Hitlist: How to spend a week in San Juan, Puerto Rico

El Morro in San Juan Puerto Rico

What do you think of when you hear Puerto Rico? Surfing? Spanish language? Ricky Martin?

None of those things is wrong, but our summer vacation to Puerto Rico was a wonderful lesson in the massive richness this little island has to offer. The hospitality is out of this world, the beaches are gorgeous, the adventures are breathtaking, and the food will leave you trying not to drool.

Below is a high level view of everything we had the pleasure of experiencing during our time on the island. TL;DR: go to Puerto Rico. You won’t regret it!

Where we stayed:

Map of Isla Verde vs. Old San Juan In Villamar, about two blocks from Playa Carolina. We rented through HomeAway, and I’ll admit I was skeptical about our location at first. Of course, everything turned out for the best – we were only about two blocks away from Playa Carolina, a lovely (not-too-packed) beach, and about a 20-minute taxi ride from Old San Juan. Puerto Rico definitely isn’t resort-centric like many of the other islands, and where we stayed felt pleasantly like we were entrenched in local, day-to-day culture.
That said, I’d probably vote to stay more centrally in Old San Juan next time we visit, simply because we’d have regular access to more walkable, historic, scenic areas.

Top 3 favorite excursions:

  • Rainforest hike with Ecoquest Adventures & Tours – Imagine hiking through a tropical forest. Now, imagine actually hiking up a very shallow riverbed that winds through a tropical forest. Also, imagine a little bit of rock climbing and other badassery with the aid of three very adept guides. That was our day in El Yunque rainforest. We started off with a safety course, then jumped right in to hiking up a riverbed. Our hike ended at a gorge where the water was untainted enough to drink straight from the river. We moved on to fantastic zip lining tour that had everyone yelling and laughing like crazy. And finally, we wrapped up with a homemade meal on the mountain. This trip isn’t for the faint of heart, but if you love a solid adventure, put this on the list. Read more about our rainforest hike.
  • Snorkeling and kayaking in Culebra with Kayaking Puerto Rico – Not to brag, or anything, but I’ve actually snorkeled with sea turtles, coral, and jellyfish. In aquamarine water so clear you can see straight to the bottom. The amount of time and effort it took to get to Culebra is so beyond worth it that I don’t even have the words. The guides were amazing, the scenery was absolutely breath-taking, and (come on!) sea turtles. Read more here!
  • Food tour in Old San Juan with Flavors of San Juan – This was one of the few non-outdoorsy things we did (in that we could actually wear sandals and normal clothes), and it was amazing. The food culture in Puerto Rico is beyond amazing, having been influenced and enriched by so many other cultures over the past several hundred years. This particular tour was fantastic. We got to sample a huge variety of local cuisine (locally made popsicles, mallorca bread, flan, piña coladas, etc.). And we also got great taste of local history as our guide walked us through the winding streets of Old San Juan. This one is a must-do for any visitor.
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Top 3 essential places to eat:

  • España – This wonderful neighborhood eatery became our home base. We walked here for breakfast, used it as a landmark for any taxis we ordered, and often ended our nights with a pastry from one of their well-stocked cases. The staff were amazingly helpful. They’d let me try to speak my admittedly rusty Spanish, and were always patient but ready to make menu recommendations. One of my best memories from our entire trip was ending a night here. As we all shopped indecisively for pastries, an older gentleman (an obvious regular) stood up and said, “You HAVE to try quesitos! If you don’t like, or even if you do, I pay!” Let me tell you: quesitos are cream cheese pastries, and they are AMAZING. Do yourself a favor and make a trip to España!
  • Rosa de Triana – This was one of many stops along our food tour. The building itself is memorable due to its rounded walls and ceilings (they do explain the historical significance). But the best part of our visit was being able to mash and mix our own mofongo, while enjoying some pretty tasty sangria and other local foods. After a long morning of walking around Old San Juan, this is exactly the place you want to stop for munchies and a drink!
  • Aromas Coffeehouse and Restaurant – Fun fact: Ricky Martin’s family owns this coffee shop, and his cousin definitely took great care of us. Their mallorca y jamón sandwich was out of this world, and everyone’s cafe con leche had its own little art. The ambiance of the coffee shop is lovely. With gentle lighting and not much in the way of climate control, it feels intimate and cozy, and the warm breeze wafting through makes each bite a little better. 100% can’t wait to come back here.
  • Bonus! Triana Tapas y Flamenco – Disclaimer: this is not the most amazing food you’ll have in Puerto Rico. But the music and the show completely *make* this experience. Juan Carlos, a fabulous flamenco guitarist (with quite a pedigree!), has a show that will dazzle you with lovely dancers and jaw-dropping musical skill. Definitely worth a stop if you’re in the Old San Juan area.
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Top 3 things to see and do:

  • Buy a custom Panama hat – As we wandered around Old San Juan on one of our last days on the island, we came across Olé Curiosidades, a small shop on Fortaleza St. that’s full to the brim (no pun intended!) of Panama hats. The owner, Guillermo, and his colleague gave us a history lesson of the Panama hat, and walked us through the process of customizing and fitting every part of it. Then, as we were ringing out, Guillermo laughed and tossed a couple of huge vintage postcards into my bag. The experience was so memorable (and the hat was so cool) that Luke is STILL kicking himself for not getting one, too!
  • Take in the history – One of the best things about Old San Juan is that it’s one of the oldest walled cities in the New World. Even better, quite a lot of that infrastructure has been amazingly well-preserved. Visit El Morro to get a feel for the island’s early sea defenses. Walk the blue-stone streets near the governor’s mansion. Take in the soaring beauty of the Cathedral of San Juan Bautista (incidentally, right across from Rosa de Triana). And don’t forget to admire the gate: the entrance to the city that every pilgrim, every immigrant, every arrival used to walk through.
  • BASK – We enjoyed every part of this trip (except perhaps the crazy taxi drivers). But some of the more memorable moments involve simply being lazy on a beach. Take the time to get acquainted with the island. But also take advantage of your delicious time in the tropics to get a little reacquainted with yourself.

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