I’ve been to Puerto Rico twice. But the first time I wore my Lollapalooza T-shirt the entire time and had my nose buried in my required Norton Anthology reading for my college literature class. That’s how I rolled in the 90s as a 19-year-old traveling with my parents on a break from college. So I am not sure that visit “counts.” (For the record, I am in no way apologizing for that T-shirt or its frequent use.)
But I had the opportunity to go back, years later, as an adult in charge of my own time and itinerary. Mr. Family Trip was sent to San Juan on a business trip, so I joined. We fell in love with this Caribbean island.
Today, Puerto Rico is trending as a destination. And it’s no wonder why. Airline tickets are inexpensive (especially compared to other islands). Entry for Americans is easy – no passport required for Americans. And Puerto Rico uses the U.S. dollar.Â
Puerto Rico is actually a string of islands, but the easiest place to go for a quick weekend getaway (as we did) is San Juan.
With a weekend in Old San Juan, combined with a kayaking tour in Fajardo, we experienced everything a good vacation in the sun has to offer: history, culture, beautiful views, and sand.
It seems as though this once-often-overlooked destination is hot right now. And I am excited to see that!
Of course, with Puerto Rico, it has also seen trauma that should be held. It’s experienced earthquakes, hurricanes, crime, and political tension as it considers its relationship with America. As it grows and becomes more powerful, it is changing. Yet while tourists flock to dance and drink mojitos, it is worth remembering that people’s lives happen here.
Old San Juan is more touristy than ever, yet also safe and the infrastructure creates easy pathways for enjoyment. New businesses are springing up to meet the new demand. And as the old is decimated by natural disasters, the resilience of the people creates new opportunities and visions.
Puerto Rico is a dynamic place.
Here are Our Top 5 Things to do for a Weekend in Puerto Rico:
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Visit Santa Maria Magdalena De Pazzis Cemetery
Visiting a cemetery is not as macabre as it sounds. This particular cemetery, located in Old San Juan, is visually stunning and a place that demands reverence. It was founded in 1863, and the white-washed stones against the Caribbean sea blue makes you think through what heaven looks like.
Cemeteries such as this have a steep and rich history in the Catholic church. A walk through here is a walk through both the past as well as the future that exists after we, too, pass on.
A visit here is sacred and memorable.
If the dead can hear, then we can't imagine a better place to be with the constant sounds of ocean waves, the whistling of the trade winds, and the laughter of children running on the grounds of El Morro flying kites.
For more on the Santa Maria Magdalena de Pazzis Cemetery, visit: sanjuanpuertorico.com/santa-maria-magdalena-de-pazzis-cemetery
Enjoy the Streets and Nightlife of Old San Juan
We thoroughly enjoyed wandering the streets of Old San Juan. We stayed pretty tight in the historic, tourist-friendly area, but found so much fun.
The place was vibrant both during the morning hours, with brightly painted building fronts and the sea peeping through, and during the late night hours where music and laughter poured out of the open doors and windows into the streets.
What to eat? Mofongo!
Where to start your night of dancing? La Placita!
Paddle the Bio Bay in Fajardo (at night)
We rented a car and drove out to Fajardo, where we did a guided kayak tour of the Bio Bay.
While we’ve kayaked the bioluminescent bay in Grand Cayman, the trip in Puerto Rico felt particularly magical. In Puerto Rico, we kayaked in the dark through hushed mangroves. We spit out into a large bay that was devoid of any ambient light as, unlike Grand Cayman, there wasn’t a smash of development and large houses on the bay.
Also, when we did our tour in Puerto Rico, swimming in Bio Bay was prohibited. I am not sure if that’s changed but given the fragility of our earth, it felt like the right decision and far more comfortable than the more free-for-all we experienced in Grand Cayman.
Definitely take a tour with a tour guide to fully enjoy this.
Visit Castillo San Felipe del Morro
As I’ve shared before, we have come to love UNESCO world heritage sites and appreciate the designation more and more as we see the world. This spot is no exception. This old fort is rough and elegant, sitting on the shores of the island.
Dating back to the 16th century, it has protected and defended Puerto Rico for centuries.
For more on Castillo San Felipe Del Morro, visit: www.nps.gov/saju/planyourvisit/index.htm
Hit the Beach and Bask in the Sun
Puerto Rico has beautiful beaches, and they are free and open to the public! While the ones in San Juan can be crowded, it is fairly easy to drive to more remote beaches if you have a car.
Many resorts now are catering to guests who want the tropical experience, with beach chairs, pools, and ocean views. We enjoyed sunning and al fresco lunches where the breeze rustled our hair.
Want a list of the best beaches? Check out this post.
As you consider family plans and travel this year, why not add this gem of an island? However, maybe leave the Lollapalooza T-shirt at home and pack an extra swim suit instead.