On a trip earlier this year to San Juan, Puerto Rico, I had only two days to see the most iconic sights in the city. I wanted to fit in as much as I could. To do that, we stayed in Old San Juan at the 352 Guest House Hotel Boutique. This way, we could walk to almost everything while getting the flavors of the old city.
Keep in mind that my “best things to do” list is tooled to a compressed time frame. Another day or two could result in more leisurely and more complete sightseeing.
Note: Even though Puerto Rico is part of the United States, not everyone speaks English. You can get by if you don’t speak Spanish but shouldn’t be surprised if a random stranger cannot answer your question in English.
Take a Walking Tour
Lately, I’ve tried to schedule a walking tour for my first day in a new city. It teaches me the layout of at least part of the city. In San Juan, our walking tour wound its way through Old San Juan as our guide detailed historical and cultural facts.
Old San Juan is such a colorful part of the city that exploring it feels downright cheerful no matter the time of year.
Visit San Juan Gate
La Puerta de San Juan
Like so much of Old San Juan, the San Juan Gate stands out for its bold color. The red gate is one of the original entrances to the walled city. It dates back to 1635 (yes, the city is that old) and stands 16 feet tall. You can see it from above, or you can walk down and walk through it. Keep in mind that the interior side is plain, although clearly constructed of ancient stone.
Explore Castillo San Cristóbal
San Juan is remarkable both for how old it is and for how well-preserved its history has remained. The Castillo San Cristóbal stands watch over both city and sea. The fortress has withstood centuries of attacks and occupations.
Take your time to explore the different levels and passageways.
Because of its position on the old wall, you can easily imagine how this fortress managed to protect the inhabitants from attack. Make sure you take in the views of both San Juan and the Atlantic Ocean.
Tour Castillo San Felipe del Morro
El Morro
About a mile from Castillo San Cristóbal lies Castillo San Felipe del Morro, also known as El Morro. The construction of El Morro began in 1539, but it didn’t reach its full imposing power until the 17th century. Because it overlooks San Juan’s harbor, its strategic placement is evident.
The U.S. National Parks Service manages the site. I love all the detailed descriptions of how the men stationed there defended it. The cannon tracks especially impressed me.
View a Historic Cemetery
Adjacent to El Morro but closer to sea level, you’ll find the impressive Santa Maria Magdalena de Pazzis Cemetery. The interred represent some of the most influential people in San Juan. To those of us unfamiliar with Puerto Rican dignitaries, the most notable graves are José and Miguel Ferrer.
Because we were short on time and because access seemed to be a long walk, we contented ourselves with looking at it from above.
Visit Cathedral of San Juan Bautista
The Cathedral of San Juan was first constructed in 1511, although it has undergone many phases of construction, up until 1905. The diocese has kept the cathedral in stellar condition. As our walking tour guide proudly told us, it is the second oldest church in all of the Americas. The cathedral houses the tomb of Juan Ponce de Leon.
Book a Rum Tasting
Puerto Rican rum is among the most famous in the world, thanks to centuries of making it., Despite that long history, San Juan has only a few small distilleries that offer rum tastings,. We booked one at Scryer Rum and Barrelhouse.
Although Scryer doesn’t distill its rum in Puerto Rico — it is distilled in the equally rum-famous island of Barbados — they barrel-age it in a small bar and storefront in Old San Juan.
We enjoyed the brief tour of how rum is made and what makes Scryer distinct. Of course, the tasting at the end convinced us to buy a bottle to take home.
Visit The White House
Museo Casa Blanca
The oldest residence in San Juan, built for the governor Juan Ponce de Léon, now houses a museum. As you walk through the rooms. you’ll learn about the history of the house and the details of its expansions over several periods.
Be sure to allow enough time to stroll through the landscaped grounds. The tropical climate of Puerto Rico enables year-round botanical interest.
Check out Capilla del Cristo
This tiny chapel, located next to the Parque de las Palomas and at the end of Calle del Cristo, was built in the 18th century and still endures today as a much-visited site. It has become an iconic symbol of Puerto Rico.
Eat Like the Locals
Puerto Rico has some local dishes that you can’t find on the U.S. Mainland unless you dine in a heavily Puerto Rican area. Thanks to the recommendation of our innkeeper, we ate at Casa Luna Rest., supposedly a favorite of locals who live in Old San Juan. We enjoyed mofongo, fried plantains, empanadas, and the server-recommended skirt steak.
The Verdict
We visited close to Christmas, and decorations abounded, but I’m sure that you can find a festive vibe any time of the year. I was surprised by the enduring structures that date back centuries, making Old San Juan an excellent destination for history buffs.
