24 Hours in Old San Juan
If you google “Puerto Rico” your computer screen will probably light up with the blue, pink, and yellow buildings which have come to be synonymous with Old San Juan. FUN FACT: Old San Juan wasn’t the original capital of Puerto Rico. The original location was further inland, but was shortly deemed insufficient for military and trade reasons. The people of Puerto Rico decided to relocate to a peninsula now known as Old San Juan. Characterized by pastel colored homes, cobblestone streets, rolling hills, and historic military forts, Old San Juan is a barrio not to be missed.
Because George (le boyfriend) and I had limited time in Puerto Rico, we were concerned about scheduling all of our excursions in lieu of leaving extra time to roam the sights and streets of Old San Juan. However, we were able to hit all of our spots with a 24 hour window of time!
So, L&L’s “24 Hour Guide to Old San Juan” will hit all the hot spots you won’t want to miss!
Don Ruiz Cafe. We started our day in Old San Juan at the tip of the old city. Don Ruiz Cafe is located within an old barracks building across from El Morro. We stopped for some coffee and a quick breakfast sandwich before our full day of walking. Their list of specialty lattes was extensive (and delicious!), and both George and I were impressed with our breakfast choice.
El Morro. An old, historical castle/fort with a rolling lawn (many locals fly kites, picnic, and run drills in this space) and a long walk up to the entrance. This was my favorite part of the day. The VIEWS are incredible! You can watch the blue waves crashing on the black rocks and then turn around for a view of the city. Fantastic. I wouldn’t have minded watch duty as a solider, at all. Our taxi driver told us the legend of El Diablo. Legend has it, El Diablo would cause the waves to crash up on the side of the fort, sweeping away the soldiers at watch (when, really, they probably just snuck away to meet with their girlfriends). Interesting to imagine while looking out to sea!
Self-guided walking tour of Old San Juan. We used this guide, and I wore these shoes (lots of hill climbing and cobblestones). We enjoyed exploring at our own pace while learning more about the different historical buildings while working our way to the busier side of town. Be sure to stop and enjoy the views!
Eddie’s “Stickless” Popsicles. Eddie’s is very incognito, but we managed to find ourselves this hidden gem! The day had warmed up, so we were in need of a frosty treat. And, I think I paid less that $1 for my popsicle! (Rumor has it - his little shop has served royalty before).
Cathedral of Old San Juan Bautista. We stumbled upon this cathedral - it sits on the front edge of a cute little plaza! The architecture is noteworthy and there is usually some sort of street musician playing in the plaza.
Paseo de los sombrillas. Probably one of the most photographed streets in Old San Juan! Just follow the throngs of tourists, and you’ll find it. The rainbow of colors found hanging above your head reflect the colors found throughout Old San Juan. It was originally created as an art project to attract visitors (and display San Juan’s colorful resilience after Hurricane Maria). Wake up early if you want to capture a good picture! Or. Get caught in a short rain shower whilst standing beneath the umbrellas. The Governor’s Mansion (a pretty powder blue) also makes a pretty backdrop for your photo.
Barrachina. The birth place of the pina colada! We stopped in to this restaurant for a much needed respite. The indoor patio is colorful and feels slightly secluded from all the hustle and bustle. The food is also delicious, so don’t just order a pina colada!
The Puerto Rico Flag Wall. This wall is located on Calle San Jose just around the corner from La Factoria! The colorful flag mural was originally painted to showcase local island pride. It was recently repainted in black and white as a political statement to raise awareness about the hardships the island is currently experiencing. Don’t miss this spot.
Calle San Sabastian. Looking for nightlife? This is where you’ll find it. You’ll find bar after bar after bar on Calle San Sabastian, all with the windows and doors thrown open as to invite their visitors inside. Tabero Lupelo was a fun spot!
La Factoria. This bar is about as nondescript as they come, but something I would deem a MUST. The “Despacito” music video was filmed in this bar, catapulting it into the global spotlight (and for good reason - their cocktails are FAN. TAS. TIC.)!
We also managed to pop in and out of a few shops, galleries and rum tasting bars! In total, we walked over 8 miles on this day, so be prepared to get your steps in!
We loved exploring Old San Juan. There is so much history to see and pastel colored buildings to admire.
