Welcome to Old San Juan, Puerto Rico!
We spent the day exploring Old San Juan, Puerto Rico to find out the best things to do in the old city. We started at one of the furthest points in the town, an old fortification called Castillo San Felipe del Morro. Afterwards, we headed out into the city and come across a beautiful courtyard which is a part of the Museo de las Américas. Later, we went to the Paseo de la Princesa which is a promenade which comes alive on Sundays with vendors and even people dancing salsa. After this, we headed up the street to find the famous umbrellas on Fortaleza Street. Lastly, we decided to try a famous Puerto Rican drink (you might have heard of it!).
Castillo San Felipe del Morro
Today we’re exploring Old San Juan in Puerto Rico. We're starting at the farthest point which happens to be a fort so we're on the main part of the grounds. There is the main fortification behind us and there is a huge ground of people flying kites. This place is called Castillo San Felipe del Morro. As we were walking around, we were very impressed that this place dates back to something like the sixteenth century. It is probably one of the oldest parts of the old city, but the city itself dates back to 1521 and we read that it happens to be the second oldest European city settlement in the Americas second after Santo Domingo, Dominican Republic. We didn’t actually head inside of the fort but it’s worth a visit just for the views alone.
Pro Tip: Be prepared to walk in this city! We found some pretty steep hills. We walked an hour and a half from the new part of San Juan itself to get over here and it is an extremely hot day!
Museo de las Américas
Afterward visiting the fort, we headed out into the city and come across a beautiful courtyard that reminded us quite a bit of Southern Spain. The courtyard is part of the Museo de las Américas but you don’t have to pay to go into the museum to see the courtyard. We just came up to see if we can go in and we discover that we can. This courtyard is gorgeous and reminds us a lot of some of the places we visited in Sevilla, Spain.
Pro tip: This city is so colourful, if you’re looking for some great Instagram spots you’ll find colourful areas and buildings all over the place, in fact, you can find pretty much every colour imaginable.
Senor Paleta
After walking around even more we decided to stop for a cool, icy treat at Senor Paleta. It’s a small but unique ice cream shop. Expect a line up but it goes quickly! They have numerous flavours of Paleta or Ice Cream on sticks (popsicles). This is a must visit in Old San Juan, especially if you’re looking to cool down.
Pro tip: Never, ever travel without your travel insurance! We always travel with SafetyWing (and we highly recommend it), it’s our go-to travel insurance as it’s easy to set up and use. It’s great for long and short term travel as well.
Paseo de la Princesa
Our next stop was an area called Paseo de la Princesa. It is a pedestrian walkaway. Usually, it is pretty quiet during the week. But on Sunday, all the vendors and everything is around. We saw everything from Churros to places to get drinks and there are local crafters. Also, there was a huge dance party with the seniors Salsa.
At the end of the walkway we discovered a pretty impressive fountain. It's kind of deceiving that the water goes down and then it comes back up and you actually get a little wet. However, it's kind of refreshing on a hot day. It does remind us of an epic fount in Rome but there are fewer people here.
Fortaleza Street
No trip to Old San Juan is complete without coming to see the street with the umbrellas. If you go on Instagram you're gonna be able to see it everywhere. We were here on a previous day during the week and there were maybe 10 or 15 other people at the time. Today is Sunday, it is pretty wild down here, we came on purpose today because we wanted to see what it would be like on a busy weekend. There is a couple of cruise ships in the port today so this area is jammed at the moment. If you come from Monday to Wednesday you pretty much have the street to yourself.
Pina Coladas
It's now 4:00 PM and thirty degrees and we're still walking around. We're on the hunt for a very famous drink in Puerto Rico. We are going to the place where the very famous drink was invented called Barrachina. This place always seems to be busy. Apparently, a guy that worked here invented the famous cocktail the Pina Colada. However, he then maybe went to go work at the Carib Hilton, so they also like to take credit for this drink as well. Arguments on the exact bar it is invented in, the Pina Colada is definitely from Puerto Rico, and in some form it was created at this very restaurant. We order our Pina Coladas which arrive at our table. IAt first, we were hesitant because it did come out of a machine and didn’t appear to be handmade. Nevertheless, it tastes really good. There is lots of pineapples and coconut flavour too. They did a good job of making it look nice with cherry and the umbrella on top. There's a perfect texture of that icy goodness and we don't taste the alcohol right away. It was delicious.
Wondering where to stay in San Juan? We based ourselves out of New San Juan (we found it to be a bit more affordable. But both New and Old San Juan have loads of accommodations for all budgets! We almost always use Booking.com to book our accommodations (we’re currently Genius level 3 which gives us some great perks, like free upgrades). Check prices and availability here on this handy map:
Watch our full day in Old San Juan Here:
*This blog post might contain affiliate links, which means when you click and book (at no additional cost to you) you help support this blog.
