Welcome to Old San Juan!
Welcome to Old San Juan! The cruise port has been seriously renovated in recent years, upping the visitor experience while honoring the historical past. The modern terminals and docks accommodate the largest cruise liners, but I really love how the historic charm is very much intact - even with chain restaurants across the street. One of the standouts to the renovation is the very cool waterfront boardwalk. It stretches along the bay with new sculptures and art that turn a simple walk into a real experience. Each piece tells a story. And seriously, each piece shouts out - wear your sunscreen!Soak in the views of San Juan Bay, the lush landscaping, comfy seating, and be sure and read the plaques. There’s typically local vendors offering crafts and snacks, so you can get a real taste of the island right at port.
From Jail to Garden: Paseo de la Princesa
Built in 1853, Paseo la Princesa is one of the oldest and most beloved promenades in Puerto Rico. Must be named after royalty, right? Nope. It’s actually named after an old prison, La Princesa, which today houses the Puerto Rico tourism Company. What a legacy!The tropically landscaped gardens offer a nice break from the busy streets of Old San Juan, and each of the statues and fountains you see on the way represents a unique story.On weekends the Paseo is lined with food vendors, street performers, and more. It’s a real hub of activity that celebrates the beautiful spirit of Puerto Rico.
Felisa Rincón de Gautier: Snow in San Juan?
The first statue you'll come to honors Felisa Rincón de Gautier, the first female mayor of San Juan. She was in office from 1946 -1968. The people loved her - she even had planes full of snow flown in for kids who had never seen snow, so they could play at Christmas time.Further in this tour, just past the San Juan Gate, there’s a small museum dedicated to her history, travel, and how she helped improve the lives of people in San Juan. Check it out.
Fuente de la Herencia de las Americas
Next up is The Fountain of The Heritage of the Americas. This fountain has 5 bronze statues surrounding it, each one representing the shared heritage of the American continents.The sculptures show figures from Native Americans to European explorers and African slaves. They’re artistically arranged to represent how this huge blending of different cultures evolved into a new, unique history. Is the water flowing? It’s not always turned on, but it symbolizes constant growth and renewal. It’s a good place to think about the complexity of all American identities, and the colonization, migration, and exchange that have created civic pride, as well as cultural richness and diversity.That’s a lot to take in from one simple fountain.
La Princesa: From Dungeon to Art Haven
Imagine turning an infamous colonial prison, which housed up to 240 in horrible, torturous conditions, into not only the beautiful setting for the Puerto Rico Tourism Company, but a peaceful, modern setting to display artwork from local talent. That’s just what they’ve done with La Princesa Jail. Once the site of brutal hangings and torture of political prisoners, today it is a welcoming space - with great air conditioning on a hot day. Love that! Out back and off to the right you’ll see a few of the original jail cells preserved so you can get an idea of just how terrible this place would have been. Built in 1837, it was in operation until - can you believe it - 1965.
Roots That Flow: The Raíces Fountain
Raíces translates to Roots, and Puerto Rico’s roots run deep. The impressive Raíces fountain is one of the projects built to celebrate the 500 year anniversary of the Spanish Arrival to the new world. It represents the unique cultures that make up Puerto Rico’s rich history. Native Taino culture blends with African and Spanish cultures in a beautiful, powerful display, right on the waterfront. Each sculpture tells a story of the island’s legacy. That powerful but calming flow of water? It gives you a moment to reflect, recharge, and of course snap your perfect travel pic. If your cruise schedule fits, this is a great spot to watch - and photograph - a glorious sunset over the bay.
Across the Bay: Defense, and Rum
As you veer right following the path between the harbor and the wall, look across the bay - There’s a group of windmills, and a few red and white smoke stacks. That’s the Bacardi Rum Factory. Though we recommend drinking Don Q Crystal instead of Bacardi, that’s a famous spot with a cool tour. There’s a ferry you can take to get there and back. Also across the bay, there is a small building that was once a leper colony. Look for the signposts to point out the colony, and what was the small fortress where they fired cannons to protect the bay. The side you are standing on is protected by the El Morro fort - it would be tough to get through that cross-bombardment.
Crecemiento Monument: The Legend?
As you continue along the walkway, on the right, you'll see a little park area with a group of spike-looking statues. There's no plaque or real verifiable history that we’ve found covering why it's there or what exactly it represents, but there is an awesome legend saying there was a prison inside the town walls just above this spot. Prisoners would escape by jumping over the wall. Allegedly the Spanish put in a bunch spikes to make sure prisoners didn’t escape, and this sculpture represent that history, without being nearly as deadly. Though it looks pretty brutal. That's just a story, though. Seems like if it were actually true, there would be many more spikes, and they would be closer together. But whatever - that's the working legend.
Signposts: Stop and look around
Before you reach the little pier on the path, take a look at the signposts overlooking the town, the bay, and more. You can see the governor's mansion, among other interesting old buildings, above the walls. If you go out on the pier and look back, you can see all the way down to the Raíces statue, and then all the way along the city wall, out to sea. Looking back toward the fort, you'll see La Puerta de San Juan, or the San Juan Gate - that stop is coming up. On the left, if you look above the city wall, you'll see a very important statue, La Rogativa. We’ll get there, too, but it’s cool to see it from this vantage point.
The Bust of Queen Isabella II
Back on the walkway, there's a huge tree with Spanish moss hanging off its branches. It's makes for quite a setting. Beneath the tree is a statue with the bust of Queen Isabella II of Castile, the woman who supported Columbus and convinced her husband, King Ferdinand II of Aragon, to finance that first trip. Wow. They were also responsible for the Spanish Inquisition, and for the Reconquest of Spain, driving the Muslims back off the Iberian peninsula. The last place they took back? Granada. Site of of some of the most beautiful Islamic architecture.It was also the year that the Jewish population had to either convert to Catholicism, leave Spain, or be put to death.History is a fickle beast. However we feel about it, the world would be different than we know it today without her complicated influence.
City of Invincibility: La Puerta de San Juan
La Puerta de San Juan, the San Juan Gate!It’s enormous - and red! Through this historic entry point went explorers, settlers, religious and government officials, and of course, goods. To begin, it was part of the seriously strong fortification backed by El Morro and San Cristobal forts, and 5 other massive doors that sealed the city walls. Who was attacking? Pirates and foreign navies, to start. When dignitaries arrived, they would moor their boats in the bay, kiss the ground as a blessing, and walk through the gate, straight up to the cathedral to give thanks to Papa Díos after a safe journey. Today, this last remaining gate symbolizes the historical significance and romantic charm of Old San Juan’s cobblestone streets, colorful buildings, and the enduring spirit of the rich Puerto Rican heritage.
Furnace Slag to Ballast: The Cobblestone
Those beautiful blue cobblestones on the streets? They’ve had quite a life, and could tell stories going back hundreds of years. They come from furnace slag from smelting iron for things like forging swords for the military. Toledo, Spain, particularly, was the sword making capitol of the world. Then they repurposed the slag into cobblestones, called Adoquines in Spanish.From there, they were used as ballast in the holds of Spanish ships to keep them steady on their long voyages. When the ships docked in San Juan, the cobblestones were offloaded and used to pave the streets. How cool - they look their best when the sun come out, but they’re still wet, after the rain. On these streets, you’re taking a step back in time - literally.
La Rogativa: The Power of Faith
Rogativa means Procession. This statue immortalizes a story where faith overcame fear. The year was 1797. The British were bearing down on San Juan, there was a good chance that the Spanish could lose control of the city. With a group of women and children, The Bishop of San Juan organized a late night procession complete with torches, bells, singing and praying. From a distance, it looked like Spanish reinforcements had arrived to defend the city. Whether or not that was the goal, it worked. The British packed up and high-tailed outta’ there, thinking they didn’t stand a chance.The story of La Rogativa is a cherished part of Puerto Rico's heritage, showing how a blend of faith, courage, and creativity can triumph over adversity. Don’t forget to take in the incredible views over san Juan Bay! If you get the chance, it’s another great spot for a spectacular sunset.
Elegance Meets History: El Convento Hotel
Next stop? El Convento Hotel. Originally built in 1646 - you heard that right - it was a Monastery, then for about 250 years, it served as a convent for Carmelite nuns. Peace, in the middle of a bustling city! In the 20th century, times changed - as they do. The nuns moved out in 1903, and the historic building took on new roles as a retail store, a dance hall, and even a flophouse. But Robert Woolworth - yes, of the Woolworth department store fame - transformed the crumbling building into a luxurious hotel in 1962. Today, it’s a stunning homage to its past, and blends rich history with modern luxury. Exploring El Convento is a real walk through the past.
Cathedral of San Juan Bautista
What were you doing in 1521? Establishing one of the first cathedrals in the Americas? Right, me too!Nestled in the heart of Old San Juan, the Cathedral e San Juan Bautista really is a timeless testament to Puerto Rico’s history and spiritual heritage. It has both Gothic and Neoclassical architecture, and inside you’ll find the tomb of Puerto Rico’s first governor, Juan Ponce de León. Yup, he’s the guy that went searching for the fountain of youth in Florida. Take a look at the intricately carved woodwork. And those majestic stained glass windows? This beautiful cathedral has been a welcomed spot for centuries.Remember the Gate of San Juan, right down the street? You can see it past the plaza, straight down the front stairs of the church. The Dignitaries arriving from Spain went through the gate and walked up that cobblestone street to give thanks for a safe arrival. Talk about stretching those sea legs!
Monument of Faith: Iglesia de San José
1532. That’s the year the Dominican Order founded the San José Church. With so few examples of 16th century Spanish Gothic architecture in the Western Hemisphere, the church’s ribbed vaults and pointed arches were advanced for their time.It’s been the final resting place for influential figures. Juan Ponce de Leon, the first Governor of the island, was buried here until they moved his remains to a nearby church. The remains of el famoso Puerto Rican painter, José Campeche - the island’s most celebrated painter - are still here. With so much great art and history, that’s a real honor.Talk about bringing the past into the future! A massive restoration began at the turn of the century, and the church re-opened to the public in 2021. Wow. Don’t forget to take a look at the monument in honor of Juan Ponce de León in the plaza. It’s made from melted down cannon balls from a failed British invasion. Talk about up-cycling!
500 Years of Heritage: Plaza del Quinto Centenario
Plaza del Quinto Centenario was built to commemorate 500 years of the island’s complex legacy, including Columbus’ arrival in the New World. Check out El Tótem Telúrico. It stands out from Old San Juan’s historic architecture with a unique granite and clay construction. What gives it such richness and soul across time and distance is that the clay was brought in from different representative sites all across the Americas.That shows, arguably for better or worse, how parts of all these cultures have created the world we live in today, and sets the stage for the lives we’re creating for tomorrow. Take a minute and think about that while you cool off in the fountains on a hot day.
Legacy of Resilience: Cartel de Ballajá
After ten years of construction, the Ballajá Barracks housed up to 1000 Spanish soldiers and their families. Check out the impressive red brick and stone facade - those huge archways and balconies? They keep the air flowing. Imagine being in the Caribbean and not having air conditioning! After construction finished in 1864, the soldiers trained in the beautiful square. Today the architectural masterpiece - showcasing 19th century military style - is used for all kinds of cool things like culinary festivals, literary festivals, art exhibits, family activities and more. Under the United States, the Ballajá was a Military facility until 1936. Today, the ground floor houses the Museum of the Americas, with cultural history and African heritage of the Caribbean. The upper levels? You’ll find dance studios and Art workshops. Like they say, make Fun, Not War.Feel free to take a break and enjoy the gardens outside the Western exit.
Castillo San Felipe del Morro: El Morro Fort
From here, walk up the long sidewalk to the National Park entrance, and explore. Take your time - there are many levels, tons of signboards and plaques to read, and a great historical experiences to discover. Check out the kitchen area, and the cannons, and the lookout areas. The flags up top represent the United States, Puerto Rico, and the Spanish Military.
