19 Incredible Things to Do in Old San Juan, Puerto Rico

Planning a trip to San Juan, Puerto Rico soon? Check out this post for some incredible things to do in Old San Juan!

From its stunning beaches to its buzzing night life, Old San Juan has it all. Whether you’re a beach bum, a foodie, or a night owl, there’s something for everyone to do in Puerto Rico’s beloved capital. Highlighted by the summer tune Despacito, Old San Juan definitely lives up to the music video’s portrayal with its colorful houses and cobblestone streets. So, if you’re planning on visiting this marvelous city for the first time, you’re in luck. This post will highlight 19 of the top things you can do, see or eat in Old San Juan.

Puerto Rico Bucket List Series

P.S. This is a post in my Puerto Rico Bucket List series. Here is the complete series:

Things to Do: 19 Incredible Things to Do in Old San Juan, Puerto Rico

Instagram: 10 Incredible Old San Juan Instagram Spots

Do a Photo Shoot (things to do in old san juan)

Doing a photoshoot in Old San Juan is a great way to spend time in the city. You can sign up for one on Airbnb if you search under Experiences and San Juan for the location. For example, for my trip to San Juan, I signed up for the Old San Juan Photoshoot & Walking Tour. In this tour, Janice will take flawless photos of you for an hour and a half by the beautiful corners of Old San Juan. Her rates right now are at $75 per person but for a private group it’s at $125. The per person rate would be best for any solo traveler but if you’re not visiting San Juan alone, I highly recommend the private group rate. So, if you’re planning on booking this experience on Airbnb, do it fast! Spots can fill up quickly so you definitely don’t want to miss out.

Explore the Colorful Streets (things to do in old san juan)

Exploring the colorful streets of Old San Juan is another great thing you can do in the city. As you walk by each building, take note of the beautiful colors that catch your eye. Many of these buildings sport different colors like lemon, pink, peach, baby blue, or mint green. In fact, if it’s helpful, you can even do a walking tour with the Tripolin Tours to get a better sense of the city. Their tour is usually ideal for first-time visitors of Old San Juan and the duration is usually around two hours. So, if you’re interested in booking a walking tour around Old San Juan, I highly recommend it. The Old San Juan Walking Tour provided by the Tripolin Tours is easy to fit in a day of sightseeing and you’ll get personalized attention within a small group.

Check out the Umbrella Sky Project (things to do in old san juan)

Checking out the Umbrella Sky Project is another great thing you can do in Old San Juan. You can find the project on Fortaleza St as you walk around the historic district. The project itself was developed by the firm Sextafeira Produgues, who is dedicated to creating various urban installations using low-cost concepts. The project began in 2011 in Águeda, Portugal and since then this colorful phenomenon later appeared in other countries like Romania, Great Britain, Germany, Spain, Korea and etc. So, if you’re planning on visiting the Umbrella Sky Project in Old San Juan for the first time, I highly recommend it. They might not be up by the time you go visit them but looking at the Tripadvisor reviews is the best way to check.

Visit the Governor’s Mansion (things to do in old san juan)

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Visiting the Governor’s Mansion is another great thing you can do in Old San Juan! Situated at the end of Fortaleza St, La Fortaleza or the governor’s mansion was originally built as a huge fortress structure to secure the island’s defenses. However, back then, it didn’t do so well. It fell under Earl of Cumberland in 1598 and it fell again under the Dutch Commander Boudewyn Hendrick in 1625. In fact, it wasn’t until 1846 that the fortress structure was remodeled and converted for full-time use as the governor’s house. So, if you’re planning on visiting the governor’s house on Fortaleza St for the first time, I highly recommend booking a guided walking tour between 8:15am and 3:30pm Monday to Friday.

Try A Pina Colada (things to do in old san juan)

Trying a pina colada in Old San Juan is another great thing you can do in the city. The drink was born right in San Juan and it was created by bartender Ramón “Monchito” Marrero at the Caribe Hilton in 1954. To concoct the drink, Ramon mixed up a fruity blend of rum, coconut and pineapple juice and he would serve it as a cocktail to his guests. In fact, it wasn’t until 1978, that the pina colada became Puerto Rico’s official drink. So, if you’re planning on trying the pina colada in San Juan for the first time, you’re in luck. San Juan has a lot of bars where you can order the famous cocktail drink. These bars include but are not limited to Barrachina, Bar La Unidad, and Jungle Bird.

Walk on the Cobblestones (things to do in old san juan)

Walking on the cobblestones in Old San Juan is another great thing you can do in the city! Called adoquines, the cobblestones in Old San Juan were blocks of ballast that were made from the waste of iron smelting. That same waste was placed on the early ships that sailed over to Puerto Rico from Spain. So, in other words, these cobblestones also tell the story of the colonial relationships Puerto Rico had with Spain and the U.S. Therefore, if you’re interested in walking along the cobblestones in Old San Juan for the first time, I highly recommend doing a walking tour. You can book some in advance on TripAdvisor so that you can learn more about Puerto Rico’s colonial history.

Visit the Sculpture at Rogativa Plaza (things to do in old san juan)

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Visiting the sculpture at Rogativa Plaza is another great thing you can do in the city. It’s a sculpture of several women, led by a priest, holding torches up high. However, the story behind the sculpture goes all the way back to 1797. Around this time, the British were planning to invade San Juan until they abandoned their attack. This was because when they thought they saw a religious procession of women walking through the streets, it was actually a reinforcement of soldiers who had arrived to help defend the city. So, if you’re planning on visiting the sculpture at Rogativa Plaza for the first time, I highly recommend it. The sculpture is near the San Juan gate and it overlooks the bay of San Juan.

Walk Inside The Historic San Juan Cathedral (things to do in old san juan)

Walking inside the historic San Juan Cathedral is another great thing you can do in the city. It’s one of the oldest cathedrals in the U.S. and it’s completely free to visit. In fact, according to Discover Puerto Rico, the cathedral is also the seat of the Archdiocese, making it a significant landmark in the city. In addition, the cathedral has also been through its own fair share of trials and tribulations. For example, in 1598, the cathedral succumbed to numerous robberies and pillaging when troops under the Earl of Cumberland sacked the city and looted the church. So, if you’re planning on visiting the Catedral de San Juan Bautista for the first time, I highly recommend it. The original building was demolished by a hurricane, but the current structure dates back to 1540.

Go Shopping (things to do in old san juan)

Shopping in Old San Juan is one of the best things you can do in the city! The area itself is known for having a ton of independent boutique shops. These shops include but are not limited to Custo Barcelona, Clubman, and Lisa Cappali. In fact, in these shops, you can also purchase the famous guayabera shirt which is a loosely-fitted patterned shirt for men in the tropics. So, if you’re a female solo traveler shopping in Old San Juan, you can get this shirt for your brother, father, guyfriend or boyfriend. However, if you don’t have a man in your life, purchase the shirt as a souvenir instead. The shops can also be located on the Cristo and Fortaleza Streets so that you can walk around and discover.

Visit Castillo de San Cristobal (things to do in old san juan)

Visiting Castillo de San Cristobal in Old San Juan is another great thing you can do in the city. Built in 1634, the Castillo de San Cristobal stands guard at the eastern gate of Old San Juan. It was created to guard the city from enemies approaching the land and it was a counterpart to Castillo San Felipe del Morro. The citadel also covers more than 27 acres and it is the largest one made by the Spaniards in the New World. So, if you’re planning on visiting Castillo de San Cristobal in Old San Juan for the first time, I highly recommend it. The fortress defended Old San Juan from many foreign attacks that included the Battle of San Juan in 1797, perpetrated by Ralph Abercromby.

Get Food at a Food Truck (things to do in old san juan)

Getting food at a food truck in Old San Juan is another great thing to do in the city. Old San Juan has plenty of food trucks located near the waterfront by Plaza Darsena and at Paseo de la Princesa too. At those trucks, you can order a lot of local puerto rican food like pinchos, alcapurillas, empanadas and tostones. Pinchos, in puerto rico, are kebabs made of grilled meat on a skewer. Acapurillas, in puerto rico, are fritters made of green bananas and taro root stuffed with ground meat. Empanadas, in puerto rico, are pastry turnovers filled with savory ingredients, and lastly, tostones, in puerto rico, are slices of unripe, green plantains that have been fried, smashed and crisped. So, if you’re planning on getting food at a food truck in Old San Juan for the first time, I highly recommend it. The dishes served are very tasty and the lemonade is great too.

Walk the Paseo del Morro (things to do in old san juan)

Walking the Paseo del Morro in Old San Juan is another great thing to do in the city! It is a boardwalk that borders the outer edge of Castillo San Felipe del Morro. On one side of the boardwalk, you’ll be flanked by the fort’s massive outer walls. On the other side of the boardwalk, you’ll be surrounded by the beautiful bay of San Juan. In fact, once you reach the doorway that gives access to the city’s walls, the Paseo del Morro will become one with the Paseo de la Princesa. So, if you’re planning on walking the Paseo del Morro in Old San Juan for the first time, I highly recommend it. You’ll get gorgeous views of the San Juan Bay and the blue sea.

Walk the Paseo de la Princesa (things to do in old san juan)

Walking the Paseo de la Princesa in Old San Juan is another great thing to do in the city! It is another boardwalk like Paseo del Morro and it starts at the historic Puerta de San Juan. On the Paseo de la Princesa, you’ll notice that it’s lined with beautifully adorned lamp posts, fountains, and street vendors. In addition, along the boardwalk, you can also find the Princess Gastrobar which is a magical restaurant where patrons can eat authentic Puerto Rican food by majestic trees. So, if you’re planning on walking the Paseo de la Princesa in Old San Juan for the first time, I highly recommend it. It’s a great place to go for a run or a walk.

Try Mofongo (things to do in old san juan)

Mofongo is another great thing you should try in Old San Juan! It’s one of Puerto Rico’s most popular dishes and it consists of green plantains, mashed with garlic and crispy pork rind. So, in other words, think of it as Puerto Rico’s version of mashed potatoes, except in this case, their version as a nice subtle sweet flavor thanks to the plantains. In addition to what I already mentioned, some locals also like to put chicken, steak, crab, shrimp, lobster or vegetables inside the mash as well. If this is the case, then the dish is usually called Mofongo Relleno. So, if you’re planning on trying mofongo in Old San Juan for the first time, I highly recommend it. In fact, some of the best mofongo can be had at El Jibarito or Café Manolin.

Listen to Some Live Music at Plaza Darsena (things to do in old san juan)

Listening to live music at Plaza Darsena is another great thing to do in Old San Juan! Located right next to Port 1, Plaza Darsena has always been the place where locals can meet with friends and listen to music. So, if you love to dance, this is your spot! In fact, usually on Sunday evenings, locals and visitors alike gather at Plaza Darsena to listen to local bands play a mix of traditional and modern music. So, if you’re planning on listening to live music at Plaza Darsena in Old San Juan for the first time, I highly recommend it. In fact, they might even play some top modern hits there like Despacito by Luis Fonsi or Gasolina by Daddy Yankee.

Go Sunbathing at Isla Verde (things to do in old san juan)

Even though Isla Verde isn’t located in Old San Juan, it’s still a great place to visit nearby. The island is a beautiful resort strip close to Old San Juan that’s lined by hotels that face one of the best beaches in San Juan, Isla Verde. In fact, Isla Verde Beach is divided into three different main beaches: Pine Grove, Alambique, and the Balneario de Carolina. Pine Grove is the beach where locals go surfing. Alambique is the beach that has a more relaxed strip of sand. The Balneario de Carolina is the beach with lifeguards and parking spaces. So, if you’re planning on visiting Isla Verde near Old San Juan for the first time, I highly recommend it. The trees there provide a lot of shade and the water is perfect for swimming.

Go Ziplining at El Yunque (things to do in old san juan)

Ziplining at El Yunque is another great thing you can do near Old San Juan. I’ve had this on my bucket list for a while now so it’s definitely on my itinerary for San Juan. In fact, the Rainforest Zipline Park in El Yunque offers many different zipline tours. These tours include the Rainforest Zipline Experience, the Rainforest Zipline Experience Plus Rock Climbing Wall, and the Adventure Trail. The Rainforest Zipline Experience tour includes eight ziplines between trees that are above the canopy level. The Rainforest Zipline Experience Plus Rock Climbing Wall tour includes the same thing in addition to a 30ft rock climbing wall. Lastly, the Adventure Trail tour includes many different activities like hanging bridges, rappelling, and hiking. So, if you’re planning on going ziplining at El Yunque for the first time, I highly recommend it. The tours at Rainforest Zipline Park are very affordable and safe.

Dance the Night Away at La Factoria (things to do in old san juan)

Dancing the night away at La Factoria is another great thing to do in Old San Juan! La Factoria is a classic bar in Old San Juan that’s known for being a vibrant hangout for socializing and dancing. In fact, if you look back at the music video for Despacito by Luis Fonsi, you’ll notice that some parts of the music video were filmed in the actual bar. In addition, through natural disasters and political turmoil, La Factoría continues to be a beacon of hope for many locals in the hospitality community and beyond. So, if you’re planning on dancing the night away at La Factoria, I highly recommend it. The cocktails there are incredible and they have some of the best hospitality on the island.

Do a Helicopter Tour (things to do in old san juan)

Doing a helicopter tour over Old San Juan is another great thing to do in the city! The Enchanted Shore HeliTour offered by Puerto Rico Helitours is a tour that will give you unrivaled views of the island as well as Puerto Rico’s natural and historical landscapes. Designed with time-pressed travelers in mind, this tour also ensures your privacy. You’ll have the helicopter tour to yourself the entire time as well as a window seat. So, if you’re planning on doing a helicopter tour over Old San Juan for the first time, I highly recommend it. Soft drinks and water are included in the tour as well as life vests and headsets.

Things to Do in Old San Juan FAQs

Here are some frequently asked questions you might have for your trip to Old San Juan!

How long do you need in Old San Juan?

I would say plan a minimum of 7-10 days in Old San Juan to get your most important areas visited with some relaxing time.

Can you walk around Old San Juan?

Yes, Old San Juan is completely walkable! The area is very compact so it’ll take you less than 45 minutes to walk to each location without stopping.

Where should you avoid in Old San Juan?

If it’s your first time in Old San Juan, you’d probably want to avoid areas like Puerta de Tierra, El Parque de las Palomas, Piñones and La Perla at night.

What is the best time of year to visit Puerto Rico?

The best time of year to visit Puerto Rico would be from mid-April to June.

Can you drink tap water in Puerto Rico?

The tap water in Puerto Rico is absolutely safe to drink in Old San Juan. Like the United States, the tap water in Puerto Rico is filtered and treated at the source.

Overall, I really hope you enjoyed this post on some of things to do in Old San Juan! Please let me know in the comments down below which thing you would like to do the most! I would love to hear from you. 🙂

P.S. If you need more Caribbean content, check out this post on the 10 Hidden Gem Caribbean Islands Not to Overlook.

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