeon plaza, I picked up the pace … ha ha. I’d much rather spend my time in Plaza de Armas, pictured below.

Plaza de Armas in Old San Juan | Hello Little Home

Plaza de Armas is centrally located … it’s the city’s main square.  Over the years, it’s been used for everything from military parades to a vegetable market.

This plaza is home to four 100 year old statues representing the four seasons. You can see them surrounding the fountain below with Old San Juan’s city hall, Casa de Ayuntamiento, in the background.

Plaza de Armas is the perfect spot to take a break, and there’s even a stand selling drinks near the city hall.

Plaza de Armas in Old San Juan | Hello Little Home

My favorite plaza was the one I found along Calle del Cristo across from the Cathedral of San Juan Bautista (one of the oldest buildings in San Juan).

I’m not sure what the name of this plaza is, but it was so peaceful and quiet.

The plaza is surrounded by colorful buildings, and it’s located just up the street from the San Juan Gate.

Plaza along Calle Del Cristo in Old San Juan | Hello Little Home

This plaza is shaded by trees and filled with quirky statues.

Grab a seat and relax for a few minutes!

Statue in Plaza along Calle Del Cristo in Old San Juan | Hello Little Home

Plaza along Calle Del Cristo in Old San Juan | Hello Little Home

Seriously, how much more beautiful can it get?

I could have sat here all day, but there were more sites to see!

Colorful plants and buildings by Plaza along Calle Del Cristo in Old San Juan | Hello Little Home

Next up is Plazuela de Rogativa, which features a large bronze statue commemorating the 1797 siege by Sir Ralph Abercromby.

To ward off the invaders, women of the town carried torches and rang bells as they proceeded through the streets of Old San Juan led by the city’s bishop. British soldiers mistook the commotion for reinforcements from Spain and sailed away.

Personally, I would have been scared off, too. The statue makes an imposing impact.

Rogativa is located on a hill above the San Juan Gate and is a great place to take in San Juan Bay.

Monument in Plazuela de Rogativa in Old San Juan | Hello Little Home

Monument in Plazuela de Rogativa in Old San Juan | Hello Little Home

Another plaza I stopped in was located along Calle Norzagaray near Castillo San Felipe del Morro, one of the historic forts.

It was so hot and humid the day I spent in Old San Juan, and I was able to buy a bottle of water here and cool off.

If you face the other way in this plaza, you’ll have a beautiful view of the Atlantic Ocean.

Plaza along Calle Norzagaray in Old San Juan | Hello Little Home

The final plaza I visited on my trip was Plaza del Quinto Centenario, which also has views of El Morro and the Atlantic.

This plaza was built in 1992 and commemorates the 500 year anniversary of Columbus’ first voyage. As I’ve mentioned, Old San Juan is hilly, and the plaza’s  totem (seen below) is located on the highest point in the city.

The totem was constructed of black granite and features ceramic replicas of archaeological artifacts.

Plaza del Quinto Centenario in Old San Juan | Hello Little Home

Plaza del Quinto Centenario in Old San Juan | Hello Little Home

3. Explore a Historic Fort

View of the historic entrance to Castillo San Cristóbal, part of the San Juan National Historic Site and one of the best things to in San Juan, Puerto Rico! | Hello Little Home

If I had to choose, visiting the historic forts surrounding Old San Juan was probably my favorite part of my San Juan trip.

Whether you’re a history buff or not, no trip to Old San Juan is complete without visiting its historic fortifications (which include 3 forts, the city wall and San Juan Gate, and the Paseo Del Morro trail).

Since I’ve already written so much about these sites, I won’t go into detail here. But do make sure to check out my post about the San Juan National Historic Site for more information, plus lots of photos and fun details.

4. Look Down at the Blue Cobblestones

Blue Cobblestones in Old San Juan | Hello Little Home

As you explore Old San Juan, make sure to look down, because many of the streets are paved with blue cobblestones!

The cobblestones were originally used as ballast to help ships sailing from Europe maintain their stability as they crossed the ocean. Once the sailors arrived in Puerto Rico, the stones were discarded and residents used them to pave the streets.

Over time, exposure to weather and traffic has given the cobblestones (which are made of iron slag) their characteristic shiny blue-gray hue.

I spotted these colorful cobblestones on Calle del Cristo and in the surrounding streets.

Blue Cobblestones in Old San Juan | Hello Little Home

5. Count the Cats

Stray Cat in Old San Juan | Hello Little Home

One thing I wasn’t expecting to see in Old San Juan was all the stray cats, but apparently, it’s a thing!

As I explored the city I spotted a cat here and there, but didn’t think much of it. Once I walked through the San Juan Gate and along the Paseo del Morro though, it seemed like I started seeing them everywhere!

The cats have been around for a long time, and apparently, they were originally brought in to rid Old San Juan of rats. As the rat population died down, the cat population multiplied.

If you want to check out these cats, you can see them on the city streets or along the Paseo del Morro.

White Gates in Old San Juan | Hello Little Home

I also spotted a ton along the road by Plazuela de Rogativa. Just look for the white gates and keep walking.

This road will lead you to El Morro (one of the historic forts), and you’ll see lots of cats along the way. You’ll pass pretty palm trees and buildings, too.

There’s also a playground along this road, which would be a good pit stop if you have kids.

Palm Trees in Old San Juan | Hello Little Home

I took a quick detour to check out Casa Rosa. It was built in 1812 to house troops assigned to the San Agustin Bastion and was converted to an officers quarters in 1881 by the Spanish Army.

Later it was used as a museum, and today it operates as a day care center for the children of federal employees.

And of course, there was a cute kitty just inside the gate!

Stray Cat in front of Casa Rosa in Old San Juan | Hello Little Home

As the population of stray cats increased over the years, a number of people wanted to get rid of them, and an organization called Save A Gato sprang up to save them.

Save a Gato captures the feral cats, then spays or neuters them before returning them to the Paseo. They also offer some of the cats for adoption and provide feeding stations for the cats.

Residents of Old San Juan put out food for the cats, too.

Stray Cat in Old San Juan | Hello Little Home

As you continue to walk along, you’ll pass some colorful old buildings, as well as cats.

This one holds a conservation workshop for the old buildings.

Colorful Building in Old San Juan | Hello Little Home

As you wind around the corner at the end of the road, you’ll see El Morro.

Another building we passed in this area was full of cats peeking out from behind a gate. I think it was a sanctuary.

Stray Cats in Old San Juan | Hello Little Home

After eating dinner near El Morro, we headed back along that same road toward Rogativa and the San Juan Gate and spotted this kitty.

Not a bad life, eh?

Stray Cat in Old San Juan | Hello Little Home

6. Enjoy the Street Art

Part of a 450-feet-long mosaic mural honoring Felisa Rincon de Gautier, mayor of San Juan from 1946 to 1969. | Hello Little Home

One of my favorite things to do in Old San Juan (and on any trip really!) is to discover street art. It’s fun to look at, of course, but it often reflects the culture and politics of the city, too.

My husband drove me to Old San Juan before heading off to work, and we passed the mural above on our way in.

It’s part of a colorful 450-feet-long mosaic honoring Felisa Rincon de Gautier, the mayor of San Juan from 1946 to 1969. Love those glasses!

Street Art in Old San Juan | Hello Little Home

The colorful Liga de Arte building above also featured a mural.

It’s located near Plaza del Quinto Centenario.

Street Art in Old San Juan | Hello Little Home

After an evening cocktail at La Cubanita, we spotted the door and mural below nearby.

The door is a famous tourist photo spot, and it originally featured the colors of the Puerto Rican flag. A group of artists recently painted the flag black and white to protest the approval of the Puerto Rico Oversight, Management, and Economic Stability Act, also known as PROMESA.

PROMESA was passed by the U.S. Congress, and signed into law by President Obama, and it was promoted as a way to manage Puerto Rico’s more than $70 billion of debt. However, it has severely undermined the island’s political autonomy. One of its measures, for example, decreased the hourly minimum wage in Puerto Rico to $4.24 (about $3 less than the US federal minimum wage).

Black and White Puerto Rico flag painted on an old door in Old San Juan | Hello Little Home

The door is surrounded by lithographs of famous Puerto Rican artists made by the collective Grabadores por Grabadores.

Street Art in Old San Juan | Hello Little Home

I spotted that black and white flag hanging on a few buildings around the city, including the one below in Old San Juan.

The issues surrounding the relationship between the U.S. and the commonwealth of Puerto Rico are complex. Puerto Ricans are U.S. citizens, and they can fight in our wars. Yet, they cannot vote for our president. They also don’t have full representation in our government, and the commonwealth doesn’t receive the same benefits that U.S. states do.

In June 2017, Puerto Ricans overwhelmingly voted in favor of statehood, yet only 25% of people eligible to vote did so (with many people boycotting the referendum). And even if a majority of Puerto Ricans had turned up and voted in favor of becoming a state (they could also vote to keep the same relationship or become independent), Congress would still need to approve it, which seems unlikely.

If you want to learn more, this article has a good overview, and keep an eye on the news, because there’s another vote coming up in October 2017.

Building with Black and White Puerto Rico Flag in Old San Juan | Hello Little Home

7. Enjoy Beautiful Water Views

Looking over the historic wall in Old San Juan | Hello Little Home

Old San Juan is situated on an island. Wherever you go, you’re surrounded by water whether it’s the Atlantic Ocean or San Juan Bay.

There are many opportunities to walk along the water, such as on the Paseo del Morro, the Paseo de la Princesa, or even on the outer defenses of Castillo San Cristóbal.

You can also see it from above by peeking over the historic city wall … beautiful, right?

Beautiful view of San Juan Bay | Hello Little Home

I loved watching the Atlantic near El Morro (one of the forts). We even saw a cruise ship coming into the harbor.

The grass was filled with families flying kites, too.

Wherever you go in Old San Juan, take the opportunity to enjoy the gorgeous water views that surround you!

View of Atlantic Ocean Near El Morro Fort in Old San Juan | Hello Little Home

8. Enjoy Delicious Puerto Rican Cuisine

Line outside Señor Paleta in Old San Juan | Hello Little Home

Of course, one of the best things to do in Old San Juan is to enjoy delicious Puerto Rican cuisine!

Puerto Rican food has been influenced by a variety of cultures, including Taíno Arawak (the original inhabitants of the islands), Spanish, African, and American, and it uses indigenous seasonings and ingredients such as coriander, papaya, cacao, nispero, apio, plantains, and yampee. The mingling of these flavors and ingredients has resulted in modern day Puerto Rican cuisine.

You can find everything from classics like mofongo to more gourmet dishes in Old San Juan. There is a restaurant to satisfy every craving.

I’ve enjoyed Puerto Rican food a number of times before visiting the island. And although I’ve never met a plantain I didn’t like, I never found Puerto Rican food to be very vegetarian friendly either. A girl can’t live on plantains alone … or can she? 😉

Thankfully, I didn’t have any problems finding veg-friendly spots in Old San Juan, and I even discovered a number of vegetarian / vegan restaurants throughout the city. And of course, meat and seafood eaters like my husband will be very happy there, too!

Inside of Señor Paleta in Old San Juan | Hello Little Home

Unfortunately, I didn’t get to try many restaurants in Old San Juan since my time was so short. But I loved the ones I did try!

As I’ve mentioned a time (or ten!) before, it was hot while I was in San Juan. So my first stop was Señor Paleta.

It really doesn’t get much cuter than Señor Paleta, and their popsicles are delish, too. This petite shop is very popular, but I arrived at just the right time, and the line wasn’t too long.

I knew going in that I wanted to get guayabana (guava). It was the perfect afternoon treat.

Guayaba paleta from Señor Paleta in Old San Juan | Hello Little Home

My husband was working, and I wasn’t sure what time he’d be able to meet up. That paleta and a pastry from Starbucks, where I stopped in to charge my phone, were my lunch.

By the time we finally met up in late afternoon, both of us were starving. I’d created a Yelp-sourced list of possible restaurants in advance, but we ended up picking the closest restaurant in sight: Cinema Bar 1950. And thankfully, it ended up being a good choice!

Cinema Bar 1950 serves Puerto Rican food with a modern spin, as well as delicious cocktails. It’s located in the Museo de las Américas building.

Inside of Cinema Bar 1950 in Old San Juan | Hello Little Home

The decor has a fun vintage movie theme, and it would be the perfect place for a meal after visiting the museum or El Morro, which is right nearby, too. I spotted a couple ladies enjoying an after work cocktail at the bar, too.

They also show local and international films.

Inside of Cinema Bar 1950 in Old San Juan | Hello Little Home

As far as food goes, we went all in!

Ha ha …

Table full of food at Cinema Bar 1950 in Old San Juan | Hello Little Home

Cinema Bar 1950 has a wide selection of entrees on their menu, as well as a number of smaller plates, and we went the tapas route.

We got a delicious salad topped with fried cheese, beans and rice, mofongo, an antipasto plate, and Joel had some ceviche. It was all very tasty, especially since we picked this place totally randomly!

Between the atmosphere and the yummy food, I would definitely return on a future visit.

Mofongo and Salas at Cinema Bar 1950 | Hello Little Home

After leaving Cinema Bar 1950, we walked around the plaza of the Museo de las Américas for a while. It was so pretty.

You can find public bathrooms just off the plaza, and there’s a coffee shop, too.

Museo de las Americas Plaza in Old San Juan | Hello Little Home

9. Take a Moonlight Stroll

Moonlight view of Paseo la Princesa | Hello Little Home

Old San Juan has such a charming and romantic atmosphere. If you’re visiting with your sweetie, make sure to take an evening stroll around the city.

My top choice would be Paseo de la Princesa, which is right along the water. It’s so beautiful at night with the lanterns lit … we were there just as the sun was setting.

Of course, wandering around the colorful streets while stepping across those famous blue cobblestones is a pretty romantic choice, too!

Colorful Buildings in Old San Juan as sun sets | Hello Little Home

10. Relax with a Cocktail

Mojitos at Cinema Bar 1950 in Old San Juan | Hello Little Home

Before you head back to your hotel, stop by one of Old San Juan’s many bars for a cocktail. Love dancing? You’ll find plenty of live music, too.

Our waiter at Cinema Bar 1950 said they were known for their flavored mojitos, and we couldn’t resist. My husband had a coconut mojito and mine was watermelon … both were delicious.

When it comes to cocktails though, our favorite discovery was La Cubanita. The bar is housed inside what used to be a store, and you can see a photo of the original owner above the bar.

This place had so much character, and our bartender was a true cocktail craftsman. They didn’t have everything needed to make the drink I ordered, so the bartender asked me what I liked, then made a drink just for me. It was amazing!

La Cubanita is a wonderful spot for a expertly crafted cocktail, and since they have a kitchen, it’s pretty much the perfect late night destination!

La Cubanita Bar in Old San Juan | Hello Little Home

Tips for Exploring Old San Juan

I hope you enjoyed reading about my favorite things to do in Old San Juan! You can definitely see all of these sites in one day, like I did. For a more relaxed time, I would plan on two days though, especially if you want to linger at the forts.

Here are some tips for making the most of your visit to Old San Juan:

  • History – Old San Juan is filled with beautiful colonial architecture and historic sites. You’re sure to appreciate everything you see more if you learn some of the history before you visit. The National Park Service has a good overview. You can also read more about the Taíno Indians who called the island home before Christopher Columbus landed.
  • Getting Around – If you can, I recommend exploring Old San Juan on foot. It’s compact and highly walkable, although it is hilly. Don’t have a lot of time or would rather not walk? Take the free trolley instead. Just don’t drive; the streets are narrow and super congested.
  • What to Wear – Make sure to wear comfortable shoes, as well as lightweight clothes if you’re visiting in summer (it’s hot). I wore a dress and flat, comfy sandals, which was perfect. Slather on the sunblock and wear a hot, too, if you want to avoid a sunburn.
  • Shopping – Old San Juan is filled with shops selling everything from cheap souvenirs to pricey Harry Winston rings. Skip the coffee mug and buy something more unique like locally-made jewelry, cigars, candy, coffee, or rum. You’ll find shops throughout Old San Juan, however many are concentrated on Fortaleza Street, Cristo Street, and San Francisco Street. I especially enjoyed Eclectika, which is located near Plaza Colón.
  • Food and Drink – I didn’t have nearly enough time to enjoy Old San Juan’s many restaurants. One thing is for sure though, you will not run out of options! Many restaurants are located along Calle Fortaleza, but don’t limit yourself to that one street (and make sure to check out Yelp! before you stop in anywhere for reviews). My favorites were Señor Paleta, Cinama Bar 1950, and La Cubanita.
  • Stray Cats – Learn how you can help (or maybe even adopt) the feral cats of Old San Juan by visiting Save A Gato.
  • Plaza and Parks – No trip to Old San Juan is complete without visiting one of the many beautiful plazas. Tour Old San Juan has lots of helpful information.

 

10 Fun Things to Do in Old San Juan, Puerto Rico! This Old San Juan travel guide is filled with tips and things to see in this historic, colonial city, including visiting the forts, checking out the colorful architecture, enjoying delicious Puerto Rican restaurants, and even spotting the famous stray cats! | Hello Little Home

Did you enjoy reading about all the fun things to do in Old San Juan?

Please share this post, then make sure to check out all of the highlights from my trip to Puerto Rico!

  • Part 1: 48 Hours in San Juan Puerto Rico … tips for visiting San Juan, plus the Museo de Arte de Puerto Rico, the Santurce neighborhood, and a fun foodie find!
  • Part 2: Isla Verde Beach … all about beautiful Isla Verde Beach in Carolina, Puerto Rico + the best places to stay in San Juan.
  • Part 3: San Juan National Historic Site … this amazing U.S. National Park and World Heritage Site is a must see when visiting San Juan!
  • Part 4: Old San Juan … you’re here!

Have you ever visited Old San Juan?

P.S. Check out all of my travel stories for more vacation inspiration!

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