If you're a huge fan of Mary Poppins, this post is also for you (read: feeding pigeons and flying kites are among the top activities listed below).
What To Do:
The pigeon park is my all-time favorite spot in all of San Juan. I don't know if it's because of the novelty of hand feeding birds or if it's because I've been every time I'm on the island, but either way it's always a fun time. Just outside of the entrance to the park, purchase a bag of bird feed for $2 and get your camera ready for the cheapest animal interaction you’ll ever experience. Simply hold out your hand with a little bit of food in it and wait for the birds to flock. If you’re feeling particularly brave, try putting food in both of your hands. You might end up looking something like this:
Or like this:
Or maybe even like this:
You’ll definitely want to have some hand sanitizer on hand for afterwards. This spot also has a great overlook of the harbor, and you can read a little bit about the history of the park.
One of the most obvious landmarks of Old San Juan, El Morro is a must-see for first time visitors. You don’t have to go inside, but that’s where you’ll have access to some of the best views on the island. Inside, you can roam around the fort, gaze at collections of memorabilia, and climb the still-functioning lighthouse. The old fort walls actually line the city, so you can step inside some of the lookout posts all over San Juan and imagine what it must have been like to guard the island from unwanted visitors. While the inside of the fort is a worthwhile stop, the entrance is the most breathtaking aspect of the entire structure. A long gravel path stretching its way to the fort entrance is lined on either side with large grassy areas where people gather to picnic and fly kites.
La Perla Overlook
Adjacent to the right-hand side of the fort lies La Perla, the town where the music video for Despacito was filmed. DO NOT go into the town. Just enjoy the view of the ocean from the hill overlooking it. If you turn around and face the city, you can see where the old meets the new - literally. To the left, the buildings become more and more modern while the buildings to the left represent the traditional colonial style homes. There's a road that follows along this path and loops around the fort, but walking it gives you the time to stop and enjoy the view and maybe snap a few pictures.
P.S. the bar where the dancing scene was filmed is also located in Old San Juan and it's called La Factoría. It's one of the coolest bars I've ever been into, but that's a story for another time.
What To Eat:
For a tad of history and a whole lot of flavor, have a meal at San Juan’s oldest standing restaurant. Appreciate the colonial Spanish interior while sipping on a mimosa or a café con leche. The La Mallorquina brunch special is a steal with a house-special omelette, toast, and a mimosas for just $17. This spot is also the perfect location to get you into the heart of the city, helping you take in the sights of the city before your real day begins.
You may have heard of the island of Mallorca near Spain, but have you heard of the Mallorca bread? If not, you NEED to get yourself down to La Bombonera before the day’s end to enjoy the best treat Puerto Rico has to offer. One of the most famous bakeries on the island, La Bombonera gets their Mallorcas just right every time. They slice the loaf in half, lightly panini it, spread melted butter across the top and add a sprinkle of powdered sugar. It’s so good I’m willing to bet you’ll struggle to just order one. I always get a minimum of 2, and when I can, I get a baker's dozen shipped to my house (I know, I know, it's a super extra thing for me to do, but if you try them, you'll understand).
Often, along the sidewalks and on the outskirts of busy plazas, you’ll find shaved ice stands with the word “Piraguas” written across the side. This Puerto Rican snow cone is a refreshing snack in the heat of the Caribbean sun. I like the coconut flavor the most, but there’s a plethora to choose from, so you’re bound to find something you like. Can't decide which one you want? Get all of them.
There's so much more to see and do on the island that what I've listed here, but these are my top choices for what to do on any given day. Old San Juan is a relatively small town, so you can most definitely do all of these in one day. If you have more time, or if you're more of an outdoorsy person, I recommend looking into El Yunque, Puerto Rico's rainforest, or day-tripping to Vieques or Culebra. I highly recommend Lonely Planet as a resource for more information and ideas for what to do. Whatever you choose to do with your time on the island, I hope you enjoy it as much I do.