Best Things To Do When in Old San Juan, Puerto Rico
Written By: Global Grit and Glam
April 2025
The Streets of Old San Juan are lined with colorful buildings
There’s something pretty magical about visiting San Juan, Puerto Rico. Perhaps it’s the mix of gray cobblestone streets, colonial charm, and that oft-welcome salty sea breeze making its way in from the Atlantic Ocean. Or perhaps it’s the undeniable sense that here, in Puerto Rico’s capital, around every corner you’ll find a story just waiting to be told.
Indeed, if you find yourself in San Juan – either as part of a day-long stop on a cruise itinerary or if you’re here for a day or two – spending some time exploring the colorful and spirited capital city of Puerto Rico is a must. What you really cannot miss, however, is the historic part of the capital – Old San Juan. Much of Old San Juan – El Viejo San Juan in Spanish – is a UNESCO World Heritage Site, boasting an incredible mix of rich history, unique culture, and a vibrant atmosphere.
Walk the narrow cobblestone streets lined with beautifully preserved colonial architecture and historic hotels, and discover lively plazas and iconic landmarks around almost every corner. For those of you seeking a glimpse into Puerto Rico’s heritage, it is here within the old world charm of Old San Juan that you’ll be afforded this very enchanting opportunity.
We provide for you here, dear fellow travelers, more than simply a list of “Old San Juan Things To Do”. What we’ve curated for you is a journey through one of the most beguiling and storied cities in the Caribbean islands.
So let’s strap on those sturdy walking shoes and get to it!
Quick Tips
Narrow cobblestone streets (Old San Juan, Puerto Rico)
Here are some insider tips to help you make the most of your visit to Old San Juan, Puerto Rico.
Getting around Old San Juan is easy – most visitors opt to simply explore on foot.
During your time in Old San Juan, take a stroll down Calle de la Fortaleza, famous for its umbrella canopy.
Visit Plaza de Armas, the first central square in the city of San Juan.
Swing by Catedral Basilica Menor de San Juan Bautista, where you’ll find the tomb of Juan Ponce de León, Spanish explorer and the first governor of Puerto Rico.
Take a peek inside the small but beautiful Iglesia de San José, the second oldest church in the Americas.
Are you into museums? Spend an hour or two at the Museo de las Américas, an institution that helps to bring to life the stories of Puerto Rico and its people.
No visit to Old San Juan is complete without a stop at Castillo San Felipe del Morro, a UNESCO World Heritage site.
Another UNESCO World Heritage site within the walls of Old San Juan is Castillo San Cristóbal, a fortress originally built in 1634 to guard the land entry to Old San Juan.
For some excellent people-watching and photographic opportunities, enjoy a stroll down Paseo de la Princesa – Promenade of the Princess.
Follow these tips and you’ll be ready to visit Old San Juan, Puerto Rico!
Plan Your Trip
View from Castillo San Cristóbal toward El Morro (Old San Juan)
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Getting Around Old San Juan
Traffic can get congested in Old San Juan: we recommend walking!
Compact in size at just over 1 square mile (2.6 square kilometers), Old San Juan is easily walkable. For those of you embarking on, or disembarking from, a cruise in San Juan, it’s likely your cruise ship will dock right at the perimeter of this historic part of town.
Insider tip. Walk with caution during your time in Old San Juan. The old part of the capital is lined with uneven and often slippery cobblestones, an important note for those with accessibility needs and also a reminder to wear comfortable shoes as you explore this wonderful 16th-century city.
Taxis and Uber are other excellent options for getting around Old San Juan, though truly not necessary. In fact, the narrow streets of Old San Juan can get easily clogged with traffic at any time of the day and we wouldn’t recommend trying to utilize the services of a taxi or Uber within the Old City Walls.
Insider tip. Due to congested traffic, if you’re looking to head out from Old San Juan to another part of the city, including the airport, we recommend walking to just outside the Old San Juan limits and hailing a taxi or Uber from there. We found Av. Luis Muñoz Rivera at Plaza Colón an excellent place for Uber drivers to easily find and pick us up without any bottleneck traffic in the way.
If you’re not up for walking, or would prefer to try something a little different, you can also rent bikes in Old San Juan. If you’d like to get the most out of your bicycle rental, consider joining a group tour to learn from a local, professional guide more about the things you’ll see along the way.
Exploring Old San Juan: A Step Back in Time
Old San Juan’s old-world charm (Puerto Rico)
The Old San Juan district is home to numerous famous historical buildings, including castles, museums, and churches. Visitors to Old San Juan can also partake in some solid retail therapy, and enjoy the delicious Puerto Rican cuisine served by restaurants throughout the area.
Let’s take you on a guided tour of some of the must-see attractions within Old San Juan.
Fortaleza Street (Calle de la Fortaleza)
The famous Calle de la Fortaleza is a must-visit
Consider starting your time in Old San Juan on Fortaleza Street (Calle de la Fortaleza), an historic street often considered one of the oldest and most photogenic streets in the city. You’ve probably seen photos of it or heard about it from other travellers … so why not take a stroll down it?
Starting at Plaza Colón in the east and running southwest all the way down toward the waterfront, Calle de la Fortaleza is home to famous colorful canopies (including the most well-recognized: umbrellas) and the official residence and seat of the governor of Puerto Rico (La Fortaleza, also known as the Palace of Santa Catalina) – a 16th-century mansion and one of the oldest buildings in continuous use within the United States and its territories.
View down Calle de la Fortaleza toward La Fortaleza (Old San Juan)
Calle de la Fortaleza is lined with a mix of governmental buildings, small galleries, boutique shops (it’s fabulous for souvenirs – Beck purchased the most wonderful handmade soaps from one of the stores here!), hotels, cafes and restaurants. Though it’s easy enough to wander this beautiful cobblestone street on your own, guided tours of Calle de la Fortaleza are available (either on foot or by Segway), providing additional insight into the history of the area.
Plaza de Armas
Once you’ve wandered along Calle de la Fortaleza, head over to the parallel street, Calle de San Francisco, for a quick visit to Plaza de Armas (formerly known as Plaza Mayor de San Juan).
Founded in 1521, Plaza de Armas was the first central square in the city of San Juan, and for the first 300+ years it served primarily as a market. Lining the plaza today you’ll find the San Juan City Hall (the center of the city’s municipal government), as well as other government buildings and large department stores. The four marble statues at the plaza’s corners today symbolize the four seasons: Summer, Spring, Winter and Fall.
Street food vendors in Old San Juan (Puerto Rico)
Spanish troops once practised military exercises in this square (hence its name!), but today you’ll often find wonderful examples of Puerto Rican culture in this main square, including street vendors, local artisans, and performers. Take a seat at one of the cafes, sip some coffee (or any other beverage) and enjoy some peaceful people-watching.
Catedral Basilica Menor de San Juan Bautista
Just a 2-minute walk from the northwest corner of Plaza de Armas you’ll find the Catedral Basilica Menor de San Juan Bautista (the Cathedral of St John the Baptist, or simply, the San Juan Cathedral) – the oldest church in the United States and the second-oldest existing cathedral in all the Americas. Construction began in 1535 (and was finally completed in 1802), and today this Catholic cathedral is a significant historical site in San Juan, complete with unique medieval architecture, marble altars, serene chapels, and the final resting place of Juan Ponce de León, Spanish explorer and Puerto Rico’s first governor.
The Catedral de San Juan Bautista is generally open daily from 8am to 6pm, with extended hours on weekends (through 7pm). There is no admission fee to enter the cathedral, but donations to help with the cathedral’s upkeep are strongly encouraged (and are often requested at the entrance). Visitors are also welcome to attend any of the open masses, held every day (including weekdays) at 12.15pm.
On the way to Catedral Basilica Menor de San Juan Bautista (Old San Juan)
Iglesia de San José
Four minutes north of Catedral Basilica Menor de San Juan Bautista by foot you’ll come across Iglesia de San José (San José Church), another significant historical landmark within the walls of Old San Juan. Constructed between 1528 and 1735, Iglesia de San José was one of the first stone buildings built in Puerto Rico, and is today listed as the second oldest church in the Americas. In 2013 it became one of the “most endangered historic places of the year” – and today remains one of the earliest surviving examples of 16th-century Spanish Gothic architecture in the Western Hemisphere. It’s definitely worth a peek inside this simple, but beautiful, church!
Whilst time – and indeed weather, war and other natural disasters – have taken its toll on the church, it was closed for renovations in 2000, finally reopening to the public in early 2021 (yes, over 20 years later!). Several notable people have been buried in the church’s crypt, including the first governor of Puerto Rico, Juan Ponce de León (though his remains have since been moved to the Cathedral of St John the Baptist). Several members of his family remain buried at the Iglesia de San José and the Ponce de León family coat of arms can be found inside the church, beside the main altar.
Iglesia de San José is a working parish and is open to visitors from Wednesday through Saturday (9am to 3pm, when mass is not in session). There is no entry fee to visit the church, though a small donation is always appreciated.
Fun fact. There are mermaids hidden within the artwork inside the church. Can you find them?
Museo de las Américas
Next up on your exploration of Old San Juan, and less than a 3-minute walk (about 200m) from Iglesia de San José, you’ll find the Museo de las Américas. Housed in the former Ballaja Barracks, a visit to this multidisciplinary, multicultural museum, founded in 1992, is an excellent way to learn more about the broader history of arts, architecture and folklore in the greater Americas.
The museum offers permanent as well as temporary exhibits that help bring to life the stories of Puerto Rico, and is dedicated – in part – to preserving and perpetuating Puerto Rican arts culture, both on the island and abroad. It also offers various educational and cultural programs to locals and visitors alike.
Castillo San Felipe del Morro
View through the towering walls of El Morro (Old San Juan)
Following a brief stop at the Museo de las Américas, you’ll soon find yourself at the entrance to the massive fort and expansive, grassy grounds of Castillo San Felipe del Morro: the crown jewel of this walled city.
Lovingly nicknamed “El Morro” (with an English translation to Promontory Castle of Saint Philip), Castillo San Felipe del Morro is a historically significant 16th-century citadel: a towering symbol of strength and endurance that lies on the northernmost point of the Old San Juan islet.
Perhaps the most iconic fortress built by Spanish colonists in the Americas – and named in honor of King Philip II of Spain – El Morro covers a 140-foot-high (43-meter) steep, rocky headland at the entrance to the Bay of San Juan. With 18-25-foot (5.5-7.6m) thick walls, it consists of six different levels, and visitors can climb the highest watchtower for panoramic views over the Atlantic Ocean, San Juan Bay and the city of San Juan.
Completed in 1790 after almost 200 years of construction work, El Morro soon became the most feared of all Spanish colonial defensive military fortifications – and indeed a major component of San Juan’s harbor defence system. It wasn’t until over 100 years later, during the Spanish-American War, when the once impenetrable El Morro took its first sizable hit. Fast forward to 1961, when the fort was “retired” and became a part of the National Park Service to be preserved as a museum, before gaining UNESCO World Heritage status in 1983.
Kite-flying is a popular activity on the expansive grounds of El Morro
Despite its historical significance, El Morro is today perhaps most famed for its stunning, sweeping green grounds, used by locals and visitors alike for picnics, flying kites, ball games, weddings and other events. If you need a moment to rest from all the walking you’ll no doubt do in and around Old San Juan during your day in port, consider stopping here for an hour or so.
El Morro is open daily (except for Thanksgiving, Christmas and New Year’s Day) from 9am to 5pm. Admission is US$10 for visitors aged 16 and older (free for everyone else), and permits entrance to both El Morro and Castillo San Cristóbal (so long as you visit within the same 24 hours).
Insider tip. The National Park Service offers free admission to El Morro on certain days of the year, including National Park Week (usually in April), Martin Luther King, Jr. Day and Veterans Day.
Fun fact. El Morro served as an active U.S. military base during both World War I and II.
Fun fact. There are reported to be over 2 million visitors to El Morro each year, making it one of Puerto Rico’s leading tourist attractions.
Fun fact. Several Hollywood films have been shot in and around El Morro, including scenes from Steven Spielberg’s 1997 historical drama Amistad.
Fun fact (yes, another one!). El Morro is home to a resident colony of close to 200 stray cats, believed to be descendants of felines introduced during colonial times as part of rat eradication programs.
Castillo San Cristóbal
A peek inside Castillo San Cristóbal (Old San Juan)
Consider finishing your walking tour of Old San Juan at the must-visit UNESCO World Heritage Site of the imposing Castillo San Cristóbal (in English: Saint Christopher Castle), a decent 20- to 25-minute walk east of El Morro along Calle Norzagaray (but only 7 minutes on foot from the Old San Juan Terminal, if you want to begin your day here).
Whilst El Morro was built to protect the city from sea-based attacks, Castillo San Cristóbal guarded the old city walls from land invasions. A giant fortress originally built in 1634, it was first called Garita del Diablo – “devil’s sentry box” – and served as an artillery platform. Over the next 150 years it expanded into a bastion fort, reaching its largest size in 1790. Today, the fortress is one of the largest forts in the Western Hemisphere - and the largest ever built by the Spanish in the New World. The fort is worth a visit for its historical significance, as well as its stunning views over the San Juan harbor.
Spanning three different levels, the most impressive features of Castillo San Cristóbal include an extensive system of underground tunnels, real mortar bombs, five large cisterns (originally used for water storage and then utilized as bomb shelters during World War II), dungeon drawings, a guardhouse and parade ground, as well as various exhibits. There is also a small souvenir shop on site and your entry fee includes a short documentary (in English and Spanish) on the city of San Juan and the castle itself.
Overlooking the Atlantic Ocean from Castillo San Cristóbal (Old San Juan)
Castillo San Cristóbal is open daily from 9am to 5pm (closed on some major holidays). The entry fee of US$10 for individuals aged 16 and above (those under the age of 16 can enter for free) can be paid at the ticket desk inside the fort – note that cash is not accepted. Make sure to hold on to your entry ticket, as it’s valid for both Castillo San Cristóbal and Castillo San Felipe del Morro, so long as you visit on the same day. Guided tours are also available.
Insider tip. If you’re in San Juan on the third Sunday of the month, you’ll be treated to demonstrations of ancient weapons firing at the castle.
Insider tip. Castillo San Cristóbal covers an area of a whopping 27 acres. Be prepared for lots of walking, as well as some stairs … and make sure to bring water with you, as it can get very hot in the middle of the day!
Fun fact. Castillo San Cristóbal was designed to catch and retain as much rain water as possible. The five underground water cisterns could hold enough water to last troops an entire year.
Fun fact. Saint Christopher is the patron saint of travelers. This feels reason enough to visit a castle built in his name!
Castillo San Cristóbal, along with Castillo San Felipe del Morro, make up a significant part of the San Juan National Historic Site.
Paseo de la Princesa
Fuente Raices, Paseo de la Princesa (Old San Juan)
If you have time – either before you head to Calle de la Fortaleza or after your visit to Castillo San Cristóbal – consider taking a leisurely stroll along the partially waterside 19th-century pedestrian-only Paseo de la Princesa (Promenade of the Princess or Princess Promenade). Just west of the San Juan Cruise Port, and less than a kilometer (half a mile) in length, it’s here you’ll have the opportunity to take in the beautiful views of the San Juan Bay and will often be treated to a long line of local artisan market stalls (especially when cruise ships are in!).
Constructed in the mid 1800s in honor of Queen Isabella II of Spain’s first-born daughter, Paseo de la Princesa is a wonderful place to buy local handicrafts and jewelry, enjoy traditional Puerto Rican cuisine from street vendors, sit on a park bench and enjoy some shade under the overhanging trees, admire the historic Victorian lamp posts, take in the myriad fountains and sculptures, applaud musical and theatrical entertainers you’ll encounter along the way, enjoy temporary art exhibitions, and soak up even more of the old-world charm that is Old San Juan. Paseo de la Princesa is also home to live jazz on Fridays and Saturdays, and on the weekends you can be treated to salsa music and dancing.
As the walled city towers above you and the sound of the ocean waves accompany your every step, the promenade also passes by numerous San Juan cultural and historical landmarks, including the following:
Old La Princesa Prison (Antigua Prisión La Princesa, dating back to 1837 – now the headquarters for the Puerto Rico Tourism Company)
the popular Roots Fountain (Fuente Raices, a large sculpture fountain in the middle of a large plaza overlooking San Juan Bay, about halfway along the promenade – whilst you’re in the plaza, also look out for the small wooden dock that offers superb views over the bay and El Yunque)
the iconic and beautifully-preserved San Juan Gate (Puerta de San Juan, formerly known as Puerta de Agua (water gate) – the old gate where dignitaries once entered the city from their arriving vessels)
La Fortaleza (the 16th-century executive residence of the governor of Puerto Rico)
the Americas Heritage Fountain (Herencia de la Americas)
the historic bastion of San Justo and Pastor (dating back to the colonial era and offering visitors a glimpse into the military architecture of the time)
One of the many monuments along Paseo de la Princesa (Old San Juan)
Paseo de la Princesa becomes the Paseo del Morro (Morro Promenade), which hugs the waterfront beneath the remainder of the western portion of the Old San Juan defensive walls.
Although the promenade (and the surrounding areas) fell into disrepair during the 20th century, it was restored in the late 1980s, and today Paseo de la Princesa is often described as one of the most scenic city walks in the world (nope, not just in the Caribbean!). For many disembarking from a cruise in Puerto Rico, the promenade is often the starting or ending point for sightseeing in Old San Juan.
Fun fact. Over the years, several time capsules have been buried beneath the promenade in front of the Old La Princesa Prison. The two remaining time capsules in this location are scheduled to be opened in 2045.
A Taste of Puerto Rico
After all that walking through Old San Juan, you’re bound to have worked up an appetite! And indeed, a visit here would not be complete without sampling some local Puerto Rican flavors.
Stop by one of the many street vendors and grab a freshly-made piña colada or fresh-pressed sugarcane juice. One of the best places to find street vendors and food trucks in Old San Juan is in the lively Plaza Colón, at the east end of Calle de la Fortaleza. If you’d prefer a sit-down meal, there are countless cafes and restaurants spread throughout the colorful streets of the old town, many using fresh, locally-sourced ingredients.
Fun fact. Piña coladas were invented in San Juan!
San Sebastián Street Festival (Fiestas de la Calle San Sebastián)
Calle San Sebastián (Old San Juan, Puerto Rico)
Do you love a good street party? If you find yourself in Old San Juan in late January, consider joining in the festivities associated with the ever-popular San Sebastián Street Festival.
The San Sebastián Street Festival – also known as “SanSe” – is Puerto Rico’s largest and most popular festival, celebrated in Old San Juan each year during the third weekend in January. Centered around San Sebastian Street and attracting over 200,000 people annually, this vibrant celebration began in the 1950s as a religious celebration in honor of Saint Sebastian. Today, this festival marks the unofficial end of the holiday season.
SanSe is an enormous cultural event and features live music and other performances, impromptu dancing, artisan handicrafts, pop-up shops, the parade of cabezudos (colorful, oversized headed figures, often made of papier-mâché), and traditional foods. SanSe represents everything that is the Puerto Rican identity: resilience, cultural pride, and unity. It is a time for Puerto Ricans to come together and celebrate their heritage.
Insider tip. During SanSe, special public transportation schedules for the bus, train and ferries are in effect to accommodate attendees who are drawn from all corners of the island.
Fun fact. As the population of Puerto Ricans living in the United States has increased, SanSe is now also celebrated in cities across Florida and Texas.
Final Thoughts
Flags fly proudly above the towers of Castillo San Cristóbal
There’s a reason Old San Juan remains one of the most beloved cities in the Caribbean. This historic city is more than just a pretty postcard (though if you’re like Beck, do make sure to buy some postcards and send them home to loved ones!) – it’s a living, breathing cultural experience, seamlessly fusing past and present.
With its colorful streets, centuries-old architecture, UNESCO World Heritage Sites, and its dramatic city walls that will envelop you in its old-world charm, make sure you take some time to explore all that Old San Juan has to offer during your time in Puerto Rico. It is, without question, a haven for history-lovers and affords visitors the opportunity to literally step back into the 16th century.
Easy to explore on foot, Old San Juan offers a variety of authentic Puerto Rican experiences for all types of travellers: strolling the historic streets, chowing down on delicious Puerto Rican cuisine, shopping for unique souvenirs, climbing atop old military forts, or simply sitting on a park bench along a picturesque promenade and taking in the world around you. This might be your first visit here, but we are confident it won’t be your last.
Are you ready to step back in time and experience the true heartbeat of Puerto Rico? Let’s start planning your trip to Old San Juan!
