Sep 23, 2022

Travel Inspiration

The Top 16 Things to Do in Old San Juan

Fora Author Fora Travel

The Modern Travel Agency

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San Juan Puerto Rico

Note: This article was posted prior to the devastating news of Hurricane Fiona on Puerto Rico.

Vacationing in San Juan? Then there’s a good chance you’re looking for things to do in Old San Juan too. The old port city has become a must-see stop in the Caribbean, featuring vibrant architecture, delicious food and a unique music scene that builds on a blend of American, European and Indigenous influences.

To that end, here’s a quick list of all our favorite things to do in Old San Juan. 

Or…you can also let your Fora Advisor do the heavy lifting and get the details from an expert who knows the area firsthand. Not to mention free upgrades, VIP treatment and more all for the same price as booking your hotel directly.

First, what’s so special about Old San Juan, Puerto Rico?

When they say “Old” San Juan, they mean old. Built in 1521, the small fortress city was among the first European settlements built in the Americas. 

Old San Juan had two purposes: one, as a trading post and, two, to defend Spain’s interests from the other European powers, pirates and the native Taíno people. Today, however, Old San Juan is the capital of Puerto Rico’s (exceptionally) thriving tourism sector. 

One of the best places to visit in Puerto Rico, Old San Juan boasts seven square blocks of gorgeous Colonial architecture, great food and tons to do.

How long do you need to visit Old San Juan? Can you walk around?

Old San Juan, Puerto Rico

You can knock out all the things to do in Old San Juan in a day or two. And yes, you can explore Old San Juan (see our guide) on foot. However, if you want to see the nearby neighborhoods too, chat with a Fora Advisor to get pro tips on travel accommodations like car rentals (and score VIP perks).

Can you visit Old San Juan at night?

Yep! Old San Juan has a heavy security presence and crime is relatively low, even at night. San Juan proper is fairly safe at night as well, though any big city carries some risk.

16 fun things to do in Old San Juan

Without further ado, here are the best things to do in San Juan.

1. Enjoy the colorful, cobblestone streets and Colonial architecture

Old San Juan, Puerto Rico's Cobblestone Streets

The first things you’ll notice about Old San Juan are its cobblestone streets and vibrant Colonial architecture. Walking tours give a glimpse into the city’s storied past and floral, beachy aromas deliver on the city’s unique charm.

Don’t forget, a Fora Advisor can provide personalized tips on the best walking (and food) tours! 

2. Stroll Fortaleza Street (aka “Umbrella Street”)

Puerto Rico Umbrella Sky Project

If there’s one street you visit in Old San Juan, let it be Fortaleza. The ramparts that line the seaside pass are a UNESCO World Heritage site and lead right past the Governor of Puerto Rico’s residence. 

You’ll also find the Umbrella Sky Project along one small section of Fortaleza. The exhibit was created to lift the spirits of locals after Hurricane Maria devastated Puerto Rico in 2017. The rainbow canopy of seemingly floating umbrellas shades the colorful street below and has become one of Old San Juan’s top places to visit in recent years.

3. Visit the Plaza de Armas

Guitar Player

There’s a pretty good chance your Puerto Rico trip planner will include Plaza de Armas on your itinerary. The plaza is arguably Old San Juan’s most popular gathering spot, hosting many of the city’s big events.

Better yet, Plaza de Armas is usually filled with live, local music and authentic food vendors so it’s a great place to sample Puerto Rican culture. In other words, many of the more lively things to do in Old San Juan can be found at the Plaza de Armas.

4. Check out the Felisa Rincón de Gautier Museum

Old San Juan, Puerto Rico

Felisa Rincón de Gautier was not only the first woman mayor in Puerto Rico; she was the first woman mayor in the United States too. Today, Rincón de Gautier is revered in Puerto Rico as being instrumental in the territory’s suffrage movement. 

Naturally, you’ll find homages to her throughout Old San Juan – chief among them, the Felisa Rincón de Gautier Museum. Here you can learn about her life and see how she lived during her tenure as Mayor of San Juan for over two decades.

5. Enjoy piña coladas in the place they were invented

pina-colada

You can’t visit the birthplace of piña coladas without trying one. Our Fora Advisor's have insider tips on Old San Juan’s cocktail scene.

You can also check out our Caribbean vacation guide for more expert recommendations on the best bar and dining options in the area.

6. See the sculpture at Rogativa Plaza

Old San Juan, Puerto Rico

If you’re searching Old San Juan for things to do, visiting the La Rogativa sculpture, housed in the plaza of the same name, boasts an interesting and rather unique story behind it. 

Just before the end of the 18th century, the British briefly attempted to invade Puerto Rico but were struggling to break through the city’s strong, seaside defenses. Two weeks on, and just as Puerto Rico’s defenders were nearing surrender, a local priest supposedly led a procession through Old San Juan, ringing bells and lighting torches along the way. 

The legend says that the British took this as a sign of incoming Puerto Rican reinforcements, and decided to withdraw rather than continue their siege.

The sculpture honors these events with large bronze sculptures and a beautiful view of the Bay of San Juan.

7. View the historic San Juan Bautista Cathedral

Old San Juan, Puerto Rico

Originally built in 1521, the San Juan Bautista Cathedral is the oldest church in the United States (and the second oldest in the Western Hemisphere). The cathedral seats the Archdiocese of Puerto Rico and offers a gorgeous demonstration of 16th and 17th-century architecture. 

And if catching the architectural sights is a top priority, a Fora Advisor knows all the best spots.

8. Buy handmade clothing, art and more at the shops in Old San Juan

woman-with-accessories

One of the more low-key (but still fun) things to do in Old San Juan is to poke through the city’s dozens of little shops and stalls, most of which feature handmade clothing, accessories and decorative pieces. Browsing the shops is an easy way to dive into Puerto Rican culture and you’ll see trinkets and accessories you won’t find anywhere else.

9. Climb the steps and walkways of Castillo de San Cristobal

Old San Juan, Puerto Rico

Castillo de San Cristobal is part of the same UNESCO World Heritage site as Fortaleza street. The castle was built in the 1600s to further solidify the Spanish’s hold on the island amid the many wars and skirmishes between European powers. 

Despite its purpose as an imposing military installation, the castle is uniquely gorgeous with a desert color palette that provides a lovely contrast with the nearby bluewater bay. Consider the castle essential viewing.

And remember, a Fora Advisor can help you immerse yourself in the local culture with pro tips and recommendations.

10. Grab a snack from a food truck on the Paseo de la Princesa

Woman On a Food Truck

If you’re looking for things to do in Puerto Rico with kids (or, you know, anyone), grabbing a snack from one or more of the dozens of food trucks should probably be near the top of the list.

In Old San Juan, you’ll find the most options along the Paseo de la Princesa, with a wide variety of sweet and savory snacks and meals.

11. Try mofongo (and other great Puerto Rican cuisine) on a food tour

Food - Plantains

Alternatively, an Old San Juan food tour is another great way to experience authentic Puerto Rican cuisine. Mofongo, a local favorite made from green plantains, garlic, pork rinds and a choice of fried (or grilled) meat, is in the must-try category but there are also plenty of alternatives for special diets.

In fact, if you prefer vegetarian or vegan dishes, a Fora Advisor can point you in the right direction. There are endless things to do in Old San Juan that involve delicious food.

12. March the steps and hills of Castillo San Felipe del Morro and walk the Paseo del Morro

Paseo Del Morro in Old San Juan, Puerto Rico

If Castillo de San Cristobal just isn’t big enough for you, then you may enjoy Puerto Rico’s most famous landmark: the Castillo San Felipe del Morro (or as the locals call it, El Morro). 

This fort is over 200 years older than Castillo Cristobal and according to the local government, has the unique distinction of being the “most successful defensive position in the New World.” The distinction bends the truth somewhat, but it is true that the castle has only been taken once (briefly).

Today, the only people laying siege to El Morro are the thousands of locals that visit every day.  

13. Take advantage of quick access to the beaches at Isla Verde

Cocktail and Beach View

Technically speaking, Isla Verde is a completely separate neighborhood from Old San Juan. However, if you’re looking for beach access, Isla Verde’s shores are walking distance from the Old Town.

Bous: Isla Verde also happens to be one of the best areas to stay in Puerto Rico. If you’re interested, speak with a Fora Advisor for free hotel tips and perks.

14. Take a sunset (or any) cruise from Old San Juan Port

Sunset Cruise

If you’re looking for a romantic getaway in Puerto Rico, it doesn’t get much better than a sunset cruise around San Juan Bay. Private charters out of Old San Juan port offer an intimate experience and unbeatable views of Puerto Rico’s natural scenery. 

Sidenote: a Fora Advisor can also help you find day trips from San Juan that hug the coast of nearby islands and beaches.

15. Check out Old San Juan’s nightlife

Don’t let Old San Juan’s family-friendly flair and Colonial architecture fool you; there are tons of things to do in Old San Juan at night. In fact, Old Town’s nightlife is booming! Every evening (and we mean every evening), you’ll find dozens of bars and streets with live music, food and dancing – especially on the weekends near the main plazas.

Our Old San Juan nightlife guide sheds more light on the late-night bar and food scene if you’re curious (and obviously, a Fora Advisor can fill you in as well).

16. See the former house of Ponce de León (aka Museo Casa Blanca)

Old San Juan, Puerto Rico

Juan Ponce de León never found the Fountain of Youth (mostly because the search is a myth) but his family’s former estate is now the site of one of Puerto Rico’s more elegant museums. 

The site collects a large variety of 16th and 17th-century artifacts along with detailed exhibits on Puerto Rico’s history under Spanish and American rule. 

Sidenote: while it may be a bummer that his alleged search for the Fountain of Youth is actually fantastical, Ponce de León is credited with the European discovery of Florida (so he’s the original Florida Man, right?).

Bonus: what’s the best place to stay in Old San Juan?

Hotel el Convento isn’t just the best place to stay in Old San Juan, it’s among the best places to stay in Puerto Rico. A prime location, storied history (the hotel was built in the 1600s) and luxurious feel will make your Puerto Rico vacation that much better.

Excited about all the things to do in Old San Juan? Let a Fora Advisor help you plan.

Eager to explore Old San Juan for things to do? Talk with a Fora Advisor and get expert travel recommendations (like the best time to visit Puerto Rico in general), free hotel perks and more – all for the same price of booking directly!

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