Boulevards & Byways

Self Guided Walking Tour of Old San Juan

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 favorite self-guided walking tour through Old San Juan.

Whether docking in port from a cruise or in town 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 a fantastic overview, stopping at many of the city’s major sites. Feel free to follow along. I’ve included links to Google Maps to help you find your way.

  • Start at Calle Marina, which is where the cruise ships dock, 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. 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 ballasts. 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. 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 the Bacardi Rum Factory and can embark on a tour. 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.
  • When you arrive at the city gate or La Puerta de San Juan, make note of the walls. This passageway is 15 feet thick. Between 1634 and 1638, the city of San Juan was turned into an impregnable fortress with the building of its walls. This massive door was closed at night to protect the city and its residents from attacks by land or
    sea. Out of the three that were built, this is the only one that stands to this day. “Blessed is he who comes in the name of the Lord” welcomes and blesses all visitors as they pass through the gate.
  • 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.
  • At the top of the street, you will be greeted by the graceful Cathedral de San Juan Bautista or the Cathedral of Saint John the Baptist. When visiting make sure you see the tomb of Ponce de León and 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.

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.

  • The El Convento Hotel  is on the diagonal corner to the cathedral. Stop in the view the beautiful architecture. There’s a restaurant inside too.

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.
  • Continue up Calle Cristo and on the right you’ll see the oldest church in San Juan, the San Jose Church, built in 1521. It is currently under renovation and is closed to visitors.
  • As the road goes 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.
  • Bear left and you will see a plaza with a totem pole or El Totem Telurico.  This is Plasa del Quinto Centenario.

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. If you have time, the fort is well worth a visit. A National Historic Site and administered by the US National Park Service, this 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.

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.

  • The neighborhood known as La Perla, is located right in between the forts of San Cristobal and El Morro, two of the most significant historic landmarks. 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.
  • 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.
  • There is a small window across the street from the statue that says “limber,” a 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. You’re now in the shopping district which includes brand name outlet stores, shops with handmade items, and a fun assortment of stores with Puerto Rican handcrafts.
  • When you get to Fortaleza Street, turn right. At the end of the street, you’ll see a blue building – La Fortaleza – which was built in the early 1500′s as the first fort to protect the city from Carib Indian sea invaders. In 1846, the building was remodeled from a
    fort to the mansion you see today. It’s the oldest governor’s mansion still used in the Western Hemisphere and a World Heritage Site, it’s open Monday through Friday from 9:00 until 3:30 pm., but you need to make a reservation. You can call 1-787-721-7000 ext. 2358 or stop in at the yellow building on the left side of the street a few doors up from the Fortaleza. Tours last about 40 minutes.
  • Return to Cristo Street, turn right, and go to the end of the street. This beautiful old chapel is Capilla del Cristo (Cristo Chapel). Built in 1753, it’s dedicated to the Cristo of Good Health. Buy the piece of silver (promesas), which most represents the area of your body for you have a health issue, and leave it at the church as an offering.
  • If you look to your right when you are facing the chapel you’ll find Parque de las Palomas (Pigeon Park). Here you will be able to feed the hundreds of pigeons that make this park home.
  • At the end of Fortaleza Street bear left toPlaza de Colon with the statue of Christopher Columbus. The plaza is surrounded by restaurants and cafes. The statue, commemorating the 400th anniversary of the discovery of Puerto Rico, is surrounded by bronze plaques on the base representing the ocean journey, the arrival of Christopher Columbus, and the meeting of the indigenous people.
  1. 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, it 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, explore for yourself. You’ll never find a better way to spend the day.

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