Scavenger Hunt: Things to Find in Old San Juan (Puerto Rico)

When I picture a classic Caribbean town, images of brightly-colored row houses with strikingly white columns and charming balconies come to mind.  Old San Juan meets all your expectations.  There are beautiful cobblestone streets straight out of the 17th century.  They twist around the buildings and up hills, creating small parks around every corner.  And the sound of the ocean waves is never too far away.  You’ll feel like you’ve stepped into a pirate movie.

The only way to explore Old San Juan is on foot.  There are plenty of segway tours you can find, but I just feel like that keeps you from taking in the peacefulness of the experience.  Puerto Rico is on island time; everyone is pretty relaxed and slow-paced–unless you’re driving!  If you’ve been there, you’ll know what I mean.  If you haven’t, I’ll let you find out for yourself.


Before you head out on your Must-See list, take a minute to just explore and see what you find.  There’s nothing I love more than slipping into island time and leaving your worries behind.

I love all the cute little details in Old San Juan–the skinny black lamp posts, the trees lining the streets like umbrellas, and benches and parks literally everywhere you turn.

So here’s our scavenger hunt to help you explore Old San Juan:

#1 Find your favorite colorful row house.


#2 Find your favorite little park or sitting area.


One of my favorites is Plaza Darsenas.  Find it here:

#3 Snap a picture of the views from the top of Castillo San Felipe del Morro.



There were so many people calling this a castle when I was there because of the name “Castillo,” but El Morro is actually a fort built in 1539.  This is where the Spanish defended the island against invaders.  It has such an interesting history that you can read about here.

#4 Find a doorway that’s almost your same height.


People must have been shorter back the 1500’s.  All the little rooms of El Morro paint a picture of Caribbean life in the 16th century.

#5 Take a picture of the coolest kite you see on the huge lawn outside El Morro.


It’s always breeze up here, and you kind of feel like you’re on top of the world.

Find El Morro here:

Complete your scavenger hunt at Senor Frogs.


And don’t forget to take a picture on their hilarious barstools.  When I posted this picture on Facebook right after my trip, my great-aunt saw it and actually thought that was my butt!  My little cousin was looking at the computer with her, and she covered it up to keep him from seeing.  SMH.

Find Senor Frogs here:


Have fun exploring Old San Juan and finding your own hidden gems to add to the scavenger hunt.


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