A Walking Tour of Old San Juan

01 of 08


Old San Juan Puerto Rico
David Madison / Getty Images

Walking around Old San Juan is the best way to immerse yourself in its timeless beauty and charm. Even the most determined tourist can't cover all there is to see and do here in one day; among the more celebrated monuments and memorials are countless small wonders that will tempt the historian, the shopper, the diner, and the curious child in you.

This walking tour covers the major points of interest, focusing on the historic buildings that make up the character of the old city. How long the tour takes will depend on how much time you want to devote to each stop, but you should be able to cover it all in one day. If you don't want to walk, there are free trolleys that you can pick up at various points in the city that cover all of these stops. But I'd recommend hitting the streets.

Before you get going, make sure you have:

  • A hat, sunblock, and water: the Caribbean sun can be merciless, especially in the summer, and you'll want to be shaded and hydrated.
  • Comfortable walking shoes: you'll be covering a lot of territory, some of it along steep inclines, much of it on cobblestone streets.
  • Your camera and plenty of batteries and film, if you use film.
  • A map: if you don't have one already, you can pick one up at the tour's starting point.

We begin our tour at the Plaza de la Dársena, at the foot of the city. Why here? Two reasons: one, if you're coming off a cruise ship, the plaza is on your left as you make your way into the city. And two, this is where you'll find the La Casita Tourism Information Center, where you can pick up maps and other useful information. From here, you'll head towards your first stop: the imposing Castillo de San Cristóbal.

02 of 08

First Stop: Castillo de San Cristóbal

Fort San Cristóbal
fortherock / Flickr / CC BY-SA 2.0

From the Tourism Information Center, head east along Comercio Street, passing by the piers. (If you want a little pick-me-up to get the blood circulating, stop by Casa Don Q, across the street from Pier 1, for a free sample of Don Q rum!) Follow the road as it curves north into the city and becomes O'Donnell Street. You'll pass by the historic Tapia Theater and then arrive at Plaza Colón, instantly recognizable for its white marble pillar atop which stands a statue of Columbus. Crossing the plaza, you'll be on San Francisco Street. Take a right here and follow the road to the end, and turn left onto Norzagaray Street. The Castle looms on your right, and the entrance is just ahead.


  • Castillo de San Cristóbal, or Saint Christopher Castle, is the largest fort in Puerto Rico, and the largest fortification built by the Spanish in the Western Hemisphere.
  • Completed in 1785, it covers 27 acres of land and rises almost 150 feet above sea level.
  • Built to guard against a land assault from the east, San Cristóbal is an example of the “defense-in-depth” architectural model. This was a tiered network of fortifications that would force an enemy to face several defensive barriers before the fort was breached.
  • San Cristóbal fired the first shot of the Spanish-American War in 1898.
  • In 1942, the U.S. army built World War II bunkers on the northern face of the fort.
  • From its ramparts, you can see beautiful views of El Morro, the city, and the piers.
03 of 08

Second Stop: El Morro

Lighthouse at El Morro
Glasshouse Images / Getty Images

From Castillo de San Cristóbal, you can continue up Norzagaray Street, which takes you directly to El Morro. However, this is a relatively uninteresting route, despite the beautiful views of the water on your right. If you want to walk through the city, turn into Sol Street from Norzagaray and walk west for several blocks until you get to Cruz Street. Take a right on Cruz, and meet up with Norzagaray again, just before the San Juan Museum. You can take a quick detour here (the museum is not very large) or keep going until you get to the castle. Look to your left as you approach the castle and you'll see a large open space with fountains and a tall, clay pillar. This is the Plaza del Quinto Centenario.


  • El Morro's official name is the Castillo de San Felipe del Morro; while it is often called a "fort," there are actually no forts in Old San Juan. They were designated as castles and later mistakenly identified as forts by the U.S. government.
  • In over 400 years, El Morro has withstood countless attacks and has never been defeated by sea. It was only taken once, in 1598, in a land attack led by the Earl of Cumberland; it was this attack that prompted the construction of the Castillo de San Cristóbal.
  • Step inside one of El Morro's Garitas, or sentry boxes, for a unique photo moment; these domed structures have become symbolic icons of Puerto Rico.
  • At one point in El Morro's history, the U.S. Navy converted the large lawn leading up to the fort into a golf course. Today, people come here to picnic and fly kites.
  • El Morro means "The Promontory," and this fort juts out into the entrance of the San Juan Bay; look across the water at El Cañuelo, another, smaller fort that helped El Morro guard the entrance to the bay.
  • The fort is divided into six levels and includes dungeons, barracks, passageways, and storerooms.
04 of 08

Third Stop: El Cuartel de Ballajá

Ballajá Barracks
Gary Conner / Getty Images

From El Morro, walk back across the lawn, cross Norzagaray Street, and you'll find yourself facing the Cuartel de Ballajá.


  • The Cuartel de Ballajá, or "Ballajá Barracks," housed Spanish troops during the 1800s, and later was the quarters for American soldiers following the Spanish-American War.
  • The building was used as a military hospital during World War II.
  • Now, the second floor of barracks has been devoted to the Museo de Las Americas, which has three permanent collections: the African Heritage, the Indian in America, and Popular Arts in America.
Continue to 5 of 8 below.
05 of 08

Fourth Stop: La Casa Blanca

casa blanca puerto rico
James Byrum / Flickr / CC BY-ND 2.0

From the Cuartel de Ballajá, cross the Plaza de Beneficiencia (there is a beautiful sculpture here of Eugenio de María de Hostos, a noted educator born in Puerto Rico) to San Sebastián Street. Take a right and follow the street to the end, where you will find La Casa Blanca.


  • La Casa Blanca means "The White House," and in a way, it is; this was the home built by the Ponce de León family in 1521. It is one of the oldest remaining monuments in San Juan.
  • Contrary to popular belief, Juan Ponce de León never lived here, but his family occupied the house for 250 years.
  • La Casa Blanca also served as the first military structure on the island; built of stone, it was used as a fort during Puerto Rico's infancy.
  • Today, it is a museum that chronicles the life of modern Puerto Rico's founding family.
  • A guided tour takes visitors through the main rooms of the house, where original and recreated period furniture help to capture the spirit of life on the island during the 16th Century.
06 of 08

Fifth Stop: La Fortaleza

La Fortaleza

Zain Deane

Walk east along San Sebastián Street until you get to Cristo Street. Turn right on Cristo and take your time walking down one of Old San Juan's busiest and most picturesque streets. You'll probably be hungry by now, and this is a good time to stop for lunch; there are plenty of restaurants on Cristo Street.

As you head south, you'll pass many landmarks. The lovely El Convento Hotel will be on your right, and directly across from it is La Catedral de San Juan, the largest and most revered Cathedral on the island. You can take a quick self-guided tour inside and see the remains of Ponce de León atop a marble tomb. Continue down the road until you get to Fortaleza Street. A short distance away, you'll see La Capilla del Cristo, a chapel built to memorialize a local legend. Turn right at Fortaleza Street and walk to the end of the road to La Fortaleza.


  • Completed in 1540, La Fortaleza is the oldest governor’s mansion in the western hemisphere and has housed 170 governors of Puerto Rico. It was also the island's first true fortress.
  • In another case of double identity, La Fortaleza, which means "The Fortress," also goes by the name of Palacio de Santa Catalina, or "Santa Catalina Palace."
  • Its distinctive blue-and-white façade was not completed until 1846 when it became the exclusive residence of the governors.
  • Guided tours take you through the sumptuous interior, with gilded banquet halls, galleries, and rooms furnished in the style of the period.
  • One of the best things to see in the mansion is a broken, old mahogany clock that stands in a corridor. Just before relinquishing the building (and the island), the last Spanish governor paused in front of this clock and struck its face with his sword, stopping time to note the very last moment of Spanish rule in Puerto Rico.
07 of 08

Sixth Stop: La Rogativa

La Rogativa Statue Of Old San Juan Details
Paul Downey / EyeEm / Getty Images

When you exit La Fortaleza, take a left and follow the road as turns west. You're now on Recinto Oeste Street. Keep walking along this road. You'll pass by the San Juan Gate, the last remaining gate out of the original five that once marked the only passages into the walled city. Continue heading north until you get to Caleta Las Monjas. Take a left and you'll see the Plazuela de La Rogativa straight ahead.


  • La Rogativa means "The Procession," and the sculpture shows a procession of faithful Catholics holding torches and crosses aloft.
  • It is known that the procession took place in 1797, an act of faith during an invasion of Puerto Rico by the British. However, the legend goes that Sir Ralph Abercrombie, seeing the figures in the distance and believing they were Spanish reinforcements, gave up the attack.
  • Look out across the water for a beautiful view of the city wall and La Fortaleza.
08 of 08

Final Stop: The Raíces Fountain

Raices fountain
Brad Clinesmith / Flickr / CC BY-SA 2.0

If you've timed this tour just right, it will be close to sunset by the time you leave La Rogativa. Retrace your steps down Recinto Oeste Street and walk through the San Juan Gate. You're now on the Paseo del Morro, a winding path that hugs the city wall and snakes around the city. Take a left and enjoy the stroll, with the water on one side and the mighty walls on your left. The road leads you directly to the magnificent Raíces Fountain, one of the most romantic spots in Old San Juan.


  • The Raíces, or "Roots," Fountain celebrates Puerto Rico's Taíno, Spanish, and African heritage.
  • The fountain is lovely during the day when you can see little children dancing amid its spouts of water, but breathtaking in the evening, as the sun sets behind it. It makes for a fitting conclusion to the tour.
  • Continue walking along the Paseo La Princesa (there are stalls and vendors selling snacks and souvenirs along the way), which will lead you back to Plaza de la Dársena.
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