I was tempted to include this post in my American Cities series, but it didn’t feel right. Puerto Rico was colonized by Spain in 1508 following Columbus’ arrival in 1493. It remained in Spanish hands until the US acquired it in 1898 following the Spanish-American War. In 1917, Puerto Ricans received US citizenship, but not much came with that. As an unincorporated territory, Puerto Ricans cannot vote for the President/Vice President, they have a non-voting representative in Congress, and typically don’t pay federal income tax. It’s a system that certainly doesn’t work for Puerto Rico.
In recent years, land has been bought up by Americans who don’t necessarily care about their impact on Puerto Rico. Housing prices are becoming more and more unaffordable. I don’t have all the answers, but I do believe that Puerto Ricans should be allowed to decide if they want statehood or independence and I believe it is the United State’s job to help them toward that goal as we have been their oppressors for over a century.
There’s so much history to learn and experience in Puerto Rico, and we wanted to spend a sizeable chunk of our time in San Juan, exploring the various neighborhoods. Our first day took us to Old San Juan. We had an Uber drop us off at the farthest tip: Castillo San Felipe del Morro.

Built to protect San Juan Bay’s harbor from attack by sea, this was the first good harbor for sailing ships en route to the “New World” after a one- or two-month Atlantic voyage from Europe. Construction began in 1539 and the mammoth fort now consists of six levels: Water battery, original tower, lower plaza, main firing battery, main plaza, and land defense.
What we didn’t know before we went was that when you buy an entrance ticket ($10), you also have access to Castillo San Cristóbal for the next 24 hours as well. Out of everything we saw in Old San Juan, El Morro is where we spent the most time. The fort is gorgeous, but also feels a bit sad. Likely, because it reminded us of time spent in previous forts like Cape Coast Castle in Ghana.
Unlike Cape Coast, El Morro wasn’t used as a large slave market, but, of course, slaves made their way through the fort just the same. Puerto Rico was original settled by Indigenous groups 2,000-4,000 years ago (the Ortoiroid, Saladoid, and Taíno). During Spanish colonization, there was an influx of African slaves and settlers from the Canary Islands and Andalusia.


Right next door to El Morro sits the Santa María Magdalena de Pazzis Cemetery (known simply as the Old San Juan Cemetery). It was established in the late 1800s and is the burial site of some of Puerto Rico’s most famous citizens.
The gates were closed when we walked by, but we still got stunning views from above.

Our end goal was Castillo San Cristóbal, but we had all of Old San Juan to weave our way through first. Unsurprisingly, I fell in love with all the colorful buildings. Also unsurprising: The difficulty of photographing those buildings! The streets are quite narrow and traffic is pretty steady.
We passed by the sites: Ballajá Barracks, San José Church, San Juan Cathedral, Christ Chapel, and Old City Hall. We popped into the stores – some chains, some privately owned. And visited a few of the restaurants. Our only real disappointment? We had arrived in Puerto Rico a bit under the weather and weren’t feeling well enough to drink. Which was too bad, because La Factoría and La Taberna Lúpulo were high on our list.



In 1898, the US declared it a felony for Puerto Rico to display its flag in public. Until 1952, the only flag permitted to be flown on the the island was the United States flag. When then governor, Luis Muñoz Marín, adopted the flag, the meaning of the colors were changed.
Originally, the red stripes represented the blood from the brave warriors, the white stripes represented the victory & peace they would have after gaining independence, the white star represented the island of Puerto Rico, the blue represented the sky & blue coastal waters, and the triangle represented the three branches of government.
Now that the flag was official, the white stripes stood for the republican form of government and the sky blue of the triangle was changed to dark blue to resemble the flag of the United States.
But on July 4, 2016, a group of women with the Artistas Solidarixs y en Resistencia (Artists in Solidarity and Resistance) repainted a popular door at 55 Calle San José in black and white. The purpose was to protest the Puerto Rico Oversight, Management, and Economic Stability Act. Signed into law by President Barack Obama, it has been criticized by some as being an act of colonialism.
Now, the black and white flag is seen as a symbol of Puerto Rican independence, resistance, and civil disobedience.

Finally, we ended our day at Castillo San Cristóbal. I wouldn’t recommend putting it off for the very end of the day – we noticed that parts of the fort were closed earlier than the official hours (9am-5pm), but luckily, we still had enough time to view everything.
While El Morro was built to protect the city from sea, San Cristóbal was Spain’s response to land attacks from England and the Netherlands. Construction began in 1634 and took over 150 years to complete. It is the biggest European fortification in the Americas.

Old San Juan isn’t the only neighborhood in San Juan and we knew we definitely wanted to spend some time out of the city as well. But wandering through Old San Juan really gave us a good understanding of the history of Puerto Rico.