Exploring the Streets of Old San Juan with Kids in Tow

I’m not gonna lie, our reasoning for traveling to Puerto Rico was three fold.

  1. Flights were cheap
  2. We are SO ready for warm weather
  3. It’s one of the most colorful places around**

I’m a go-go-go type of traveler. You won’t catch me flying across the country just to read a book by the beach, no no. I like to engross myself in the culture, eat all of the local cuisine, and find at least one adventure.

colorful streets of Old San Juan Puerto Rico

So when I read San Juan itineraries that included a full day of exploring Old San Juan, I was worried. “And do what?”

I underestimated it, no doubt. With camera in hand and those colorful buildings I expected, I could spend more than just one day in beautiful Old San Juan.

Traveling and exploring the colorful streets of Old San Juan, Puerto Rico with kids

The Hotel

We’re loyal Starwood Hotel guests (also: point collectors), and there are four Starwood Hotels in Puerto Rico. Mark was leaning toward The St. Regis at first–though I’d like to visit one of the hotels that fall under that name, I’m just not a fan of staying in resorts outside of the states. We have beautiful beaches in the U.S., and resorts, to me, only replicate the luxuries of American life, keeping guests in a bubble while disallowing the local economy to develop as a result of the increased tourism. I just don’t think that’s cool.

So, we picked a cheaper hotel, closer to colorful streets and delicious eats: The Sheraton Old San Juan. We roomed in a suite that had a balcony with views of Bahía de San Juan and a door between T in the living room and us in the bedroom. (Something we always try for, but some suites are not as private.)

View from our suite at the Sheraton Old San Juan

The best picture of me from the trip was taken by Tobias in this horrible lighting and a wrinkly skirt. Always behind the camera, never in front!

The Streets

The buildings of Old San Juan are picture perfect examples of Spanish Colonial Architecture: simplified, flat-roofed structures with ornate details, like wrought iron balconies, that were imported from Spain.

Resting in Old San Juan Puerto Rico 1Historical Old San JuanEverything is so colorful in Old San Juan, Puerto Rico!Old San Juan, one of the most colorful places in the worldColorful Streets of Old San Juan, Puerto RicoTraveling with children in Old San Juan, Puerto RicoExploring the colorful streets of Viejo San Juan, Puerto RicoOld San Juan, one of the most colorful places in the world

It’s so crazy to think that at one point, these beautiful buildings were nearly destroyed.

Travelling to Puerto Rico with Kids

“So, the streets are pretty and all, but, are they safe? And for KIDS?”

A few days before we left for the island, M’s coworker, who is Puertorriqueña, suggested many places to see and eat (he took more interest in the latter, of course) and warned us of the dangers. Puerto Rico holds a reputation of having the most murders of any U.S. state or territory, due mostly to the drug trade in the Caribbean, but also–it’s poverty stricken and densely populated. Those are the first ingredients for crime in any part of the world.

Street Art in Old San Juan, Puerto RicoWe were only in the most tourist dense parts of PR for the entirety of our brief trip, we stayed away from the areas the internet warned us about, and we were safely tucked into the hotel before night fell–with all this walking, kids get tired! Don’t be afraid to visit Puerto Rico because of the crime rate, but do be afraid to have anything to do with the drug trade anywhere (duh) and do take precautions.

The Headwear

We had several people suggest that we go to Ole Curiosidades to buy some authentic Panama hats at the only full-service hat shop on the island. Mark has a new found obsession with hats in general, so we had to make this our first stop.

Ole Curiosidades in Old San Juan, Puerto RicoSouvenirs from Ole Curiosidades in Old San Juan, Puerto Rico

We all love our hats!

Panama hats at Ole Curiosidades in Old San Juan, Puerto Rico

The Fort

At the edge of Old San Juan, you’ll find a gorgeous park, a National Historical Site,  and UNESCO World Heritage  site: Castillo San Felipe del Morro, which I wrote all about on yesterday’s post.

Use the subscribe button on the right hand side of the screen, and tune in for following posts where I write about great places to eat in Old San Juan and trying to take my afraid-of-heights seven year old ziplining in Puerto Rico.
**I’ve become captivated by this list of colorful places to travel to. I’ve been to a few, may never go to most, but to get a better idea of where they are in the world I made a map of the world’s most colorful places on Google.
TinyKelsie Exploring the colorful streets of Old San Juan, Puerto RicoOld San Juan Puerto Rico safe to explore with kids

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5 thoughts on “Exploring the Streets of Old San Juan with Kids in Tow

  1. Ahhh, I love San Juan! Your pictures make me want to return. I have only been as a single woman in my 20s. I have not yet gone with my child, and despite the crime rate, I never felt anything but safe there.

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