Boulevards & Byways

Self Guided Walking Tour of Old San Juan

Slip-on comfortable shoes. This walking tour immerses visitors in the history, culture, and natural beauty of Old San Juan. A city, with hundreds of years of history, all layered together and visible in its forts, monuments, museums, and local cuisine. This self-guided walking tour of Old San Juan will help you hit all the main sites and areas in just a few hours.

I’ve included links to Google Maps to help you along your journey.

Welcome to Old San Juan

Calle Marina

This tour begins at Calle Marina which is where the cruise ships dock. It’s close to a reasonably priced parking garage on PR38, should you be driving into the city.

Plaza Darsenas

From the marina head west, the water will be on your left, to Calle Comercio toward Plaza Darsenas.

Casita de Rones Bar

Here you’ll see the Casita de Rones bar. It serves as a promotion center for the rums of Puerto Rico. Make a stop and grab a refreshing rum cocktail or a bite to eat.

Plaza de Hostos

Continue walking towards Plaza de Hostos. A bust of Eugenio María de Hostos stands proudly. Hostos was an avid supporter of the independence movement for Puerto Rico and Cuba. He dedicated his life to educational causes and advocating women’s rights to higher education.

What are the blue stones?

You may have noticed you’ve been walking on blue stones. Brought over on Spanish ships, they are adoquin, cast from furnace slag, and used as ballast on the ships. The characteristic blue color comes from age and moisture.

El Paseo de la Princesa

Meander toward San Juan’s most beautiful promenade, El Paseo de la Princesa. On weekends, vendors sell local art, handmade jewelry, fried treats, and piragua, a shaved-ice made with tropical fruit syrup.

Originally created in 1853, the Paseo, features a broad brick walkway. It leads visitors through a pleasant tree-lined sculptural and garden showcase.

Puerto Rico Tourism Company

The Puerto Rico Tourism Company will be on your right. This building served as the prison from 1837 to 1960. Visit the original jail cells located in the back courtyard.

Raices Fountain

The lovely views of San Juan Bay come into focus along with Raíces or Roots Fountain. The fountain celebrates Puerto Rico’s rich cultural diversity and historical heritage with Amerindian, African, and Spanish peoples represented. Sculpted by Spanish artist, Luis Sanguin.

Bacardi Factory

Looking across the bay you’ll see a few wind turbines spinning. That’s the Bacardi Rum Factory where you can embark on a tour. 

To visit the Bacardi Factory from Old San Juan, ride the La Lancha Ferry on Pier 2 to Catano. Continue to the Bacardi Factory by taxi.

Crecimiento Sculptures

Follow the walkway as it bears to the right. A collection of bronze sculptures sit along the outside of the city walls called ‘Crecimiento.’ These are the creation of Carmen Inés Blondet in 1996. The sculptures represent the affirmation of life.

The shapes, rising from the ground, convey the idea that the fragility of growth is only an impression and what is truly important has to be eternal.

Queen Isabella Sculpture

Continue following the pathway and view the sculpture of Queen Isabella in a courtyard shaded by a stately ficus tree.

La Puerta de San Juan

An immense red gate or La Puerta de San Juan, built between 1634 and 1638 turned the city of San Juan into an impregnable fortress with its 15 feet thick walls.

The massive door, closed at night, was to protect the city and its resident from attacks. Out of the three that were built, this is the only one that stands to this day.

A blessing, at the top of the gate, to all visitors as they pass through: “Blessed is he who comes in the name of the Lord.”

Caleta San Juan

Continue straight to Caleta San Juan. The colors and architecture of these 400-year old homes, the beautiful Moorish title, and hidden courtyards make this my favorite street.

Cathedral de San Juan Bautista

At the top of the street, is the graceful Cathedral de San Juan Bautista or the Cathedral of Saint John the Baptist.

The waxed-coated, mummified remains of Saint Pius (San Pio), a soldier and Christian martyr can be seen.
Visitors can view the tomb of Ponce de Leon,

Ponce de Leon, the first governor of Puerto Rico was a Spanish conquistador. He led a European expedition for gold, traveled to the southeast coast of the United States, and explored a small island to be later named, Puerto Rico.

El Convento Hotel

El Convento Hotel is on the diagonal corner of the cathedral.

Stop inside to the view of the beautiful architecture or get a bite to eat at the restaurant.

There have been numerous sightings of ghosts in the guest rooms over the years at El Convento Hotel. A Carmelite convent in the past, the popular ghost story revolves about Doña Ana de Lansos y Menéndez de Valdez, the founder.

Doña Ana was its first mother superior, and many say she never left. She and her nuns walk the halls, it has been reported. The swishing sound of their robes echoes through this hotel, even centuries after Doña Ana’s death.

El Bate bar

Head up the hill to Cristo Street or Calle de Cristo. If you’re thirsty, stop into El Bate, a little gem, with graffiti-covered walls and business cards hanging from the ceiling. Reasonably priced drinks it’s a welcome respite from the heat.

San Jose Church

Continue up Calle Cristo and on the right is the oldest church in San Juan, the San Jose Church.

Built in 1532, it is one of the finest and oldest examples of Gothic influenced architecture built by the Spanish in the New World. Currently under renovation, it is closed to visitors.

Institute of Puerto Rican Culture

As the road bears to the left, the Institute of Puerto Rican Culture will be on the right. This museum houses the largest collection of Puerto Rican paintings from the eighteenth century to the 1960s.

El Totem Telurico & Plaza del Quinto Centario

Continue walking towards the left and you will see a plaza with a totem pole or El Totem Telurico.  This is Plaza del Quinto Centenario.

In 1992, to honor the 500 year anniversary of Columbus’ first voyage to the Americas, artist Jaime Suarez created this totem with clay. The clay is from different locations of the Americas, signifying the origins of the people.

Look out toward the ocean and you will see El Morro Fort in the distance.

El Morro Fort

A National Historic Site, completed in 1589, El Morro Fort is a stunning six-level fortress. It successfully protected the city from sea invaders.

The three flags waving at the top commemorate Puerto Rico, the US, and the Spanish military. Spectacular views and interesting historical items make this a fascinating place to visit. On weekends you’ll see families flying kites on the lawn.

La Perla

The colorful neighborhood known as La Perlais located along the ocean to the right of El Morro.

Community leaders have been making efforts toward the growth and development of what has for generations been one of the most underserved and economically disadvantaged sectors of San Juan. This colorful barrio is where the filming for the pop hit “Despacito” took place.

Santa Maria Magdalena de Pazzis Cemetery

The Santa Maria Magdalena de Pazzis Cemetery is the final resting place of many of Puerto Rico’s most prominent natives and residents.

If you plan to visit the cemetery it can be accessed by walking on Calle Norzagaray. At the parking garage, located underneath the Plaza del Quinto Centenario, continue on Calle Del Cementerio. Go through the underground tunnel to reach the cemetery’s entrance.

Plaza de Ballaja & Museo de las Americas

Across from El Morro Fort on Calle Norzagaray, continue walking to Beneficencia.  To fully explore the attractions on this street, you’ll need about 2 hours if you were to visit both museums.

Continue to the Plaza de Ballaja and see the ballajá or military barracks. Built in 1854 for the Spanish troops and their families. This building is home today of the Museo de las Americas containing pre-Columbian to modern art from the Americas.

Plaza de Beneficencia

Walk down Calle Beneficencia and pass the Plaza de la Beneficencia.

In the plaza is a statue in honor of Eugenio Maria de Hostos. Importantly known as “The Great Citizen of the Americas” he was an advocate for Puerto Rico’s independence. Along with being an educator, lawyer, philosopher, sociologist, and writer.

Casa Blanca Museum

Built in 1521, Casa Blanca, built for Juan Ponce de Leon and his family, is the oldest house on the island.

Tucked on the southwest end of Calle Beneficencia and San Sebastian Street, visitors can tour the gardens, mansion living spaces, a display of artifacts, and historic information.

Calle Sol

Walk to San Sebastian Street and turn right on Calle Sol. Bursting with brightly painted houses and flowers, it’s a favorite of mine. A street that’s really a staircase. Now that’s unusual!

La Rogativa statue

At the bottom of Calle Sol, you’ll see La Rogativa statue, made by Lindsay Daen out of bronze. Rogativa means procession.

She created this statue to celebrate a procession of faith, famous in history. The British were about to attack the Spanish army in 1797. The Bishop and towns-women held a procession. Subsequently, the British gave up the attack, thinking the women were Spanish army reinforcements.


Across the street from La Rogativa, there’s a sign that says “limbers.”

This sweet fruit-flavored ice is a nice treat on a hot day. Next to it is a small hallway and gated door. Run by a local family, they’ve been selling these refreshing treats for years. If no one is at the window, just knock loudly or call out a greeting.

Cristo & Forteleza Streets

Go up Las Monjas Street to Cristo Street. On Cristo Street, turn right. Cristo and Forteleza Streets are the main shopping areas. Outlet shops, Puerto Rican handcrafts, unique souvenirs, high-quality jewelry, and artwork can be found here.

La Forteleza

La Forteleza, built between 1533 and 1540

At the very end of La Forteleza Street, is the official residence of the Governor of Puerto Rico. La Forteleza, built to defend the harbor of San Juan is the oldest executive mansion in continuous use and a UNESCO World Heritage Site.

Don’t miss the colorful umbrellas on La Forteleza Street!

Capilla del Santo Cristo

Around the corner from La Forteleza, you’ll see the Capilla del Santo Cristo. Believers who come to the chapel seek miracles for physical illnesses.

Over the years believers have brought tiny silver ornaments, each one representing some ailing part of their body. These small “Milagros,” decorate the walls. They represent the cause of pain for the pilgrim. 

Taking part in a traditional horse race, Baltazar Montanez in 1753, lost control and plunged off the cliffs. The Spanish Secretary of Government, Don Mateo Pratts, cried out, “Christ of Good Health, save him!” The young rider, lived, miraculously saved! That same year Montanez built the small chapel on the exact spot where he fell over the cliff face.

The church is open on Tuesdays and religious days. 

El Parque las Palomas

Next to the chapel on Calle de Tetuan, is Parque las Palomas or Pigeon Park. Here you can purchase bird food and feed the hundreds of pigeons that flock in the park.

Fort de San Cristobal

If you wish to visit Fort de San Cristobal, follow these directions from the Parque Las Palomas.

Walking directions

Completed in 1771, Fort San Cristobal

It should be noted that this fort is brilliantly constructed with a number of different units. Connected by tunnels, if one part is invaded, each unit is self-sufficient. In the dungeon, you can see some of the prisoner drawings on the walls.

The self-guided walking tour of Old San Juan has come to an end.

We hope you enjoyed wandering the blue cobblestone streets with perhaps a piragua in hand. What did you think of the stunning architecture? Did you marvel at the 15-foot thick gate? Were you able to explore one of the incredible forts? They’re reasons enough for exploring this city and embarking on a self-guided walking tour of Old San Juan.

Old San Juan is a perfect place for a self-guided walking tour. With a myriad of historical sites and rich architecture, it’s a perfect way to spend the day.

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