Boulevards & Byways

Self Guided Walking Tour of Old San Juan

Self Guided Walking Tour of Old San Juan

It’s a tradition of mine. Whenever I’m in Puerto Rico I visit Old San Juan. This colorful city is exquisitely inviting, however, it’s not just the turquoise seas and brightly painted colonial homes beckoning me back again and again. 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 are 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.

I always start at Calle Marina, which is where the cruise ships dock 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.  This restaurant has a bar and small shop that serves as a promotion center for the rums of Puerto Rico.
  • Continue walking towards Plaza de Hostos. Here there is 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. If it’s a weekend enjoy the vendors selling local art, handmade jewelry, and fried treats.  Grab a ‘piragua,’ a shaved‐ice made with tropical fruit syrups.
  • Next, meander along San Juan’s most beautiful promenade, El Paseo de la Princesa. Originally created in 1853, the Paseo has been restored to its 19th century splendor, features a broad brick walkway leading its visitors through a pleasant tree-lined sculptural and garden showcase.
  • It is here you’ll find the headquarters of Puerto Rico’s Tourism Company. This building served as the prison from 1837 to 1960. Today, the restored ‘La Princesa’  houses exhibits of Puerto Rican art and the original jail cells can be visited in the back courtyard.
  • As you begin to see the lovely views of San Juan Bay, 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 on another day by taking the La Lancha ferry from Pier 2  to Catano and then a taxi to the rum factory.
  • You will pass the sculpture which looks likes “Spikes.” I haven’t been able to find any information about what these spikes represent however, if any of you find out, drop me a note and I’ll add the information to this post. As you walk further down there is a also a sculpture of Queen Isabella in a courtyard shaded by a stately ficus tree.
  • When you arrive at the city gate or La Puerta de San Juan, make note of the walls. This passage way 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. This entry way welcomes all visitors with the words, “Blessed is he who comes in the name of the Lord.”
  • Continue straight to Caleta San Juan, one of my favorite streets. As you are walking, enjoy the colorful architecture, beautiful Moorish tile work, 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 Cathedral of Saint John the Baptist. This historic landmark is located at Calle del Cristo #151-153, near the beautiful El Convento Hotel. When visiting make sure you see the tomb of Ponce de León and the unusual waxed-coated, mummified remains of Saint Pius (San Pio). He was the first Christian martyr of the Roman persecutions against the Christians during the first century. A solider, he was executed for his faith. 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.
  • 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.
  • At the Plaza 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. The Institute of Puerto Rican Culture can also be found here and houses the largest collection of Puerto Rican paintings from the eighteenth century to the 1960s.
  • When Cristo Street ends at ???) go left to the left to Plaza del Quinto Centenaro. You’ll know you reached it when you see a totem pole, or El Totem Telurico. 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 areas of the Americas and is meant to signify the origins of the people in these areas.
  • This plaza offers great views to 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.
  • 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.
  • When you exit, cross the Plaza de Beneficial and Casa Blanca will be on your right, at the end of San Sebastain 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 turn left or right??? to see La Rogativa statue.  Made out of bronze by Lindsay Daen, rogativa means “The Procession,” commemorating a procession of faith in 1797 by the Bishop and townswomen as they held touches and chanted through town. 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, it’s a refreshing treat. You might think it looks a little sketchy, but there’s nothing to fear. 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 Puerto Rican souvenir stores.
  • 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 appropriate body-part-shaped pieces of silver (promesas) for which you have a health issue, and leave it at the church as an offering.
  • If you turn to your right , you’ll find Parque de las Palomas (Pigeon Park). Here you will be able to feed hundreds of pigeons that make this park home.
  • At the end of Fortaleza bear left to Plaza 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 providing representations of 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, at 150 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, there’s no other way I’d rather spend the day in Old San Juan. Take this self guided tour of Old San Juan and explore for yourself. You’ll never find a better way to spend the day.





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