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How To Spend One Day In Old San Juan

Old San Juan is an old city reminiscent of other global areas. Mix the colorful buildings of Cuba, the cobblestone streets of Belgium, and the historic fort of the Tower of London, and you’ve arrived in Old San Juan, Puerto Rico.

I remember sailing into Puerto Rico on a back-to-back eastern and western Caribbean cruise. Its old-world charm captivated me, and I couldn’t wait to explore its cobblestone walkways. While I only had one day in Old San Juan, its history and beauty encouraged me to soak it all up.

Old San Juan is a UNESCO World Heritage Site and one of the oldest cities in America. It’s best explored on foot, as driving the narrow streets is challenging.

Green iguana at El Morro fort in Old San Juan

While most travel to the Caribbean for its sandy beaches, San Juan has much more to offer. After one visit, you’ll fall in love with romantic San Juan, as I did.

Things To Do In Old San Juan

I stopped in Puerto Rico on a back-to-back cruise of the eastern and western Caribbean. It was a magical vacation where I enjoyed a private beach club in Cozumel, swimming with stingrays in Grand Cayman, ziplining in Roatan, and many other excursions.

Cruising into Old San Juan, most ships dock at Terminal 4, a stone’s throw from all significant Puerto Rico landmarks. Here are the best things to do during a one-day itinerary of Old San Juan.

Tour Castillo San Felipe del Morro

  • Location: 501 Calle Norzagaray / Hours: 9 am to 6 pm daily
Lighthouse at Castillo San Felipe del Morro
El Morro lighthouse

Renowned for its rich history, visiting one of San Juan’s old fortresses, a San Juan National Historic Site is a must. El Morro’s façade and grassy esplanade is stunning. Older than Castillo San Cristobal, the fort is showing its age with weathered erosion.

However, with its 16-foot-deep walls that tower 140 feet above the ocean, it served well as a defense fortification. Inside, I toured the Plaza de Armas and small rooms that served as living quarters.

El Morro is vast and spreads out over six levels. It took me a couple of hours to explore and learn its history. A steep walkway took me from the Plaza to a lower level featuring the batteries and sentry boxes called garitas.

Cannon batteries at El Morro
The battery level of El Morro

From the fort, there are sweeping views of the ocean, San Juan Cemetery, and beyond. Behind Santa Maria Magdalena de Pazzis is a sketchy neighborhood called La Perla, which tourists best avoid.

Explore Castillo San Cristobal

  • Location: 501 Calle Norzagaray / Hours: 9 am to 6 pm daily


While Castillo San Felipe del Morro, or El Morro, was built to stop an ocean invasion, Castillo San Cristobal’s structure was to prevent land attacks from the east. The imposing fortress is within walking distance from the cruise terminal and should only take ten minutes.

Built by Spaniards, Castillo San Cristobal has remained a massive stronghold for centuries. Named after Saint Christopher, the Patron Saint of Travelers, it’s America’s largest fort.

Castillo San Cristobal, Puerto Rico
Castillo San Cristobal

Expect to spend about two hours on a self-guided tour. San Cristobal, like El Morro, is part of the San Juan National Park Service. So, a US 10.00 entrance fee is a 24-hour pass, suitable for both venues.

Take time to explore the myriad of tunnels, dungeons and grottos. During my wandering, I discovered numerous green iguanas sunning themselves on the warm stone walls. I was surprised at their colors and enormous size.

Visit Santa Maria Magdalena de Pazzis

  • Location:  Calle Cementerio / Hours: 7 am to 3 pm daily

Visiting a cemetery might not seem like the ideal thing to do on vacation. However, Santa Maria Magdalena de Pazzis holds the burial spots for numerous notable Puerto Ricans.

Santa Maria Magdalena de Pazzis
Santa Maria Magdalena de Pazzis

Located on the coast between San Cristobal and El Morro, it’s easily added to your one-day itinerary. I stopped by on my way back from seeing El Morro. Access to the cemetery is by way of a tunnel.

The tombstones are predominately white, and even in their deteriorating condition, the graveyard is spectacular. Initially constructed in the mid-1800s, some of the memorials showed their age, and Hurricanes damaged others.

In the center of the compact cemetery, a tiny red-domed chapel provides shade from the scorching sun. Browsing the Genevan memorials and stunning sculptures gave me a glimpse into the lives of influential Puerto Ricans.

The angel sculptures are particularly spectacular, and some of the tombstones are enormous by North American standards.

An angel memorial at Santa Maria Magdalena de Pazzis
An angel memorial at Santa Maria Magdalena de Pazzis

Discover La Puerta de San Juan

  • Location: Calle Caleta De San Juan

An ancient city wall surrounds much of downtown and has a door or entrance. La Puerta de San Juan, or San Juan Gate, is the original colonial entrance to Old San Juan. Walking the La Princesa leads to the San Juan Gate.

From the 1500s to 1800s, travelers passed through this gate when entering and leaving the protected city. Above the entrance, the Latin inscription “Benedictus qui venit in nomini Domini” means “Blessed are those who come in the name of the Lord.”

Named after Saint John the Baptist, the San Juan Gate is the only existing gate of the original five similar gates.

See Catedral Basilica de San Juan Bautista

  • Location: 151 Calle del Cristo / Hours: Daily 9 am to 5 pm

The historic Catedral Basilica de San Juan, or San Juan Cathedral, is one of the oldest structures in Old San Juan and the oldest church built on US land. A hurricane destroyed the initial wooden building with a thatched roof, so in the 1540s, a more robust church replaced it.

When travelers arrived in San Juan, they passed through the San Juan Gate and into the cathedral to give thanks for their safe arrival.

While complimentary to enter, the church appreciates donations to help pay for restoration work. San Juan cathedral is still operational, and if you’re lucky, you can enjoy a service when visiting.

Stain glass window in the San Juan Cathedral
Stained glass window in the San Juan Cathedral

The Roman Catholic church seen today is small, but its gothic-inspired facade is beautiful. The interior features beautiful Spanish architecture and its restored frescoes are exceptional. I particularly enjoyed the stained glass windows, Gothic domed ceiling, and resting place of Ponce de Leon.

Ponce de Leon was a Spanish explorer who served as Puerto Rico’s first governor. It’s also the resting place of the Roman martyr Carlos Manuel Rodriquez Santiago.

Pray For A Miracle At Capilla del Cristo

  • Location: 1 Calle del Cristo / Open: Tuesdays and religious days

Further down on Calle del Cristo and at the end of the street, a small 18th-century stone structure is the smallest chapel I have ever seen. Almost hidden from sight, most visitors would miss the simple one-story design of stone walls and tiny belfry.

It is said that centuries ago, a rider fell off his horse at this stop during the Festival of San Juan Bautista. While the horse did not survive, Baltazar Montanez did, and he later constructed this chapel to give thanks for his life.

Inside Capilla del Cristo, or Chapel of Christ the Savior, the small altar glistens in silver and gold and is adorned with oil paintings. Many people come here praying for their own miracles.

Capilla del Cristo
Capilla del Cristo

Next to the small chapel, is Parque de las Palomas. Its shaded cobblestone courtyard attracts a large gathering of pigeons and the park offers picturesque views of San Juan Bay.

See Casa Blanca

  • Location: 1 Calle San Sebastian / Open: Tues to Sun 8:30 am to 12 noon, and 1 pm to 4 pm

While Catedral Basilica de San Juan serves as Ponce de Leon resting place, Casa Blanca was his home. Constructed in 1521, the house consisted of just one room initially. Now expanded, a USD 5.00 tour tells each room’s history. Like Capilla del Cristo, Casa Blanca is off the beaten path and easy to miss.

It’s sad to learn since Ponce de Leon traveled a lot, he never lived here and died before completing the home. Nevertheless, his descendants enjoyed the residence for 250 years.

On the second floor, the views of the city and San Juan Bay are stunning. Outside, the beautiful gardens are accessible and do not require a fee.

Admire La Fortaleza

  • Location: 63 Calle Fortaleza / Hours: Mon to Fri 8:15 am to 3:30 pm

Built between 1530 and 1540, La Fortaleza, also known as El Palacio de Santa Catalina, was the initial fortification before El Morro. Not well constructed as a defensive structure, the city repurposed it into the Governor of Puerto Rico’s residence.

While the Governor’s home is not freely open to the public, half-hour complimentary tours are available Monday to Friday at selected times. Sign up for the free tour is on Fortaleza Street, to the left of the entrance.

La Fortaleza in Old San Juan
La Fortaleza, the Governor’s home

Inside the beautiful mansion, the home has become a stately piece of colonial architecture with crystal chandeliers, period furniture, and fine artwork. The staircase is a show-stopper with Catalonian tiles and a domed ceiling featuring military trophies and shields.

The tour can include the dungeons, chapel, and surrounding gardens. Outside, the home has had a facelift with its baby blue color.

See A Narrow House

  • Location: 101 Calle Tetuan / Hours: Mon to Fri reservations are required for tours between 4 pm and 6 pm

From the outside, La Casa Estrecha appears too small to be a residential home. At five feet three inches wide at its widest point, it wouldn’t meet building codes in most metropolitan cities.

La Casa Estrecha is in the Guinness Book of World Records as being the narrowest two-story house in the Western Hemisphere. Wedged between two homes, what was once an alley, is now a narrow house.

Its current owner, architect Antonio Alvarez, designed the interior visitors see today. With a bright yellow façade and leaf-green doors, the house is hard to miss on Tetuan Street.

Inside, the home features chairs for lounging, a dining table for two, and a tiny kitchen at the end. Upstairs contains a sleeping area and bathroom similar to an RV washroom. On the upper level, views of the surrounding city are magnificent.

Relax At Balneario El Escambron

  • Location: Access off Calle San Agustin
Condado Beach, Puerto Rico
Condado Beach, Puerto Rico

If you’re more into sandy beaches, Balneario El Escambron, a Blue Flag beach offers excellent snorkeling around nearby coral reefs. Located just 2.3 km (1.4 miles) from the cruise terminal, a taxi ride is recommended. The beach’s calm, protected waters make it safe for swimming.

Despite its downtown location, it remains relatively quiet. From the warm waters, you can enjoy views of the stunning El Morro.

For more beach options, visit Condado, Ocean Park, or Pine Grove. These beaches offer beautiful white sands but have stronger currents due to less protection.

Experiencing Puerto Rican Food

I tried the local cuisine and signature drinks at Punto de Vista, a rooftop restaurant in the Milano Hotel, on a local’s recommendation.

The fifth-floor eatery, close to the cruise terminal, was hard to spot on my own. Simple decor and indoor/outdoor seating made it welcoming. Unfortunately, the elevator was out, so the climb worked up my appetite.

Mofongo, a classic Puerto Rican dish
Mofongo, a classic Puerto Rican dish

I ordered Mofongo Relleno, Pechuga de Pollo, and Mojitos. The mofongo was delicious, the chicken a bit dry, and the drinks strong—though I’m not much of a drinker.

Foodies should consider a tour to sample authentic Puerto Rican flavors across several spots.

Walk The Cobblestone Streets

Old San Juan invites exploration on foot, with charming cobblestone streets and pastel-painted historic buildings. Many streets showcase beautiful homes with intricate iron railings and unique wooden doors, details often missing in modern architecture.

Don’t miss Calle Fortaleza for shops and restaurants, plus Calle del Cristo and Calle San Francisco. Old San Juan Casino, a beautiful event space, has no gambling despite its name.

Colorful buildings of Old San Juan
Colorful buildings of Old San Juan

La Rogativa statue, near the San Juan gate, commemorates British arrival, showing a bishop leading torchbearers. On Calle de Cristo, Plaza del Quinto Centenario features El Tótem Telúrico, a 40-foot sculpture honoring Columbus’s arrival.

Old San Juan Shopping

For duty-free shopping in Puerto Rico, skip the usual brands and explore local goods. Puerto Rican coffee, with its rich aroma and bold flavor, is a top pick. Try brands like Volcanica, Alto Grande, Julian Coffee, and Yaucono. Puerto Rican rum is also a must-buy, offering unique flavors.

Rather than trinkets, I stock up on cooking staples. Puerto Rican spices, like Sofrito, Sazon, and Adobo, add authentic flavor to dishes.

As a fiber artist, I loved discovering San Juan’s famous bobbin lace, Mundillo—a delicate craft used to adorn tablecloths, napkins, and clothing.

Segway Tour Of Old San Juan

  • Location: Pier 2, Office 4, off Calle Marina

If walking in the heat isn’t for you, try a guided Segway tour. Segways are easy-to-ride and come with a quick lesson, offering a fast, safe way to explore historic hills and streets. A two-hour tour covers top spots, with a guide explaining Puerto Rico’s history from Spanish colony to U.S. territory.

I enjoy Segway tours for their small group size, making it feel like a personal history lesson. The tour meets at pier two on Calle Marina, near the cruise terminal. Helmets are mandatory (provided), and lockers are available. Bring a phone pouch or GoPro to capture the adventure.

Wrap It Up

Puerto Rico offers more than beaches; it’s a living history book. With just a day in Old San Juan, most sights are within walking distance.

Comfortable shoes and water are essential, as attractions typically close by 5 or 6 pm, limiting options for late-arriving cruise passengers. For an early start in San Juan, choose a cruise that docks in the morning or consider a Puerto Rico homeport cruise with extra land days.

Outside Old San Juan, renting a car allows access to El Yunque National Forest, the U.S.’s only tropical rainforest, with waterfalls, lush foliage, and scenic hikes.

Old San Juan is a UNESCO World Heritage Site with spectacular historical buildings and two fantastic forts. Visit El Morro or San Cristobal, see the San Juan Gate, and walk the beautiful cobblestone streets lined with colorful buildings.
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