Exploring Old San Juan

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I had so many collaborations and blogging work to catch up on when I got back from vacation that I’m only getting around to sharing my Puerto Rico content now! I felt so inspired there—something about the warm weather and being by the ocean just makes my heart happy. We spent our first couple of days in San Juan, the capital city. Old San Juan is the part of the city that dates back to the 16th century, with the original city walls as a perimeter connecting the Spanish San Felipe del Morro and San Cristóbal fortresses. A popular cruise stop, Old San Juan is known for its brightly colored buildings, cobbled streets, roaming cats, and old-world charm.


For those of you who don’t know, Puerto Rico is a territory of the United States, which as a tourist means you don’t need a passport to visit and you can use American money. It’s a complicated relationship, and the topic of Puerto Rican independence is a hotly debated one. This year’s Law and Society Association (LSA) annual conference is being held in San Juan and is all about how U.S. territories are “separate and unequal”. It’s a really interesting issue, and you can read more about it on the LSA’s website here. I would have loved to attend the conference, which is in June, but I bought my tickets to PR before I knew about it! Damn—could’ve killed two birds with one stone.

If you’re interested in some of the history of Puerto Rico and its Spanish colonialist past, this brief History.com article provides a good overview of the island’s native Taíno population, the Spanish conquest, and Puerto Rico’s transfer to the U.S. government at the end of the Spanish-American War in the late 1800s.

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Okay, enough about the history, let’s talk about the outfit! I wore this adorable cobalt blue romper on our first day of exploring Old San Juan. It’s made out of a thick denim-like material and has pockets, puffy sleeves, and the cutest collar. I bought it at the local boutique fashion show my aunt and I attended a few weekends before the vacation. I wasn’t sure if I should buy it because of the length (I feel a little self-conscious in super short things), but my aunt convinced me I needed it… and I’m so glad she did! It’s such a cute piece and looked amazing among all the brightly colored buildings of Old San Juan.

I also appreciate that the romper has sleeves because my shoulders tend to burn really easily. I was worried the thick material would feel too hot (it was mid-80s the whole time we were there), but I actually felt quite comfortable! And the fabric hid any sweat marks, which was amazing.

I paired the romper with my light purple leopard sneakers from UIN Footwear. I knew we would be walking a ton, so I wanted to wear something ultra-comfy—these shoes quite fit the bill! I also wore big yellow earrings that I bought for the trip and carried my new Shop LC wicker purse. While it’s on the smaller side, it still fit my wallet, phone (just barely), a few bandaids, and a small tube of sunscreen—all the essentials.

I didn’t have a chance to wash this romper before wearing (which is rare for me—you should always wash clothes before you wear them out!), and the blue dye rubbed off on the strap of my purse, which is a bummer. I’m hoping I’ll be able to use stain remover, but if not, the blue isn’t that noticeable. This is just a friendly reminder that when you do wash a clothing item for the first time, always wash it by itself! You never know how the colors might bleed and don’t want to risk ruining any of your other clothes.

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Old San Juan is unbelievably picturesque. I took hundreds of photos while there! All of the colorful buildings, the plants, the kitty-cats, and of course the Atlantic Ocean make for photo-ops galore. We saw a handful of different artists set up on the sidewalks while there, painting watercolor scenes of the cobbled streets. You can find all sorts of beautiful artwork in the souvenir shops throughout Old San Juan. I found a few I liked but they were too big to fit in my suitcase… I figure I need to pick a photo I took and paint my own!

In a lot of ways, Old San Juan reminds me of a tropical version of the French Quarter in New Orleans. They both have a very similar style of architecture, and every now and again, if you’re lucky, you get a little whiff of vomit smell while wandering the corridors.

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What was so fun and different about this vacation was how relaxed it was. For the most part, I’m a planner—I like to visit a place and see and do as much as possible while there to make the long plane travel and expensive ticket worthwhile. That doesn’t mean I’m not up for a spontaneous adventure, but I definitely err towards the side of having an agenda each day.

There was no agenda for Puerto Rico. My dad and I made a list of a few things we knew we wanted to see while in Old San Juan and otherwise enjoyed where the day would take us. During our two days in the city, we would wake up, find a spot for breakfast or café con leche, and then wander, letting ourselves get distracted by souvenir shops, the closest piraguas stand (Puerto Rican shaved ice), or the smell of fresh seafood. I wouldn’t travel to just any city with no plan, but Old San Juan lends itself very well to exploring—there’s so much to stumble upon!

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I’ve been working on a more comprehensive travel guide for Puerto Rico, so consider today’s post just a teaser. I was so fortunate to have some of my extended Puerto Rican family join me on this vacation and give me the insider scoop on where to go, what to eat, and all that jazz! I hope to share it all with you in the coming weeks. Have a great start to your weekend!


Miles of smiles,


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