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  • Writer's pictureMark Vogel

Walking the Blue Cobblestone Streets of Old San Juan, Puerto Rico

Old San Juan, Puerto Rico


Old San Juan, Puerto Rico
Old San Juan, Puerto Rico

As a seasoned traveler, I've been lucky enough to have the sun-kissed sands of Puerto Rico beneath my feet more times than I can count. While the sandy beaches and nightlife of San Juan never fail to impress me, it's the unique charm of Old San Juan that brings me back again and again.


Book a Walking Tour: Old San Juan Walking Tour




“Old San Juan is much more than just a historic city; it's a beautiful maze of colorful streets and plazas, each holding a piece of Puerto Rico's heart.”

This historical part of the city is just a short Uber ride from the modern Condado and Isla Verde neighborhoods. Start at the bustling Plaza Arturo Somohano, where the aroma of freshly brewed coffee from the local Starbucks sets the tone for an exciting day. Near this plaza, the Plaza Colón beckons with its bronze statues and the magnificent Antiguo Casino de Puerto Rico. The Casino, an architectural gem from the early 20th century, offers a glimpse into the island's colonial past.



Blue Cobblestone Streets and Brightly Painted Buildings


As you stroll down Fortaleza Street, a lively display of shops and restaurants welcome you. This bustling thoroughfare, set on the famous blue cobblestone streets, leads you straight to La Fortaleza. Serving as the governor's mansion, La Fortaleza is the oldest executive mansion still in use in the Western Hemisphere, painting a vivid picture of the island's rich history.


The buildings in Old San Juan are a beautiful palette of bright colors that reflect the island's tropical spirit. A walk around the city feels like a moving artwork, a blend of colonial architecture and Caribbean flair. One unique spot to visit is the Parque de las Palomas. This park, home to hundreds of pigeons, offers a unique experience as the birds fly around, often coming close enough to land on outstretched arms.


My journey usually continues to the Plaza de Armas, a historic square that has been the city's social and political center since the 16th century. The beautiful fountain, the four statues representing the four seasons, and the City Hall offer a quaint charm that adds to the plaza's allure.



A little further is the Plaza de la Catedral, where a sweet surprise awaits: a sculpture called Gato Jirafo by artist Jorge Zeno. The 5-foot-tall bronze sculpture depicts a cat with the neck of a giraffe. In an adorable coincidence, on one of my trips, I found a real cat lounging under the statue, hiding from the warm sun.


A walk down to the Puerta de San Juan, the city gate that once guarded the entrance to the fortified city, offers a humbling sense of history. After stepping through this gate, the scenic path along the waterfront is amazing, with old majestic trees adding a touch of timeless beauty.


You will then make your way to the Fuente Raíces fountain and Paseo de La Princesa, a lovely promenade boasting local art, food, and music. From here, it's a short walk towards the Marina, where gigantic cruise ships often dock, creating a mesmerizing backdrop.


One of my memorable adventures from here was taking a ferry ride across the bay to Catano. The view of San Juan from the water was breathtaking and well worth the trip.


After an eventful day, you can stop by the Sheraton Old San Juan for a welcome respite. There's something comforting about sinking into a plush seat, savoring a cool drink, and reveling in the hotel's air conditioning after a long day of exploration.



The Magnificent El Morro


One of the unforgettable experiences Old San Juan offers is a visit to the fortresses. Castillo San Felipe del Morro, a 16th-century citadel, offers panoramic views of the ocean and the city. The fortress, affectionately called El Morro, tells tales of maritime history, piracy, and warfare, making it a must-see.


The first thing you'll notice is its commanding location, situated atop a high point overlooking the entrance to San Juan Bay. This strategic positioning offered the Spaniards a vantage point to deter potential invaders.


Walking towards the entrance, you'll see a vast, green field known as El Morro's esplanade. These grounds once served as a military parade area, but today they're a popular spot for flying kites, thanks to the refreshing Atlantic winds. Look up, and you might see the sky dotted with colorful kites, juxtaposed against the blue canvas of the sky.


As you enter the fortress, you'll step into a labyrinth of tunnels, barracks, towers, and dungeons. The first level, known as the Main Plaza, was where soldiers and workers lived and labored. Imagine their life here, with the distant sound of the ocean as a constant backdrop.



As you venture deeper, you'll see the cannon water battery, known as the Santa Barbara Battery, where large cannons once stood, pointing towards the ocean, ready to blast any enemy ships daring to approach. You'll get to see the "garitas" or sentry boxes, which are now an iconic symbol of Puerto Rico.


The next stop is the lighthouse, added to El Morro by the United States in 1908. From here, the panoramic view of San Juan Bay and the Atlantic Ocean is simply breathtaking. It's a fantastic spot to snap a memorable photo.


Descending into the depths of the fort, you will find the dungeons. As you observe the etchings on the dungeon walls, try to imagine the captured sailors and soldiers who were once imprisoned here, carving these drawings as they dreamt of freedom.


Finally, you will climb up to the upper levels of El Morro, where six levels of defense were set up. The height gives you a sense of the strategic advantage the fort provided, allowing an unhindered view of incoming enemy vessels.


El Morro isn't just a fortress; it's a testament to human tenacity, strategic ingenuity, and the rich tapestry of Puerto Rican history. As you navigate its centuries-old tunnels and ramparts, I hope you'll come to appreciate its importance as I do.


If you still have some time and energy left, take a stroll to another remarkable fort, Castillo San Cristóbal. This largest Spanish fort in the New World was built to protect the city from land-based attacks and offers another fascinating dive into the island's colonial past.


Old San Juan is much more than just a historic city; it's a beautiful maze of colorful streets and plazas, each holding a piece of Puerto Rico's heart. A visit here is like stepping back in time, a journey that keeps calling me back, one cobblestone step at a time.



Book a Walking Tour: Old San Juan Walking Tour

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