One of the best ways to see the city of Old San Juan, Puerto Rico is to walk. Stroll upon the blue cobblestone streets of this oldest city in America and see pastel-colored colonial architecture, historic forts, quaint museums, monuments, and charming plazas with cafes and restaurants.

The city is layered with hundreds of years of Spanish, Taino, and African influences. Take this self-guided walking tour of Old San Juan and immerse yourself in the culture and cuisine of this charming city.

Self-Guided Walking Tour of Old San Juan

Links to Google Maps are included to help you along your journey.

Welcome to Old San Juan!

Start Your Walking Tour at Calle Marina

This walking tour starts at Calle Marina, which is where the cruise ships dock. If you are driving into the city, there’s a reasonably priced parking garage on PR38. Park in the garage and walk toward the waterfront. Enjoy the beautiful view of the bay!

Plaza Darsenas & Casita de Rones Bar

From the marina head west, with the bay on your left, to Calle Comercio. You will come upon Plaza Darsenas and the Casita de los 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 is cbum natural 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

Continue strolling on the path toward San Juan’s most beautiful promenade, El Paseo de la Princesa. Originally created in 1853, the Paseo, features a broad brick walkway. It leads visitors through a pleasant tree-lined sculptural and garden showcase.

Look up and see the remains of the original city walls. La Muralla, a UNESCO World Heritage Site is nearly 400 years old. By 1873 masonry walls fully encircled the city and the fortification defended the entire islet. It was considered one of the best fortified cities in the Caribbean and consisted of lookouts and defensive positions.

On weekends, vendors sell local art, handmade jewelry, fried treats, and piragua, a shaved-ice made with tropical fruit syrup.

Puerto Rico Tourism Company

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

Raices Fountain

Along with the lovely views of San Juan Bay you will see the beautiful Raíces or Roots Fountain. The fountain celebrates Puerto Rico’s rich cultural diversity and historical heritage. Sculpted by Spanish artist, Luis Sanguin, Amerindian, African, and Spanish peoples are represented.

Bacardi Factory

Look across the bay you’ll see a few wind turbines spinning. That’s the Bacardi Rum Factory. 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 and 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 I of Spain in a courtyard next to the city wall. It’s shaded by a stately ficus tree.

Self-Guided Walking Tour of Old San Juan

La Puerta de San Juan

As you continue to follow the path you will come upon an immense red gate or La Puerta de San Juan. Build between 1634 and 1638, when the wall was built around the entire city, this massive door was closed at night to protect the city and its inhabitants.

Out of the three that were built, this is the only one that stands to this day. As you walk through the gate, notice the 15-feet thick walls.

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

Walk through the gate and continue straight on San Juan Street or Caleta San Juan. Notice the colors and architecture of these 400-year old homes. The beautiful Moorish title and hidden courtyards make this my favorite street to take a stroll.

Cathedral de San Juan Bautista

At the top of San Juan Street is the graceful gothic Cathedral de San Juan Bautista or the Cathedral of Saint John the Baptist. It is the second oldest church in the western hemisphere and oldest church on US soil. The history of the church begins in 1521 with the beginnings of the Spanish colonialization of the island.

The tomb of Ponce de Leon, the first governor of Puerto Rico is housed in this church. A Spanish conquistador, he led the first European expedition for gold to the Americas in addition to a small island to be later named, Puerto Rico. It was in 1509 he took office as the first Governor of Puerto Rico by appointment of the Spanish crown.

El Convento Hotel

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

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. It is said that 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, this place is a welcome respite from the heat.

San Jose Church

Continue walking 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. It has recently been renovated.

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 Perla is 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. Please note that this is a local neighborhood, not a tourist attraction, so respect the privacy of those who live here.

Santa Maria Magdalena de Pazzis Cemetery

Before you reach El Morro, you will see the beautiful Santa Maria Magdalena de Pazzis Cemetery is the final resting place of many of Puerto Rico’s most prominent natives and residents; artists, politicians, musicians, and painters.

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

Across from El Morro Fort on Calle Norzagaray, continue walking to Beneficencia to the Plaza de Beneficencia. 

Plaza de 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 and an educator, lawyer, philosopher, sociologist, and writer.

Plaza de Ballaja & Museo de las Americas

To fully explore the attractions on this street, you’ll need about 2 hours if you were to visit both museums.

Museo de las Americas

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.

Casa Blanca Museum

Continue walking and tucked on the southwest end of Calle Beneficencia and San Sebastian Street on the right, is Casa Blanca, built in 1521 for Juan Ponce de Leon and his family. It is the oldest house on the island. Visitors can tour the lovely gardens, mansion living spaces, a display of artifacts, and historic information.

Side Trip to La Factoria Bar

If you want to make a stop to the famous La Factoria Bar, don’t turn on Calle Sole just yet. Stay on San Sebastian Street and walk 2 blocks. La Factoria is rated as one of the worlds 50-best bars in North America. A labyrinth of six unique rooms, each with different menus and themes, cater to guests looking for a slightly different experience. 

Calle Sol

From San Sebastian Street turn onto 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. This statue was created to celebrate a famous procession of faith in history.

When the British were about to attack the Spanish army in 1797, the Bishop and towns-women came up with a brilliant plan to protect the city. They held a procession, and subsequently, the British gave up the attack thinking the women were Spanish army reinforcements.

Limber

Across the street from La Rogativa, there’s a sign that says “limbers.” Next to it there is a small hallway and gated door. Run by a local family, they’ve been selling these sweet-fruit flavored ice treats for years. If no one is at the window, just knock loudly or call out a greeting.

Self-Guided Walking Tour of Old San Juan

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

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.

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.

The legend says that Baltazar Montanez, in 1753, took part in a traditional horse race, 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. He was miraculously saved, they believed! That same year Montanez built the small chapel on the exact spot where Montanzez fell over the cliff.

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. 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.

You can choose to END your walking tour here, or continue to on to Fort de San Cristobal, which will put you near the parking garage on PR38.

Fort de San Cristobal

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

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. Be sure to take in the beautiful views of the Atlantic Ocean.

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?

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.

More things to do in Old San Juan:

Take a Sunset Sail in Old San Juan Bay

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