8 Hours In Old San Juan, Puerto Rico

(Last Updated On: April 24, 2020)

8 Hours In Old San Juan

8 Hours In Old San Juan, Puerto Rico

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Before I jump into telling you all what don’t want to miss in Old San Juan, Puerto Rico, I thought I would share a little about me incase you haven’t stopped by my blog before. Hi! I’m Jane and I started Plain Jane Lifestyle as a fun creative outlet to write about travel, food, coffee and blogging!

If you are thinking about starting a travel blog, or any type of blog for that matter, here are a few of my most popular past posts that will help you get started: What Every Blogger Needs To Know About Blogging Legally and Start A Blog In Less Than 10 Minutes With Siteground (affiliate).

 Okay, now back to Old San Juan, Puerto Rico…

I recently returned from a week long cruise in the eastern carribean and Puerto Rico was one of my favorite stops! My husband and I only had about 8 hours to spend in Old San Juan before we had to reboard our cruise ship.

I am going to give you the perfect 8 hour itinerary of things you cannot miss while in Old San Juan, Puerto Rico. And, I promise you can get this all in in just one day!


Make your first stop be the tourist information center at Casa Alcaldia / City Hall – located at the top of San Francisco Street at Plaza de Armas.  153 Calle San Francisco, San Juan, 00901, Puerto Rico.  Here you can talk to the experts who are happy to point out points of interests of the local sights as well as provide you with a free map of Old San Juan.


Now that you’ve got your tourist map, it’s time to get caffeinated and get some breakfast in your belly before a big day of sightseeing. Stop at Café Cuatro Sombras in Old San Juan for a micro-coffee experience. The coffee beans are grown in the shade right in Puerto Rico, you can’t get much more local than this.

I got the iced Americano with a little milk, I highly recommend this local shop. This local café is so proud to serve locally sourced coffee beans grown on the island that for only $12.00 you can get a tasting tour, for $75 you can taste and learn how to properly brew coffee using a French press, chemex, pour over and syphon.  You can participate in a coffee cupping workshop taught by a local coffee testing specialist and learn the professional way to taste and evaluate coffees.

If you are a coffee enthusiast like me, this is an experience you don’t want to miss. Learn more here.

Cafe Cuatro Sombras in Old San Juan
Cafe Cuatro Sombras in Old San Juan

 10:30am- Walk by foot to Castillo de San Cristobal, the largest Spanish fort built in the world! For only $7 you can get an admission ticket to stroll the entire fort at your leisure. FYI – This ticket is good to also use at the El Morro fort if you go within 24 hours of ticket purchase. So basically you can get two forts for the price of one!

Oldest spanish fort in the world, Old San Juan, Puerto Rico

This is also the perfect spot to get some great views of the city!

And for some fun Selfie pics!

We spent about an hour and a half touring the fort, it was well worth the $7 admission fee!

Castillo San Felipe del Morro   Castillo San Felipe del Morro   Castillo San Felipe del Morro   Oldest spanish fort in the world, Old San Juan, Puerto Rico


Lunch time! We did not necessarily have a plan for lunch the day we were strolling around, and we just happened to walk by the cutest tappas restaurant called T.Tuan Old San Juan, and after looking over the menu outside we knew this place was going to be good.

We learned from our waitress that the restaurant had just opened two months earlier. The location was so picturesque, as it sits atop a hill that looks over the port of Old San Juan.

San Juan, 00901, Puerto Rico

I decided to get a Pina Colliada and Nathan got a cornona! This was the best pina colliada I had on the trip!

Pina Colliada at T.tuan cafe

The food was amazing! I love the tapas family-style concept. It’s a fun way to try lots of different things. Here’s what we ordered:

Steak Crostini at Jtuan cafe in old san juan
Steak Crostini
Mahi mahi sliders
tuffed Peppers at Jtuan Cafe in Old San Juan, Puerto Rico
Stuffed Peppers with cheese
fish tacos at Jtuan cafe
mahi mahi fish tacos

1:30pm –

Next door to T.Tuan restaurant sits the smallest house in the world.

That's me (J. Boughton) standing next to the smallest house in the world!
That’s me (J. Boughton) standing next to the smallest house in the world!

Stop by to for a fun photo op and then you can say you’ve visited the Guinness book of world record’s tiniest house!

The smallest house, or “La Casa Estrecha” which is the Spanish words for “narrow house” is just 5 feet wide and 36 feet long from front door to back wall.


Not too far from the smallest house, sits La Casita Rums.

Stop by La Casita Rums for a rum cocktail like no other. Did you know that Puerto Rico is famous for it’s rum? That’s right. the Bacardi rum factory happens to take place right in Puerto Rico. In fact Puerto Rico is nicknamed the “rum capital of the world.”

downtown old San Juan fountain


Stroll the quaint streets of Calle del Cristo in Old San Juan and do some shopping, (or window shopping). All while taking in the architectural beauty of the colorful downtown streets. You will feel as if you were walking in in Barcelona, Spain.

Street in Old San Juan, Puerto Rico old san juan street sunshine peeking through in old san juan Colorful street in old san juan house in downtown old san juan Pretty house in old san juan colorful downtown old san juan


Walk to Colon Plaza (Columbus Plaza) to check out the statue of Christopher Columbus. The statue sits at the entrance to Old San Juan between Fortaleza Street/Ponce de Leon Avenue and San Francisco street.


Take a walk just one block south of Colon Plaza and grab a bite to eat at Café Puerto Rico.

Cafe downtown old san juan

I hope you enjoyed this 8 hour itinerary of how to spend the perfect day in Puerto Rico!


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