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Meandering the Cobblestone Streets of Old San Juan, Puerto Rico
Published by Connie Motz, Writer
Country: Puerto Rico 
The Experience
Even if you only have a few hours to visit as a cruise ship passenger, or if you’ve only got days to spare, walking the cobblestone streets of Old San Juan in Puerto Rico is a must for any visitor who wants to explore the island’s wonderful history.
Spanning a mere seven square blocks, the walled city of Old San Juan offers an abundant selection of shops, galleries, restaurants, bars and discos, set among its Spanish Colonial buildings and World Heritage sites. Along the way visitors will view an array of pastel coloured buildings, wrought iron balconies teeming with flowers, and those beautiful winding cobblestone streets.
An Old San Juan walking tour starts at Plaza de la Darsena, which is to the left of the pier if you’re embarking off one of the many cruise ships that visit the island. Within Plaza de la Darsena is La Casita Tourism Information Center where you can pick up an Old San Juan map along with other Puerto Rico visitor information. The Plaza is also home to many local artisans displaying their work for the abundance of cruise passengers who appear almost daily.
From La Casita, make your way on Calle Comercio to the east, which passes by the piers. After a few blocks, make a left heading for Plaza de San Jose where locals gather to enjoy their day; and at the end of the plaza to the left, take a right onto Calle Tetuan. Then, after crossing Calle Fortaleza, you’ll be at the much larger Plaza Colon with its notable statue of Christopher Columbus.
Walk across the plaza onto Calle San Francisco, turn to the right and follow the street to the end until you arrive at Calle Norzagaray. Puerto Rico’s largest fort, San Cristobal, is on the right. Dating back to its completion in 1783, San Cristobal is designated both as a U.S. National Historic Site and a UNESCO World Heritage Site.
Further along your Old San Juan walking tour, Calle Norzagaray turns into Del Valle Boulevard where you’ll view smaller ocean side homes of La Perla to the right and beautiful architecture to the left. In the distance you will see the imposing fortress of Castillo de San Felipe del Morro, more commonly known as El Morro.
This second National Historic Site with a World Heritage designation is set at the gateway to the Puerto Rico. El Morro fortress stands proudly displaying its six levels, including passageways, chambers, barracks, and stunning ocean views from the domed sentry boxes known as garitas. With substantial 18” thick walls, it’s easy to see how the fortress withstood foreign enemies for over 400 years.
Adjacent to El Morro, visitors can view from above the elaborate and beautiful Cemetery Maria Magdalena de Pazzis on the edge of the Caribbean Sea. This makes for a perfect photo op of the cemetery as well as El Morro.
Taking a straight path from El Morro will lead you to Plaza de Ballaja with old barracks that have now been converted into museums, including the Museum of the Americas that is home to a series of unique hand-carved saint statues. To the right across the plaza, you’ll find the National Historic Monument of Casa Blanca that was built for Ponce de Leon in the early 1500s.
Upon leaving Casa Blanca, follow Calle San Sebastian to Calle del Cristo, taking a right and heading down the hill until reaching Calle Fortaleza. On the right is a blue building also built in the early 1500s known as La Fortaleza, or the Governor’s Mansion. Heading back to Calle del Cristo, visitors will find the small Cristo Chapel that offers amazing views of the Caribbean Sea and piers below.
To the left of the chapel is Parque de las Palomas (Pigeon Park), which is filled with flocks of pigeons and, unfortunately, an abundance of pigeon poop. This quaint park is a popular photo op stop for families and also provides great views of Plaza de la Darsena below. From here it’s a simple downhill walk back to the starting point near the cruise pier.
Once you’re back at the pier, if you’d like to continue exploring the beautiful city of Old San Juan, take a right onto Paseo de la Princesa as it follows the waterfront and makes its way along to El Morro.
Spanning a mere seven square blocks, the walled city of Old San Juan offers an abundant selection of shops, galleries, restaurants, bars and discos, set among its Spanish Colonial buildings and World Heritage sites. Along the way visitors will view an array of pastel coloured buildings, wrought iron balconies teeming with flowers, and those beautiful winding cobblestone streets.
An Old San Juan walking tour starts at Plaza de la Darsena, which is to the left of the pier if you’re embarking off one of the many cruise ships that visit the island. Within Plaza de la Darsena is La Casita Tourism Information Center where you can pick up an Old San Juan map along with other Puerto Rico visitor information. The Plaza is also home to many local artisans displaying their work for the abundance of cruise passengers who appear almost daily.
From La Casita, make your way on Calle Comercio to the east, which passes by the piers. After a few blocks, make a left heading for Plaza de San Jose where locals gather to enjoy their day; and at the end of the plaza to the left, take a right onto Calle Tetuan. Then, after crossing Calle Fortaleza, you’ll be at the much larger Plaza Colon with its notable statue of Christopher Columbus.
Walk across the plaza onto Calle San Francisco, turn to the right and follow the street to the end until you arrive at Calle Norzagaray. Puerto Rico’s largest fort, San Cristobal, is on the right. Dating back to its completion in 1783, San Cristobal is designated both as a U.S. National Historic Site and a UNESCO World Heritage Site.
Further along your Old San Juan walking tour, Calle Norzagaray turns into Del Valle Boulevard where you’ll view smaller ocean side homes of La Perla to the right and beautiful architecture to the left. In the distance you will see the imposing fortress of Castillo de San Felipe del Morro, more commonly known as El Morro.
This second National Historic Site with a World Heritage designation is set at the gateway to the Puerto Rico. El Morro fortress stands proudly displaying its six levels, including passageways, chambers, barracks, and stunning ocean views from the domed sentry boxes known as garitas. With substantial 18” thick walls, it’s easy to see how the fortress withstood foreign enemies for over 400 years.
Adjacent to El Morro, visitors can view from above the elaborate and beautiful Cemetery Maria Magdalena de Pazzis on the edge of the Caribbean Sea. This makes for a perfect photo op of the cemetery as well as El Morro.
Taking a straight path from El Morro will lead you to Plaza de Ballaja with old barracks that have now been converted into museums, including the Museum of the Americas that is home to a series of unique hand-carved saint statues. To the right across the plaza, you’ll find the National Historic Monument of Casa Blanca that was built for Ponce de Leon in the early 1500s.
Upon leaving Casa Blanca, follow Calle San Sebastian to Calle del Cristo, taking a right and heading down the hill until reaching Calle Fortaleza. On the right is a blue building also built in the early 1500s known as La Fortaleza, or the Governor’s Mansion. Heading back to Calle del Cristo, visitors will find the small Cristo Chapel that offers amazing views of the Caribbean Sea and piers below.
To the left of the chapel is Parque de las Palomas (Pigeon Park), which is filled with flocks of pigeons and, unfortunately, an abundance of pigeon poop. This quaint park is a popular photo op stop for families and also provides great views of Plaza de la Darsena below. From here it’s a simple downhill walk back to the starting point near the cruise pier.
Once you’re back at the pier, if you’d like to continue exploring the beautiful city of Old San Juan, take a right onto Paseo de la Princesa as it follows the waterfront and makes its way along to El Morro.
When to Go to Old San Juan
Odds n' Ends
La Casita Tourism Information Center is open seven days a week from 8:00 a.m. to 8:00 p.m., and offers a free rum sample after 1:00 p.m. (excluding Thursday/Friday)
Built in 1592, Cathedral de San Juan is located near Hotel El Covento along Calle Cristo and Calle Sol
Along the way, don’t miss stopping at:
Pablo Casals Museum, Calle San Sebastian
San Juan Museum, Calle Norzagaray
Felisa Rincon de Gautier Museum, Calle de San Juan
Butterfly Gallery, Calle de la Cruz
Strolling along Paseo de la Princesa in the evening with local families is a wonderful option to ending the day
Built in 1592, Cathedral de San Juan is located near Hotel El Covento along Calle Cristo and Calle Sol
Along the way, don’t miss stopping at:
Pablo Casals Museum, Calle San Sebastian
San Juan Museum, Calle Norzagaray
Felisa Rincon de Gautier Museum, Calle de San Juan
Butterfly Gallery, Calle de la Cruz
Strolling along Paseo de la Princesa in the evening with local families is a wonderful option to ending the day
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