Boulevards & Byways

Self Guided Walking Tour of Old San Juan

Much of Old San Juan is made for walking — on sidewalks or medians dotted with benches and shady trees, or along streets lined with its emblematic blue cobblestones — and it is why I want to share with you my self-guided walking tour through Old San Juan.

Whether docking in port from a cruise or just wishing to cross the top 7 things to see in Old San Juan, off your list, this self-guided walking tour of Old San Juan will provide you with an overview of the city, stopping at many of major sites. I’ve included links to Google Maps to help you along your journey.

  • Start at Calle Marina, which is where the cruise ships dock and is especially convenient should you be arriving by ship. It’s also close to a reasonably priced parking garage on PR38, should you be driving into the city.
  • From the marina head west to Calle Comercio toward Plaza Darsenas. 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.
  • Continue walking towards Plaza de Hostos. Here you’ll see a bust of Eugenio María de Hostos, an avid supporter of the independence movement for Puerto Rico and Cuba. Hostos dedicated his life to educational causes and advocating women’s rights to higher education.

Fun Fact

The older streets have a blue-brick called Adoquin‏. Blue stones cast from furnace slag were brought over on Spanish ships as ballast. The characteristic blue color comes from age and moisture.

  • Meander along San Juan’s most beautiful promenade, El Paseo de la Princesa. If it’s a weekend you’ll see vendors selling local art, handmade jewelry, fried treats, and piragua, a shaved-ice made with tropical fruit syrup. Originally created in 1853, the Paseo restored to its 19th-century splendor, features a broad brick walkway leading visitors through a pleasant tree-lined sculptural and garden showcase.
  • It is here you’ll find the headquarters of Puerto Rico’s Tourism Company on the right-hand side. Stop in. This building served as the prison from 1837 to 1960 and the original jail cells can be visited in the back courtyard.
  • As the lovely views of San Juan Bay come into focus, you’ll be greeted by Raíces or Roots Fountain, sculpted by Spanish artist Luis Sanguino. This magnificent bronze fountain celebrates Puerto Rico’s rich cultural diversity and historical heritage through representations of Amerindian, African, and Spanish peoples.
  • If you look across the bay you’ll see a few wind turbines spinning. That’s the Bacardi Rum Factory where you can embark on a tour. If you have a few extra hours, you can take the La Lancha ferry from Pier 2 (near the cruise ship port) to Catano, and then a taxi to the Bacardi Rum Factory.
  • Walking past the Raices Fountain, the walkway turns to the right, and running along the outside of the city walls, is a collection of bronze sculptures called ‘Crecimiento’ a creation, of Carmen Inés Blondet in 1996. Representing the affirmation of life, the shapes, rising from the ground convey the idea that the fragility of growth is only an impression because what is truly important has to be eternal.
  • As you walk further down there is also a sculpture of Queen Isabella in a courtyard shaded by a stately ficus tree with its woody vines.
  • The red city gate or La Puerta de San Juan was built between 1634 and 1638 turning the city of San Juan into an impregnable fortress. 15 feet thick, the words at the top of the gate, “Blessed is he who comes in the name of the Lord,” blesses all visitors as they pass through. This massive door was closed at night to protect the city and its residents from attacks. Out of the three that were built, this is the only one that stands to this day.
  • Continue straight to Caleta San Juan, one of my favorite streets. As you are walking, enjoy the colorful architecture, beautiful Moorish tile, and lovely courtyards of these 400-year-old houses.
  • When visiting the cathedral, be sure to check out the unusual waxed-coated, mummified remains of Saint Pius (San Pio). A soldier, he was the first Christian martyr of the Roman persecutions against the Christians during the first century. Thought to be important to have a real relic of a Christian martyr in the San Juan Cathedral, his remains were brought to Puerto Rico from Spain in 1862.
  • Another notable site to see is the tomb of Ponce De Leon.

Fun Fact

Born in Spain in 1460, Spanish conquistador Juan Ponce de León led a European expedition for gold, which eventually brought him to the southeast coast of what would become the United States. He decided to explore a nearby island, which became Puerto Rico and went on to become its first governor.

Fun Fact

There have been numerous sightings in the guest rooms of The El Convento Hote, a  one-time Carmelite convent. One popular ghost is Doña Ana de Lansos y Menéndez de Valdez, who was the founder of the convent. Doña Ana was its first mother superior, and many say she never left. She and her nuns have been reported to be seen walking the halls of the convent, and the swishing sound of their robes still echoes through this lovely hotel, centuries after Doña Ana’s death
  • When exiting the cathedral, turn around and face it. Admire it’s beauty and then head to the left up Cristo Street or Calle de Cristo. By now you’re probably thirsty. Stop in the tiny bar, El Bate, on the righthand side of the street. One of my favorites, it’s grimy, graffiti-covered walls with business cards hang from the ceiling like a paper windchimes offers inexpensive drinks without those tacky paper umbrellas.
  • Continue up Calle Cristo and on the right you’ll see the oldest church in San Juan, the San Jose Church, built in 1532 and is one of the finest and oldest examples of Gothic influenced architecture built by the Spanish in the New World. It is currently under renovation and is closed to visitors.
  • As the road bears to the left, you will see on the right the Institute of Puerto Rican Culture which houses the largest collection of Puerto Rican paintings from the eighteenth century to the 1960s.

Fun Fact

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

  • This plaza offers spectacular views of El Morro Fort and the ocean beyond. On weekends you’ll see hundreds of kites flying overhead. If you have time, the fort is well worth a visit
  • A National Historic Site and administered by the US National Park Service, El Morro Fort is a six-level fortress was completed in 1589 to protect 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.

Fun Fact

The neighborhood known as La Perla is located along the ocean to the right of El Morro. A  poor barrio clinging to a steep hillside between Old San Juan and the sea is where the video for the pop hit “Despacito” was filmed.

Fun Fact

In the distance you will also see a cemetary. The Santa Maria Magdalena de Pazzis Cemetery and is the final resting place of many of Puerto Rico’s most prominent natives and residents. Before it was designated an official cemetery, there was a “Cementerio Provisional” on the same grounds, dating to 1845.  TIP: If visiting the cemetary head west on PR-25R (Avenida Luis Muñoz Rivera) and take Calle Norzagaray until you reach the parking garage located underneath the Plaza del Quinto Centenario (GPS: 18.468338, -66.119170). Then you can walk down Calle Del Cementerio, through the underground tunnel to reach the cemetery’s entrance.

  • After you have completed your tour of the fort or if you choose not to go to the fort, continue to the Plaza de Ballaja and see the ballajá, or military barracks. Built in 1854 for the Spanish troops established on the island and their families, this building is home today of the Museo de las Americas – which contains pre-Columbian to modern art from the Americas.
  • After you exit, cross the Plaza de Beneficencia and Casa Blanca will be on your right, at the end of San Sebastian Street. Casa Blanca was built in 1521 as a “strong-house” for Ponce de Leon, but he died before it was completed. Today it is a National Historic Monument and a museum.
  • When you leave Casa Blanca, turn onto San Sebastian Street, turn right and go down the steps to Calle Sol, another one of my favorites streets, or should I say a street of steps. It’s a pretty area filled with brightly painted houses and flowers bursting with color.
  • Once you reach the bottom of Calle Sol you’ll see La Rogativa statue.  Made out of bronze by Lindsay Daen, rogativa means “The Procession,” commemorating a procession of faith held by the Bishop and townswomen during an attack of the Spanish army in 1797. The British thought they were Spanish Army reinforcements and gave up on the attack.
  • Across the street from La Rogativa, there’s a sign that says “limber,” sweet fruit-flavored ice. Next to it is a small hallway and gated door. While you might think it looks a little sketchy, there’s nothing to fear. 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
  • Go up Las Monjas Street to Cristo Street. Once on Cristo Street, turn right. Cristo and Forteleza Streets are the main shopping areas that include outlet shops, stores with Puerto Rican handcrafts, and a fun assortment of stores with unique souvenirs, high-quality jewelry, and even some excellent art.
  • At the end of La Forteleza Street the colorful umbrellas, which have become an attraction in itself, drawing an increase in visitors to this area.
  • It’s also where you’ll find La Forteleza, the official residence of the Governor of Puerto Rico, Built between 1533 and 1540 to defend the harbor of San Juan it’s the oldest executive mansion in continuous use in the New World and a UNESCO World Heritage Site.

Fun Fact

The story goes that during the San Juan Bautista celebrations of 1753, a rider in the traditional horse race, Baltazar Montanez, lost control of his horse plunging to the cliffs below. The Spanish Secretary of Government, Don Mateo Pratts is understood to have 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 face.

Believers who come to the chapel seeking miracles for physical illness. Over the years they have brought tiny silver ornaments, each one representing some ailing part of the body. These small “milagros” decorate the walls, miniature silver legs, arms, hearts or lungs representing the cause of pain for the pilgrim. 

Today the church is only open on Tuesdays and religious days. 

  • Next to the chapel on Calle de Tetuan, is El Parque las Palomas or pigeon park. Here you can purchase bird food and feed the hundreds of pigeons that flock in the park. It’s a sight to be seen.
  • From here, if you have the time and the energy You can walk to Fort San Cristobal, built in 1634, and completed in 1771. At150 feet high it was used to protect the city from sea and land invasions. The fort was constructed with a number of different units each connected by tunnels and each self-sufficient if another part was invaded. In the dungeon, you can see some of the prisoner drawings on the walls. A  National Historic Site is administered by the US National Park Service.

Old San Juan is a perfect place for a self-guided walking tour. With a myriad of historical sites and rich architecture, you’ll never find a better way to spend the day.

If you have time before you return to your hotel or cruise ship consider taking a sunset sail in San Juan Bay.

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