Boulevards & Byways

7 Amazing Things to do in Old San Juan, Puerto Rico

Colorful architecture, 16th-century forts, and blue cobblestone streets. This describes the most interesting and beautiful city in the world, Old San Juan. It’s a city with a vast history and an incredible culture, which is why when you’re visiting don’t miss these 7 amazing things to do in Old San Juan Puerto Rico.

For the most up-to-date covid regulations, please visit the Discover Puerto Rico website before traveling to the island. Please note: Hours and opening schedules may have changed because of COVID-19. Please check their websites for up-to-date information.

It was 1528 when the growing and prosperous city of Old San Juan experienced its first pirate attack.  To fend off the pirates the Spanish created two huge forts and walled in the city. Today, you don’t have to worry about pirate attacks, but as a result, you’ll find yourself immersed in the history and beauty of these 16th-century forts where soldiers once fought.

1. Explore El Morro Fort

Why is it one of the 7 amazing things to do in Old San Juan?

Guarding the entrance to San Juan Bay, El Morro, a six-level fort maintained by the National Park Services, is one of the most spectacular sites in Old San Juan. It’s where stone walls meet the crashing spray of the salty Atlantic Ocean and the vast green lawn touches the azure sky dotted by kites flying in the breeze pulled by happy children at play.

It’s an immense fort built in 1539 with 18-foot thick walls, ominous dungeons, cannons pointing seaward, barracks, and mazes of tunnels. Even though it was one of the largest fortifications built by Spain in the Caribbean, El Morro suffered several attacks from the English in 1595 and 1598, and the Dutch in 1625. In 1898, during the Spanish-American War, United States Navy ships fired upon the fortification. Puerto Rico surrendered and eventually became a commonwealth of the United States, which it still is today.  During World War II, the U.S. government added an artillery fire control station.

Even if you don’t have the time or desire to visit this fort, take a stroll by it in the evening. The fort can be especially beautiful at nightfall when the setting sun illuminates the fort, casting shadows on the small, circular sentry boxes called “garitas” which have become a national symbol of Puerto Rico.

Hours: Open Daily: 9am – 5pm (June to November) and 9am – 6pm (December – May)

501 Calle Norzagaray, San Juan, 00901, Puerto Rico


Bonus: Santa Maria Magdalena de Pazzis Cemetary

Located just outside the walls of El Morro is the beautiful Santa Maria Magdalena de Pazzis Cemetery built on the coast of the Atlantic Ocean to symbolize the spirit’s journey crossing over to the afterlife. This colonial-era cemetery contains many stunning and elaborate tombstones and is the final resting place of prominent residents.

2. Visit San Cristobel Fort

Why is it one of the 7 amazing things to do in Old San Juan, Puerto Rico?

In 1634 construction began on San Cristóbal and was considered a necessary addition to San Juan’s defenses in the wake of devastating attacks from the English in 1598 and Dutch in 1625. The fortress served as a means of defense for the city of San Juan in the event of land attacks from the east.

Fort San Cristobal is thought to be the biggest fortress constructed on the American continent. With its design inspired by the 17th century Vauban-style fortresses of France, notable features of the fort include a dungeon, moat, bunker, rooms for canons, and various tunnels.  Two observation posts were added during World War II. Fort San Cristobal’s network of underground tunnels is open for exploration – the complex maze was originally utilized to facilitate easy communication and transportation of military materials, and add a level of difficulty for attackers.

At both forts, hourly tours are given by park rangers, in both English and Spanish, and provide great insight into the life of the soldiers and the history of the time. There is also a free shuttle bus that runs between them making it easy for you to see both forts in one day.

Hours: Open daily: 9 am – 5 pm (June to November) and 9 am – 6 pm (December – May)

San Juan, 00901, Puerto Rico


 3. Take a Break at Casa Corte Chocolate Bar

This cold chocolate drink was delicious.

Why is it one of the 7 amazing things to do in Old San Juan, Puerto Rico?

The first time I was in Old San Juan my eyes zeroed in on the words, Casa Corte Chocolate Bar. Like a moth to a light bulb, I plastered my face to the window to see an array of delectable chocolates on display and a long, sleek bar.

The establishment’s name upheld the true sense of the words, chocolate, and bar.  Alcoholic drinks such as chocolate mimosas and white chocolate Russians can be ordered. The menu has a traditional list of foods, but with a unique chocolate twist. Cheese plates with dark chocolate sauce, grilled cheese with cheddar and dark chocolate, their “traditional” sandwich with roasted beef, pork, turkey, Swiss cheese and a dark chocolate sauce,  and of course a variety chocolaty delicious desserts.

We sat at the bar and were immediately given small samples of hot chocolate.  Rich and creamy, it was amazing, but since it was 90 degrees out, I wanted something cool. I ordered the chocolate frio, (cold chocolate). The tall, cold glass filled with sweet liquid chocolate, a frothy tower of whipped cream, and a chunk of chocolate which was placed on top as if it were the bride and groom on a wedding cake.

Don't forget to taste their tapas.

We decided to try one of their tapas, mofongito.  Traditionally, mofongo is mashed plantains and either topped or filled with chicken, beef, pork, or seafood.  Here, they were a smaller version and filled with chocolate. Amazing, unique, innovative.  It’s definitely a one-of-a-kind place to grab a drink, meal, snack, or even chocolates to take home.

Hours: 8am-8pm

210 Calle San Francisco, San Juan, 00901, Puerto Rico


4. Ask for a Miracle at Cristo Chapel

The Chapel is open on Tuesdays.
The Chapel is open on Tuesdays.

Why is it one of the 7 amazing things to do in Old San Juan, Puerto Rico?

Cristo Chapel is hallowed ground for those who are in need of a miracle. This 16th-century gothic chapel is formally known as the Capilla del Santo Cristo de la Salud, and more commonly known as the Cristo Chapel.

As legend has it, in 1753 a rider in a horse race, Baltazar Montanez, lost control of his horse plunging to the cliffs below. The Spanish Secretary of Government, Don Mateo Pratts was watching and cried out, “Christ of Good Health, save him!” The horse didn’t survive the fall, but the young rider was miraculously saved.

That same year Montanez built the small chapel on the exact spot where he fell over the cliff – atop the ancient wall that once protected the old city. The altar was built in shining silver and gold leaf, surrounded by beautiful oil paintings by the famous Puerto Rican artist Jose Campeche.

This tiny but well-appointed chapel hasn’t changed since Montanez built it.  Over the decades believers who come to the chapel seeking miracles for physical illness have brought tiny silver ornaments, each one representing some ailing part of the body – legs, arms, heart. These small “Milagros” still decorate the walls today.

Hours: Today the church is only open on Tuesdays and religious days and is reverentially taken care of by a group of local elderly ladies; volunteers called “La Hermandad del Santo Cristo de la Salud.” Viejo San Juan

Location: the Lower end of Cristo Street

Bonus: Pigeon Park

Take a fun walk through the pigeons in Pigeon Park.

Walkthrough the gate on the right before the chapel entrance and visit Pigeon Park, a small shaded is where hundreds of pigeons roost in crevices of the stone wall. 

 5. Shop till You Drop on Cristo Street

The shops are housed in architecturally stunning buildings.

Why is it one of the 7 amazing things to do in Old San Juan, Puerto Rico?

If you like shopping check out Cristo and Fortaleza Streets for designer goods, arts & crafts, local fare, and cigars. The Cigar House has a great selection of cigar and pipe accessories and a lounge where you can enjoy your favorite smoke.

Looking for authentic Puerto Rican clothing?  For men, purchase a Guayabera on San Francisco Street, a white button-down shirt made with cotton or linen, perfect for the warm weather in the tropics. They are typical attire in the Caribbean and are part of the national costume of Puerto Rico. 

Concalma sells unique cloth purses and jewelry made by Puerto Rican designers and artists.  1% of their online sales of bags go to Siembra Tres Vidas, an organic farm in Aibonito, Puerto Rico.  If designer fashion is what you want, take a stroll on Cristo Street where you’ll find shops such as Coach and Ralph Lauren.

Local shops in Old San Juan:

The Handcraft Store

101 Fortaleza Street, (787) 724-1181

Puerto Rican Arts and Crafts

Calle Fortaleza 204, (787) 725-5596

The Cigar House

Calle Fortaleza 257, (787) 723-5223


Unique handmade bags

Calle San Francisco 207, (787) 342-9757

House Guayaberas

Traditional white linen shirts and dresses.

Calle Tanca 202 – near San Francisco and Fortaleza Street – la Plaza La Barandilla, 787-664-4367

6. Stroll on the Paseo La Princessa

Why is it one of the 7 amazing things to do in Old San Juan, Puerto Rico?

Paseo La Princessa is a tree-lined promenade built in 1853 which follows the beautiful views of the San Juan Bay and the historic base of the city walls.  The ‘Paseo’ used to be where the local aristocrats would come to display their wealth and socialize. Here are a few things you’ll find along your walk on Paseo La Princesa along with a self-guided walking tour. 

On the weekends, vendors set up booths containing various foods as well as arts and crafts.  It’s a great place to pick up a snack or a trinket to commemorate your visit.

A former jail is now home to the Puerto Rico Tourism Company.  Here you can get tourist information, grab a map of Old San Juan, (which I highly recommend), visit their art gallery, walk around the elegant courtyard, and see a 19th-century jail cell.

On a hot day, the fountain will give you a cooling spray.

Raíces Fountain, also known as the Roots Fountain is considered to be one of the most romantic spots in Old San Juan, particularly when the setting sun casts its shades of copper and gold across the water in the bay outlining the dramatic silhouette of the bronze statues. This collection, honoring Puerto Rico’s mixed African, Spanish and Taino/Amerindian heritage, is represented as a ship being steered out into the open sea with leaping dolphins leading the way to a bright 21st-century future. The picturesque San Juan Bay serves as a backdrop to the statue.

As you walk further down Paseo de la Princesa you will come upon a large, red gate built in approximately 1635.  This is the last remaining gate that was built into the massive defensive walls to protect the city was the main entry into the walled city during its Spanish colonial era. The gate is closed at night.

The blue cobblestone streets and colorful architecture make this one of the most beautiful cities in the world.
The blue cobblestone streets and colorful architecture make this one of the most beautiful cities in the world.

Walk through the gate and view the blue cobblestones which line the streets and wander leisurely admiring the charming 16th and 17th-century Spanish colonial homes encompassing bright colors and interesting architecture. The blue cobblestones are adoquine, cast from furnace slag which was brought over as ballast on Spanish ships. Time and moisture have given them their blue color.

Location: 101 Paseo De La Princesa, San Juan, Puerto Rico 00901

7. Dance the Night Away

Make sure you take a salsa lesson.
Make sure you take a salsa lesson.

Why is it one of the 7 amazing things to do in Old San Juan, Puerto Rico?

Locals and tourists together can enjoy the spirited beat of salsa music at Nuyorican Café.  A talented live band, a cover charge of only $5, and a centrally located establishment make this a popular spot to dance. Don’t let its side alley entrance scare you.  At 9 pm when they open, they’ll be someone handing out flyers at the door, otherwise, you’d never know it’s there.  Salsa lessons are available at 9 pm on Wednesdays and the band generally starts at 10:15.

Address: 312 Calle San Francisco, San Juan, 00901, Puerto Rico (Even though the address is Calle San Francisco the front entrance is actually on the side street of  Calle de la Capilla.)

Where to stay in Old San Juan:

Hotel El Convento

The Hotel El Convento is in the heart of Old San Juan and is a former Carmelite convent which dates back to 1651 and is now a romantic retreat with 58 well-decorated rooms.  It’s also reportedly home to the ghosts of its nuns who haunt its halls.

Hotel Amenities include a fitness facility, bar/lounge, conference space, porter/bellhop, multilingual staff, ATM/banking, outdoor pool, free Wi-Fi, snack bar/deli, laundry facilities, refrigerator, cribs/infant beds (complimentary) and rooftop lounge area.

High-end price

100 Calle del Cristo, San Juan, 00901, Puerto Rico


Hotel Plaza De Armas Old San Juan

Overlooking the Plaza de Armas, this Spanish Colonial style 4 floor, 51 room hotel is a 9 minutes’ walk from Castillo San Cristóbal fort. Featuring wood furnishings, the low-key rooms offer flat-screen TVs with premium channels. Some rooms have no windows. Amenities include an elevator, free Wi-Fi, air conditioning, an informal coffee shop, and a sitting/dining area in a bright atrium.

Economy Price

202 Calle San José, San Juan, 00901, Puerto Rico

+1- 787-722-9191

La Terraza De San Juan

Located in San Juan Antiguo, this hotel is within a 5-minute walk from Castillo de San Cristobal fort and San Juan Gate.  All 24 individually decorated rooms feature free Wi-Fi and minibars. For a bit of entertainment, guests will find flat-screen TVs with satellite channels, and other amenities include refrigerators and premium bedding. Along with an outdoor rooftop pool, this smoke-free hotel has 3 bars/lounges and a poolside bar. Other amenities include a coffee shop/café and coffee/tea in a common area.


262 Calle Sol, San Juan, 00901, Puerto Rico


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6 thoughts on “7 Amazing Things to do in Old San Juan, Puerto Rico

  1. Erica

    I feel so fortunate to have crossed many of these things off my list and to be able to do the rest soon! I love PR and am proud to call it my adopted home!

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