35 Best Things to Do in Old San Juan Walking Tour & Map

Planning a visit to San Juan, Puerto Rico? There are so many amazing things to do in Old San Juan!

This is one of my favorite Caribbean cruise ports, and you’re going to love it! I’ve visited as the embarkation point for a cruise and also for a day as a cruise port stop.

Historic San Juan is a compact area and very easy to explore on foot. So, you can see plenty of great attractions during your cruise port day in Old San Juan. And, if you’re lucky, your cruise ship will dock in Old San Juan.

I’ve got information on all the top San Juan sights right here for you (along with a handy map to point you in the right direction).

Lace up your shoes and let’s go!

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Quick Picks: Top San Juan Tours

  1. Old San Juan walking tour (Top-rated tour with local author! We took this tour on our last trip to San Juan and learned a lot.)
  2. Flavors of San Juan food tour (Award-winning tour with 4400+ 5- star reviews!)
  3. Old San Juan Segway Tour (See 25 top attractions on this small-group tour)
  4. Craft Cocktail walking tour (Old San Juan cocktail + history tour)
  5. Sunset Harbor Cruise (A romantic way to end your day in Puerto Rico!)

Table of Contents

Best Things to Do in Old San Juan Puerto Rico

1. Take a guided walking tour of Old San Juan

Colorful houses of Old San Juan, Puerto Rico in shades of lavender, ochre, mint green, and sky blue are decorated with iron balconies.  Cars line the street.
Wondering what to do in San Juan Puerto Rico? See the sights of Old San Juan on a walking tour!

Old San Juan is the perfect place to take a walking tour. Since it’s such a small area, you can certainly cover a lot of the historic city and see many incredible landmarks.

Taking a guided walking tour is a great way to get a feel for the layout of this historic city.

Plus, you’ll learn a lot more about the unique culture and history of Puerto Rico while you see some of the city’s best sights. You’ll even get tips to help you maximize the rest of your sightseeing.

You’ll find many great walking tours to choose from.

The best Old San Juan walking tour has over 2000 5-star reviews! Your guide is a local author, so you know you’ll hear plenty of amazing stories as you take in the sights. We took this tour in April and were surprised at how much ground we covered while we learned about San Juan’s history.

On this small group walking tour of Old San Juan, you’ll see top landmarks such as the Paseo de la Princesa, Calle de la Fortaleza, Castillo de San Cristóbal, and more.

See the top highlights of Old San Juan while being entertained with stories on this Old San Juan Walking Tour.

Prefer to explore on your own? That’s what we typically do!

If you’re short on time, the 11 starred items on the list below will give you a great taste of the top attractions in Viejo San Juan Puerto Rico. (And they make a convenient loop from the Old San Juan cruise port.)

2. See the Puerto Rican city crests at Plaza Dársena ***

Fountain in Plaza Darsena surrounded by mosaic city crests embedded in the plaza.  Background is a bright pink building with decorative white accents
Fountain in Plaza Dársena featuring Puerto Rico city coats of arms

If you’re arriving by cruise ship and have docked in Old San Juan, hang a left as you exit the dock and head west.  The first thing you’ll run across is the lovely Plaza Dársena, also known as Plaza de la Marina. 

This plaza overlooks San Juan Bay and has little tables and benches where you can relax and watch the ships in the harbor.

On the eastern side of the plaza is this gorgeous fountain.  The sparkling blue waters of the fountain really pop against the backdrop of this vibrant pink building (the La Casita de Rones restaurant).

Be sure to take a look at the ground around the base of the fountain. 

You’ll find several mosaic coats of arms here.  These represent different cities and villages in Puerto Rico.  You’ll also find these mosaic city crests on the northern side of the city, in Plaza San Juan Bautista.

3. Admire Art Deco architecture from Plaza de Hostos

Gray and white Art Deco Banco Popular de Puerto Rico is eight stories tall against a blue sky with clouds
Art Deco Banco Popular de Puerto Rico

One thing you’ll be quick to notice is how many plazas there are in Old San Juan, just as you would find in iconic Spanish cities such as Seville and Barcelona

Some of them are quite grand, while others are more modest.  You may find statuary, fountains, gardens, or shady benches to enjoy in a plaza.

The Plaza de Hostos is one of the more modest plazas in San Juan.  It honors famous Puerto Rican independence advocate Eugenio María de Hostos. 

Take a moment and look to the north of the plaza.  Rising eight stories is the stunning sleek building housing the Banco Popular de Puerto Rico.  This is a gorgeous building in the Art Deco style. 

Tip: Plaza de Hostos and the Banco Popular are popular tour meeting points. So this is a good place to be able to find!

4. Enjoy local cuisine on a food tour

The best way to get to know a culture is by sampling its cuisine. You’d be missing out if you didn’t try some of local Puerto Rican favorite dishes!

  • Mofongo: Mofongo is a must-try when visiting San Juan. This flavorful dish consists of mashed plantains mixed with garlic, olive oil, and chicharrones (crispy pork skin) or other fillings.

  • Tostones: Tostones are a popular dish in Puerto Rican and Caribbean cuisine. They’re made from green plantains that are sliced, fried, smashed, and then fried again until they’re crispy and golden brown.

  • Trembleque: This creamy coconut pudding, whose name translates to “trembling,” gets its moniker from its jiggly, wobbly texture. My good friend Keren (from Puerto Rico) made my family trembleque for the holidays and it was delicious!

  • Piña colada: Speaking of classic Puerto Rican drinks, we can’t forget about the piña colada. It’s one of my favorite cocktails, and it was invented right here in Puerto Rico! Enjoy some specialty cocktails on this Puerto Rico Craft Cocktail Walk.

  • Coquito: Coquito is creamy, coconut-infused drink with a hint of rum. It’s kind of like eggnog but with a distinct island twist. It’s the perfect blend of sweet, rich, and indulgent, making it a beloved holiday treat in Puerto Rico. (Keren made this for us too. Yum!)

Check out these great food tours in San Juan — your taste buds will thank you!

5.  Look at the adoquines (blue cobbles of Old San Juan) ***

Art involving adoquines (blue cobbles of Old San Juan)
Adoquines Viejo San Juan, one of the unique things in Old San Juan!

Be sure to take a look down as you are exploring Old San Juan. 

You’ll see the roads use distinctive blue cobblestones, called adoquines.  There are a few different explanations for how these blue cobbles came to Viejo San Juan.

Sources indicate that the original materials traveled to Puerto Rico as the ballast on Spanish ships.  These stones were dropped off to free up cargo space to carry precious natural resources from Puerto Rico back to Spain

The stones were then used to build various things in Puerto Rico including pavers for the roads.  Over time, the slag turned blue from exposure to the elements.

The US did a lot of renovation in Puerto Rico to bolster the idea of its Old World charm and hence to enhance its desirability as a tourist destination

This even included ordering new cobblestones to line the streets (newly manufactured to look like aged, weather-worn cobbles).

These blue cobbles are part of Old San Juan’s identity, and you can even see them as a creative foundation for San Juan’s artisan community.   (Like in the art above)

6. See the ornate San Juan Customs House

The rear of the US Customs building in Puerto Rico is pink with terra cotta designs in blue and green featuring a large eagle with a shield
US Customs House with terra cotta embellishments

The San Juan Customs House is a very ornate Spanish Colonial Revival building.  It was built in 1924 and is listed on the National Register of Historic Places. 

You can’t miss this sprawling two-story pink and white concrete building with its arched windows and doorways. 

The Customs House features terra cotta embellishments in the plateresque style, which is a Spanish architectural style featuring intricate, silversmith-like detailing.  

The terra cotta is further accented with bright colors and includes patriotic motifs such as the eagle. 

The Customs House was under renovation on our visit, so we could only get a picture of the rear of the building.  The front side, facing the harbor, is much more spectacularly decorated.

7. See the Old Arsenal of the Spanish Navy

La Antiguo Arsenal de la Armada Española translates as ‘the Old Arsenal of the Spanish Navy’. 

The thought of the Spanish Armada certainly conjures a trove of mental images featuring treasure-laden galleons, cannons, and pirates.

The Arsenal is a Neoclassic building constructed in the 1800s by the Spanish.  As you can guess, it stored weapons and ammunition.  Today, you’ll find it used to showcase cultural events and art exhibitions.

The simplicity of the Arsenal’s design is a significant difference from its fancy neighbor, the US Customs House.

8. Stroll along the Paseo de la Princesa ***

Paseo de la Princesa is a wide tree lined sidewalk in Old San Juan.  Ornate lamp posts and benches flank the walkway.
Stroll along the paved Paseo de la Princesa , one of the top places to see in Old San Juan

The Paseo de la Princesa is a wide paved sidewalk framed by trees and ornately wrought lamp posts. 

It heads due west towards the sea and the fabulous plaza containing Fuente Raíces.  There are many benches bordering the wide walkway where you can relax in the shade and engage in some people-watching.

Since it is such a photogenic location, you’ll find a lot of folks here trying to get that Insta-worthy shot.  You’ll likely need to wait your turn for a perfect Paseo de la Princesa picture.  

Note there are some public restrooms in a small building on the south side of the Paseo de la Princesa, close to its eastern end.  There were other public restrooms indicated in Google maps in Old San Juan, but these were the only ones we were actually able to locate.

9.  Relax in the Jardin del Paseo la Princesa

Fountain in Jardin del Paseo la Princesa
Fountain in Jardin del Paseo la Princesa, one of the hidden gems in Old San Juan

Most people dash west along Paseo de la Princesa to the fabulous fountain at its western end.  But if you do that, you’ll miss out on some pretty cool stuff.  

It pays to take your time and explore all the little nooks and crannies that you run across in Old San Juan.

To the north, you’ll find the Jardin del Paseo la Princesa

This lovely little garden plaza sits between the Paseo and the high fortified walls surrounding old San Juan.  This is one of my favorite hidden gems in Old San Juan.

Statue in Jardin del Paseo la Princesa features a smiling woman dressed up with a fan and pearls sitting on a stone bench.  Trees and green plants fill the background.
Intricate statues are one of the best things to see Old San Juan has to offer

The garden features lush plantings and a gorgeous fountain.  It also contains this wonderful statue of a woman all dressed up in a floral suit accented with pearls and her fan.  

10. Fuente de la Herencia de las Américas 

Continuing west from the Jardin del Paseo la Princesa, you will find Fuente de la Herencia de las Américas. 

This translates as Fountain of the Heritage of the Americas – which is a bit misleading as I couldn’t find a fountain.

Instead, you will find a small plaza with a symmetrical double staircase with bronze statues created by sculptor José Buscaglia.

11. Pop into the former prison of La Princesa

As you stroll toward the sea along Paseo de la Princesa, you’ll note a grand historic building to your right:  La Princesa.  At one time, La Princesa was a prison

Today, it houses a tourist information office and an interesting art collection.  You can stop in and get a nice map of Puerto Rico including a detailed map of Old San Juan.

The lady staffing the information desk let us know that we could view some of La Princesa’s original prison cells.   So, of course, we had to take a quick peek. 

Walk straight through the building and out the back door.  A narrow passageway on the right leads to the cells, with the fortified city walls looming large in the background.  

12. See the lovely Raices Fountain ***

Fuente Raíces features a grouping of statues rising from the fountain including a horse and several figures.  Standing at the top is a figure of a woman with arms outstretched to the cloudy sky.
The magnificent Fuente Raíces is definitely a must see in Old San Juan

Raices Fountain (Fuente Raíces) is located in a grand plaza at the westernmost end of Paseo de la Princesa.  The shimmering waters of the bay serve as a lovely backdrop to the plaza’s majestic fountain — a must see in Old San Juan!

Unveiled in May of 1992, Fuente Raíces celebrates the 500th anniversary of Spain’s ‘discovery’ of the New World. 

This is one of the most gorgeous locations in Old San Juan. So, it is understandably very popular for photos. 

From Fuente Raíces, if you look to your north, you can get a good view of La Fortaleza, the governor’s mansion.

13. Walk along the El Paseo del Morro National Recreational Trail ***

Paseo del Morro San Juan Puerto Rico.  The beige stone of the city walls rises high to the right along with a sentry box.  To the left is the blue waters of the harbor.  A palm tree is in the foreground.
Taking a walk on the Paseo del Morro Recreational Trail is one of the best free things to do in San Juan Puerto Rico

Head north from Fuente Raíces and you’ll find El Paseo del Morro National Recreational Trail

This waterside trail is one of the best activities in San Juan Puerto Rico (and one of my personal favorites!).

This paved one-mile trail is an easy walk that will take you to Paseo del Morro, the headlands underneath Castillo San Felipe del Morro, one of Old San Juan’s forts. 

This is a picturesque stroll: to your right are the imposing fortified city walls of Old San Juan, studded with garitas (sentry boxes).  And to your left, you have an expansive view of the sea with ocean waves rolling in and crashing on the rocks. 

View southwards along Paseo del Morro Recreational Trail featuring La Fortaleza in the background and the sun shining off the waters of the harbor.
View southwards along Paseo del Morro Recreational Trail featuring La Fortaleza, one of Old San Juan’s top attractions

As you reach the end of El Paseo del Morro National Recreational Trail, you can get a fantastic view looking back towards Fuente Raíces. 

The castle-like governor’s mansion, La Fortaleza, gleams in the sunshine atop the city walls.

14. Walk through the San Juan Gate ***

The San Juan Gate is a vivid brick red portal passing through the thick stone of the city walls.  The doors of the gate are sixteen feet high.
The doors of the massive San Juan Gate mark the entrance to Old Town San Juan Puerto Rico

The Puerta de San Juan, or San Juan Gate, was the main access point to Old San Juan for visiting dignitaries and travelers during Puerto Rico’s Spanish colonial era

The gate’s towering wooden doors would have been closed and barred at sundown to protect the city from invaders.

There were originally several such gates in Old San Juan, but this one is the last one remaining today. 

The massive San Juan Gate is painted a vibrant red, which really makes it stand out against the surrounding stone.  

The doorway passes through the city walls and measures sixteen feet high and twenty feet thick.  The Puerta de San Juan as you see it today was built in 1635 (with various restorations since).

If you want to pop through the San Juan Gate into Old San Juan for refreshment before continuing along the trail towards the fort, this is your opportunity.

15. Watch the cats at Parque de Los Gatos

Black and white cat sitting on a rock in San Juan's Parque de Los Gatos
Handsome cat posing in San Juan’s Parque de Los Gatos

As you walk along El Paseo del Morro National Recreational Trail, take a close look at the shrubbery lining the pathway.  Chances are, you’ll see quite a few cats dozing in the shade or stalking a bird or a lizard.

There is a large feral cat colony along El Morro Trail.  Save-a-Gato is a nonprofit organization dedicated to improving the welfare of the cats of Old San Juan. 

They work to find homes for the stray cats of Old San Juan, but cats that are feral and non-adoptable are returned to this colony.  The volunteers provide food and water for this feral cat colony to ensure their well-being.

Although most of the cats keep to themselves, this dapper fellow hopped up on a boulder and obligingly posed for our photo.

16. Enjoy the views from the Paseo del Morro viewpoint

Watching the surf is one of the best Puerto Rico things to do!

El Paseo del Morro National Recreational Trail ends at the tip of the peninsula, guarded by Castillo San Felipe del Morro looming overhead.   From here you have a decision to make. 

One option is to walk back along the trail towards the Puerta de San Juan and Fuente Raíces. 

If you’re ready for a bit more exertion, you can choose to climb the stairs to Castillo San Felipe del Morro and explore the fort.

But, before you do either of those things, take a few minutes to enjoy the views.  Watch the waves rolling in and crashing along the rocks.  I always find the sound of water relaxing!

17. Explore the historic fortress of El Morro ***

El Morro fort as seen from the sea.  The fort has tall stone walls and is topped with a lighthouse.  Waves crash against the rocks in the foreground. The background shows the colorful houses of La Perla
Castillo San Felipe del Morro as seen from the sea, with the colorful houses of La Perla– one of the best things to do in Puerto Rico!

Castillo San Felipe del Morro, commonly referred to as ‘El Morro’, is one of Puerto Rico’s historical defensive structures and impressively spans six levels. 

This citadel was constructed during the 16th through 18th centuries.   It is part of the San Juan National Historic Site, a UNESCO World Heritage Site, and is one of the top San Juan attractions. 

Across the bay from El Morro is a smaller fort, Fortín San Juan de la Cruz (called El Cañuelo).  These two forts protected the bay by setting up a deadly crossfire that would block enemy ships from being able to enter the harbor.

If you are arriving in San Juan by cruise ship, you can’t miss it as you near the island and enter the harbor.  It’s one of the best sights in Old San Juan!

Here you view the grand fortress of El Morro protecting the harbor.  In the background you can glimpse the colorful buildings of La Perla, Old San Juan’s historical shanty town. 

Visiting El Morro

After you climb up the stairs from the Paseo del Morro Trail, you’ll reach the grounds of the fort – which are actually quite extensive. 

You can explore the grounds for free, but if you want to tour the fort and visit its museum, you’ll need to pay a fee.  (Note that this ticket will also grant you entry to Old San Juan’s other major fort, Castillo San Cristóbal.)

Castillo San Felipe del Morro has played an exciting role over the centuries in protecting this Spanish port. 

El Morro’s defenses and artillery were key in defending Puerto Rico against attacks from the British, the Dutch, and the pirates of the Caribbean.

Long green lawn with broad sidewalk leading to Castillo San Felipe del Morro
Glacis leading to Castillo San Felipe del Morro, one of the best things to do Old San Juan

If you visit Castillo San Felipe del Morro from the land side, you’ll approach across this grand expanse of lawn called a glacis

While scenic, it is actually yet another of the citadel’s defensive features.  A glacis is a plain gently sloping downward from a fort which exposes attackers to the weaponry of the defenders.

Interested to know more about El Morro? Watch this brief video from the Smithsonian Channel:

El Morro is one of the top attractions in San Juan, Puerto Rico

18. View the Cementerio Santa María Magdalena de Pazzi

Cementerio Santa María Magdalena de Pazzi, with white stone memorial monuments.  The central chapel is circular with arches and is topped by a red dome.  To the left the waves of the ocean roll across the beach.
Cementerio Santa María Magdalena de Pazzi with its distinctive red-domed chapel

On the northern edge of El Morro’s glacis and just outside of its walls, you’ll find the Cementerio Santa María Magdalena de Pazzi.  This ornate cemetery overlooks the ocean and is the final resting place of many famous Puerto Ricans.

The most prominent and eye-catching feature of this cemetery is its chapel. 

Capilla del Cementerio Santa María is a circular building with arches and columns all around, topped by a red dome.  You will also find many gorgeous statues gracing the tombs.

19. Visit Casa Blanca, built for Ponce de Leon

Casa Blanca (not to be confused with the San Juan hotel of the same name) is a house that was built for Ponce de Leon.

You may remember him from your history books as a famous Spanish conquistador. But you probably don’t know that he was also the first governor of Puerto Rico.

Unfortunately, Ponce de Leon passed away before Casa Blanca was complete. Dating from the year 1521, Casa Blanca is the oldest residence in Old San Juan. And today it serves as a house museum filled with artifacts from the 16th and 17th centuries.

20. Visit a museum at the Cuartel de Ballajá

The Cuartel de Ballajá, or the Ballaja Infantry Barracks Building, was constructed from 1854-1864 to be used as housing for the Spanish soldiers and their families. 

This impressive 3-story building covers six city blocks and features a grand interior courtyard.   During WWII it served as a military hospital and then later fell into disuse. 

It now houses the Museo de las Américas, a museum featuring Latin American Art.   

The museum showcases three permanent collections:  Popular Arts in the Americas, The African Heritage, and Conquest and Colonization: Birth and Evolution of the Puerto Rican Nation.  

21. See the giant totem pole in the Quincentennial Plaza ***

El Tótem Telúrico in Plaza del Quinto Centenario is 40 feet tall.  It is made of clay with many designs with protrude from the column.  The background is a bright blue sky with little wisps of white clouds
El Tótem Telúrico is one of the unique things to see in Old San Juan!

The Plaza del Quinto Centenario (Quincentennial Plaza) is the highest point in Old San Juan. 

Built in 1992, the Plaza commemorates the 500th anniversary of Christopher Columbus’ first voyage to the New World. 

The focal point of the plaza is a 40-foot-tall totem pole, El Tótem Telúrico.  This totem is constructed of clay from across the Americas and symbolizes the origin of the New World.

From the totem you can look across the expanse of the grand Plaza and enjoy the ocean views.  There are benches scattered around the plaza if you want to give your feet a break!

Plaza del Quinto Centenario overlooking the Atlantic Ocean.  Lampposts and stair railings are painted a deep green.  The lower level of the plaza has accent designs in gray tiles
Plaza del Quinto Centenario is one of the best places to visit in Old San Juan

22. Photograph the colorful buildings of Old San Juan ***

Colorful buildings flanking the streets of Old San Juan in all the colors of the rainbow -- yellow, purple, green, red, white, and blue.  At the end of the street is Castillo San Cristobal
Colorful buildings flanking the streets are an Old San Juan must see!

Take a peek down any street in Old San Juan, and you’ll see a lovely jumble of colors and styles. 

Colorful buildings are common in the Caribbean, as bright colors help to reflect the rays of the sun and keep the interior rooms cooler.

The buildings contain hotels, restaurants, and shops all vying for your attention.  The bright, rainbow-colored buildings are accented with white-framed doorways and windows and decorative wrought iron balconies

This is definitely one of the best things to see in Old San Juan!

This view is down Calle de San Francisco.  At the street’s end, you can catch a glimpse of Castillo San Cristóbal, the largest Spanish fort in the New World.

23. See the Catedral Basilica Menor de San Juan Bautista ***

Catedral Basilica Menor de San Juan Bautista was first built on this site in 1521.  After being destroyed by a hurricane, it was rebuilt in 1540. 

It is the second-oldest cathedral in the Americas, and the oldest church on US soil.

The Cathedral is located rather close to the San Juan Gate, the primary point of entry for travelers to the city.  It is said that sailors and visitors to Puerto Rico made this church one of their first stops upon their arrival, to thank God for a safe journey.

The cathedral’s neoclassical exterior is rather plain and austere, painted mostly white with few embellishments.  But the interior is definitely worth a closer look. 

Inside, you’ll find soaring arches, brilliant stained-glass windows, and the tomb of San Juan’s founder, the famous explorer Juan Ponce de Leon.  (The Puerto Rican city of Ponce is named in his honor.)

24. Relax in Plaza de Armas ***

Four Seasons fountain in Plaza de Armas features four figures spaced around the fountain facing outward.  The background is a large white building, with a bright yellow building to the right.
Four Seasons fountain in Plaza de Armas

Plaza de Armas is the Old San Juan’s historic town square.  To its north, you’ll find city hall, and to its west, the Puerto Rico Department of State. 

The plaza features this lovely fountain anchored by four 19th century statues.  These four statues, representing each of the four seasons, were originally located on the corners of the plaza.

There are many benches lining the edge of the plaza. 

Buy a cup of coffee and a pastry from one of the nearby vendors and entertain yourself with a little people-watching.  Be careful—you might have to fight some pigeons for your snack!

25. Enjoy harbor views from the Bastión de las Palmas de San José

Old San Juan is protected by the fortified city walls, complete with garitas (sentry towers) – all part of the San Juan National Historic Site. 

As you criss-cross Old San Juan by foot, whenever you reach an ‘edge’ of the old city, you’ll get a great view. 

The Bastión de las Palmas de San José is one such locations.  It is a small plaza with benches, lots of shady trees, and fantastic harbor views. There is a garita here, although there is a door blocking public entry. 

This plaza does come with a little something extra:  two whimsical cat chair statues. 

26. Seek out the Capilla del Santo Cristo de la Salud

Capilla del Santo Cristo de la Salud .  Tiny chapel with a gate covering the arched entrance.  The rooftop including the small bell tower is completely covered with pigeons.
Tiny chapel in Old San Juan

Capilla del Santo Cristo de la Salud (Chapel of the Holy Christ of Health) is a tiny chapel on the edge of Old San Juan near the city walls. 

It was built in the 18th century in the Spanish Baroque style and sports a tiny belfry.  When we were exploring Old San Juan, we overheard a tour guide tell the origin story of this chapel. 

Story has it that a horse race occurred on Calle del Cristo. There was an accident in which one of the riders could not stop his horse and went over the cliff. 

Stories vary as to who invoked the aid of Santo Cristo de la Salud, but the young man miraculously survived the fall from the cliff. The Secretary immediately ordered the construction of this chapel to honor the miracle.

Pilgrims visit the Capilla del Santo Cristo de la Salud in hopes of benefiting from its healing powers

It is only open on certain days and times, so check before your visit if you want to view the interior of the chapel.

Next to the Capilla del Santo Cristo de la Salud you’ll find the Parque de las Palomas.  This translates to ‘Park of the Doves’ or ‘Park of the Pigeons’, and you’ll always find flocks of pigeons atop the chapel. 

27. Visit La Fortaleza

La Fortaleza, also known as Palacio de Santa Catalina, was the first of San Juan’s original fortifications and is part of Puerto Rico’s UNESCO World Heritage site

This fortress was built in the 16th century to protect Puerto Rico’s valuable harbor. 

La Fortaleza is Puerto Rico’s governor’s mansion.  This impressive structure is the oldest executive mansion to be continuously used in the New World and has housed 170 governors over the centuries.

Stories say that in 1898 as Puerto Rico was invaded by the United States, the last Spanish governor of Puerto Rico hit the longcase clock with a sword.  The clock stopped at that moment and forever marks the time at which Spain lost its control over Puerto Rico.

How to see La Fortaleza

View of Old San Juan from the harbor, featuring La Fortaleza.  Colorful buildings of San Juan sit atop the dark stone of the city walls.  La Fortaleza is a bright white building with  round crenellated towers.  The red San Juan Gate can be seen at the left edge.
Wondering what to see in old San Juan Puerto Rico? How about this fabulous view of Old San Juan from the harbor?

The portion of La Fortaleza facing the harbor looks very much like a medieval castle, complete with a large round tower and crenellations.   

The newer additions which face inland feature stately Neoclassic architecture.  You can visit La Fortaleza as part of a guided tour, but you cannot explore on your own.

You get an excellent view of La Forteleza from the harbor.  As you can see in this picture, it gleams a brilliant white in the rays of the setting sun. This makes it a vivid contrast to the stone city walls. 

Be sure to keep an eye out for La Fortaleza as you are sailing out of San Juan as you’re savoring a refreshing a delicious drink on your cruise!

28. Shop along vibrant Calle de la Fortaleza (Umbrella Street) ***

Vibrant pink butterflies are strung over the Calle de la Fortaleza, giving the buildings a pink tinge.  Buildings with wrought iron balconies line the road.
Vibrant pink butterflies at Calle de la Fortaleza, one of the most popular attractions in San Juan Puerto Rico

Calle de la Fortaleza is, literally, the road that leads to La Fortaleza.

This road boasts many restaurants, shops, and bars and bustles with activity.   Also known as ‘Umbrella Street‘, this road is popular for its colorful decorations.

 On the day of our visit, Calle de la Fortaleza was bathed in vibrant pink from the installation of hundreds of pink butterflies strung overhead. 

The overhead art on this road changes over time – sometimes it is decorated with umbrellas in all the colors of the rainbow, sometimes swathed in giant Puerto Rican flags

Calle de la Fortaleza has become a tourist attraction of its own for these colorful displays.

29. Stroll through historic Plaza Colon

White stone monument to Christoper Columbus.  Columbus stands atop a tall pedestal, with a deep blue sky in the background.
Statue of Christopher Columbus in Plaza Colon

Plaza Colon is a plaza located at what used to be the easternmost edge of Old San Juan. 

The Plaza features, not surprisingly, a monument to Christopher Columbus.  This was erected in 1893 for the 400th anniversary of the ‘discovery’ of Puerto Rico.  

Previously, the plaza featured a statue of Juan Ponce de Leon, which was relocated to Plaza San Jose.

Many restaurants and shops surround this popular plaza, often used for markets and vendors.  On its south side, the plaza is bordered by the Teatro Tapia, one of the oldest freestanding theaters in the United States. 

On its east side is the striking Antiguo Casino de Puerto Rico. And, from here you can see the imposing fortress of Castillo San Cristóbal just a stone’s throw to the northeast.

30. Explore Castillo de San Cristóbal

The imposing dark stone bastions of Castillo de San Cristóbal.  Brightly colored US and Puerto Rican flags wave in the breeze.
Explore the imposing bastions of Castillo de San Cristóbal, one of the best things to do in Puerto Rico

Castillo de San Cristóbal, or Saint Christopher’s Castle, is the third of the trio of fortresses you’ll find in Old San Juan.  

It is named after Saint Christopher, the patron saint of land travelers, and is one of the best Old San Juan tourist attractions.

 Construction on Castillo de San Cristóbal began after Puerto Rico’s existing defense system proved unable to sufficiently withstand attacks from the English and Dutch. 

The Spanish really went all-out on this citadel – it is the largest Spanish fort in the New World, covering over 27 acres.  The first shots in the Spanish-American War were fired from this San Juan fort.

Castillo de San Cristóbal is part of the San Juan National Historic site and is open to the public daily.  There is a fee for entry, but your ticket will also allow you to visit San Juan’s other major fort, El Morro. 

Definitely give yourself time to explore the citadel and its interesting defensive features – triangular bastions, sentry boxes, a deep dry moat, and an extensive network of tunnels.   

From Castillo de San Cristóbal, enjoy amazing views of the coastline and its sister fortress, El Morro.

Castillo de San Cristóbal, the largest Spanish fort in the Americas.
Visiting Castillo de San Cristóbal, the largest Spanish fort in the Americas, is one of the best Old San Juan things to do

You can really get an appreciation of the scope of Castillo de San Cristóbal from a distance – this picture is from the top deck of our cruise ship docked in Old San Juan’s harbor. 

Garita del Diablo (The Devil’s Sentry Box)

There are plenty of garitas, or sentry boxes, throughout San Juan’s forts and fortified city walls.  One of Castillo de San Cristóbal’s garitas has its own legend:  Garita del Diablo (the Devil’s Sentry Box). 

This particular garita is the most isolated and projects out further from the coast into the ocean. 

Stories say that strange noises were often heard at night here, in addition to the loud crashing of the ocean’s waves.  So, between the unusual noises and its remote location, the guards didn’t like being stationed for duty at this garita. 

At night sentries would shout to check on each other.  One night a soldier named Sanchez was on duty, but didn’t respond to any of his compatriots’ calls. 

The soldiers were afraid to check on his safety until dawn – and all they found was his weapon and uniform.  And so, the legend was born that he was taken by the devil.

The more pragmatic offer another explanation:  Sanchez ran off that night with his true love, fleeing under the cover of darkness since her family did not approve of him.  (And yes, in this version, she brought him a change of clothes!)

31. Admire the Old Casino of Puerto Rico

The grand Antiguo Casino de Puerto Rico is an elegant light gray building with white decorative embellishments.  The roof is a curved copper dome.  Tall palm trees and flagpoles in the foreground.
The grand Antiguo Casino de Puerto Rico

Just south of Castillo de San Cristóbal you’ll find the Antiguo Casino de Puerto Rico

This beautiful building was constructed in 1917 as a social club but has changed purpose many times over the decades. 

The exterior of the Old Casino of Puerto Rico calls to mind a romantic graceful age.  Tall columns flank the entryway, balconies abound, and its domed metal roof gleams copper in the sun. 

The interior is also gorgeous with white marble floors, a grand staircase, and a sparkling 12-foot-tall chandelier.

32. Tour the Capitol building

The Capitol Building in San Juan, Puerto Rico.  Many stairs lead up to the columned entrance, with the dome peeking out from the top.
The Capitol Building is one of the top Old San Juan attractions.

Puerto Rico’s Capitol, El Capitolio, is a stately Neoclassical building.  Also known as ‘The Palace of Laws’, it symbolizes Puerto Rican self-government and houses the Puerto Rican legislature.  

El Capitolio is open to the public on weekdays, so feel free to take a look around. 

Enjoy the classical architecture and décor, from the marble floors and columns to the detailed paintings on the inside of the dome portraying Puerto Rican historical events.

Cross the road to Plaza San Juan Bautista to enjoy the best views of the capitol.  This grand semicircular plaza honors Saint John the Baptist and features the mosaic city crests like the ones seen at Plaza Dársena.

33. See the magnificent mosaics

Even if you have no need of visiting the Tourist Information office, you’ll want to make a stop at this one. 

Be sure to approach from the south side of the building, on Paseo Covadonga.   The tourist information office is a charming salmon-colored building with white accents. 

But the real star of the show is the fantastic art just in front of the office. 

There is a gorgeous brightly colored mosaic that stretches over twenty feet in length. 

Mosaic art decorating stairway in Old San Juan, Puerto Rico.  Mosaic depicts an anatomical heart in red with blue veins.  The heart is pierced with a white arrow and surrounded by white flowers.  The background is bright yellow.
Mosaic art decorating stairway in Old San Juan, Puerto Rico

And just a smidge further to the west, you’ll find this spectacular staircase mosaic.  (I do love staircase art!)  The detailing on the bottom two stairs reads: “Fiestas de la Calle San Sebastian 50 anos / Los 500 anos de la Ciudad de San Juan.” 

Old San Juan has so much fantastic street art, from murals to mosaics.  This makes it such a joy to explore all the nooks and crannies of the city. 

Take your time strolling Old San Juan so that you don’t miss any hidden treasures!

34. Go for a walk in the park at Bahía Urbana

Seahorse statue at Bahia Urbana
Bahía Urbana waterfront park

Along the edge of the harbor is the Bahía Urbana

Long term, it will redevelop the waterfront area and transform it into a major tourist destination with high end shops and restaurants.  For now, it is mostly a beautification of the port area. 

If you head eastward from the Old San Juan Cruise Port Terminals, you can’t miss Bahía Urbana.  It announces itself with this large spiraling stone monument. 

There are lots of arty chairs, shade areas, and water features along Muelle 6 (dock 6) heading towards this giant seahorse statue.

There is a pedestrian bridge connecting over to Muelle 8 (dock 8) which is a large park-like area with a carousel, an outdoor dining area, and public restrooms.

35. Take a selfie with the ‘I love PR’ sign

I Love PR sign with woman in a purple shirt and hat.  Celebrity Reflection cruise ship is in the background.
I Love Puerto Rico, don’t you? Why not visit Puerto Rico?

Yes, indeed, I love Puerto Rico!  And I’m willing to bet that you will too.  This sign is located along the waterfront right by the cruise ship docks for your easy photo op.

Old San Juan Attractions Map

With so many great things to see in Old San Juan, you might be having a hard time figuring out where the attractions are located. Here is a map of these attractions in San Juan to help you get your bearings:

Old San Juan Puerto Rico Travel Tips and FAQ

When is the best time to visit Puerto Rico?

The best time to visit Puerto Rico is in the winter and spring, when the temperatures make for a great escape from cold winter climates. This is also the most popular time for Caribbean cruises to Puerto Rico.

Puerto Rico is still quite popular in the summer, when temperatures are hotter.

Do I need a passport to go to Puerto Rico?

The island of Puerto Rico is a US territory, so if you’re a US citizen, you don’t need a passport to visit!

What is the currency in Puerto Rico?

The official currency in Puerto Rico is the US Dollar.

What is the language in Puerto Rico?

Spanish is the official language of Puerto Rico, with English being the second official language. 

Do a little homework before your trip and brush up on a few common phrases in Spanish.  Easy phrases like ‘hello’, ‘please’, and ‘thank you’ go a long way in any foreign destination.

Where is Puerto Rico located?

Puerto Rico is located in the Caribbean, and it is one of the islands of the Greater Antilles.  

What is the weather in Puerto Rico?

Puerto Rico’s year-round temperatures are pretty consistent, with highs in the 80s and lows in the 70s. 

Final Thoughts:

I hope you have enjoyed this whirlwind tour of Old San Juan as much as we did! Now you know exactly what to see in Old San Juan on a cruise!

You may also enjoy these posts on my favorite winter cruise port destinations in Mexico and the Caribbean:


Are you ready to book your trip to San Juan?


Looking for the top picks for your trip to San Juan? Here are some of the best tours and hotels to help you plan the perfect vacation!

Top Tours and Experiences in San Juan:

  1. Flavors of San Juan food tour (Award-winning tour with 3300+ 5- star reviews!)
  2. Mixology class at Casa BACARDÍ (Distillery tour + cocktail-making class!)
  3. Old San Juan Segway Tour (See 25 top attractions on this small-group tour)
  4. Craft Cocktail walking tour (Old San Juan cocktail + history tour)
  5. Old San Juan walking tour (Top-rated tour with local author guide)
  6. Sunset Harbor Cruise (A romantic way to end your day in Puerto Rico!)

Top Hotels in Old San Juan:

  1. CasaBlanca Hotel (We stayed here before our cruise. Enjoy the rooftop deck with stone bathtubs overlooking the city!)
  2. Hotel El Convento (Fabulous 4-star hotel in a former convent!)
  3. Sheraton Old San Juan (Best-selling waterfront hotel with a rooftop pool!)

Planning a visit to San Juan, Puerto Rico? Pin this for later!

things to do in Old San Juan



Lisa Garrett

Lisa Garrett is the founder of Waves and Cobblestones. She has taken 35 cruises ranging from a multi-generational Caribbean cruise to solo Alaska cruises to fabulous Mediterranean cruises.

She lived in Ireland for 4 months and has taken over a dozen multi-city vacations in Europe (France, Italy, Portugal, Belgium, and more!). Lisa helps people plan amazing vacations to Europe and popular cruise destinations.

Learn more about Lisa!

Me, traveling in Venice by gondola

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