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Old San Juan Walking Tour Tips

Old San Juan tour
Trees, vendors and cobblestone streets are common in Old San Juan

Two walking tours of Old San Juan spread 10 years apart convince me that the experience is all about timing.

The first tour was about places to see. The second was about people to see.

Both tours took place because we were taking Caribbean cruises that disembarked from San Juan. The city has two cruise port facilities. The largest is right by Old San Juan and offers easy walking access to the historic area. The smaller Pan-American Pier is about one mile away and requires either a taxi ride or much more walking.

San Juan is a major starting point for many cruises, especially ones that go to the western and southern Caribbean.

If a flight arrives in the early morning or the night before and the cruise leaves late afternoon, like many do, then visitors will have time to visit Old San Juan.

Visitors can easily tour Old San Juan on their own will a little planning. Otherwise, they can take a shore excursion by booking one either through the cruise line or directly with an operator. Prices start at about $55; prices depend on length and amenities.

Places to See in Old San Juan

The biggest attraction is the San Juan National Historic Site, the location of the fortress Castillo San Felipe del Morro and the smaller San Cristobal fort. They are at the tip of the peninsula about a mile from the terminal. Because of their location, anyone walking from the cruise terminal will walk through Old San Juan to reach them.

Allow 20 minutes to walk to the historic site and at least an hour for a quick tour of it. So anyone with at least two free hours can get a taste of both the old city and the historic site. If nothing else, a simple walking tour of Old San Juan offers many pleasant views of the historic area and plenty of chances for vacation photos.

For us at least, walking through the area and taking plenty of photos was just as enjoyable as touring the various historic attractions.

Visitors should check their luggage as early as possible at the terminal and walk or drive over to the historic city.

Old San Juan street
Old San Juan street; © Caribeez

Our first visit to the city focused on interesting places to see.

One of the attractions located closest to the terminal is the Cathedral of San Juan Bautista. It is the second oldest cathedral in North America, first built in 1521, destroyed by a hurricane and replaced with the current structure in 1540.

Casa Blanca, 1 Cll San Sebastian, is known as the White House. It was the residence of the descendants of Juan Ponce de Leon, the first governor of Puerto Rico, for more than 250 years. Ponce de Leon is most famous for his fruitless and eventually deadly search for the fountain of youth in Florida. Casa Blanca is now a museum about 16th and 17th century family life.

The nearby Museo de las Américas on Calle Beneficencia is a historic building with exhibits about history and culture in the Americas.

Another highlight is La Fortaleza, a grand structure also built in the 1500s. It is the oldest governor’s mansion in the Western Hemisphere still in use.

The most popular attractions of course are the impressive forts of San Cristobal and especially El Morro, built in the 1500s.

El Morro stands more than 140 feet over the sea and has dungeons, secret passageways and massive walls. Although both forts are worth a visit, anyone with limited time should go to El Morro and skip San Cristobal.

Old San Juan Comes Alive at Night

5 Things to Do in Old San Juan

  1. San Cristobal and El Morro forts
  2. Shop along cobblestone streets
  3. Casa Blanca
  4. La Fortaleza
  5. Plaza de la Darsena

Our second tour of the city was all about the people and the atmosphere of the “real” Old San Juan.

Yes, there any many interesting historical sites, lovely cobblestone streets and enough shopping on street after street to exhaust the most intrepid shopper. We had a longer visit this time and spent most of the day in shops or sharing a casual meal at one of the many plazas scattered throughout the city.

But Old San Juan comes alive with the people who live there on a Saturday evening in July. Once the shops closed at 5 o’clock, most of the tourists left the area.

We found ourselves wandering back down toward the water. We had a sense that locals were going there.

The traffic and walkers became heavier. We came out of the tight, curvy streets onto Plaza de la Darsena.

There we found a free public band concert with hundreds of local residents standing or sitting on steps and portable chairs. Pushcart vendors dotted the sidewalks.

As we wandered through the smiling, talking and listening crowd, we found ourselves on Paseo de la Princesa, a tree-lined boulevard with casually walking locals, many more vendors and the beginning of the historical Old San Juan city wall at El Morro.

The sun was starting to set in the distance over the end of the boulevard. More than coincidentally, we saw it setting over the bronze sculptures of Raices Fountain, which spray water dozens of feet into the air from the massive statue of people and animals.

Beyond the fountain, we walked along Paseo del Morro, the path between the city wall and the Caribbean. Trees hung over the path and lights started to sparkle as the sun set.

An Old San Juan tour is worthwhile for anyone stopping over on a cruise visit or embarking from San Juan. Going there in the evening is just as much fun as going there in the daytime.

Scott S. Bateman is a professional journalist who has traveled widely throughout the Caribbean and the Americas. He is the author of four books about cruising in the Caribbean, Alaska and Mexican Riviera.
September 08, 2022

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