Puerto Rico is such a diverse and amazing island that is worth visiting and honestly should be on everyone’s bucket list. I would just like to say before we get into things that I would strongly urge you to explore more of the island than just the city of San Juan. Many of the best things to see are scattered all over the island. This guide to Old San Juan is a great place to start though.
This guide is for things to do in Old San Juan which is the historic part of town and has most of the touristy things to do. Parking is scarce so taking an Uber isn’t a bad idea but if you rented a car like we did then there is a parking lot that costs only $3 per day. Just type “Parking Old San Juan” into google maps and it’ll take you there.
San Juan is a popular port city so the busiest time is when the cruise ships are docked. Usually between 9 AM to 5 or 6 PM. We got in about 8:30 one morning and had the whole place to ourselves other than the people going about their day to day work.
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Umbrella Installment
There is a very fun umbrella installment at one end of Fortelenza street. Right in front of the governors house. Stop here first to avoid the crowds and grab some pictures. The umbrellas are changed out fairly frequently so you never know what you’ll get.
I’ve seen them be all pink, multi colored and while we were there they were a light camo. Right after we left they had a holiday and put up a very large PR flag! Wish we could’ve seen that.
Colorful Colonial Buildings
San Juan was first settled by the Spanish during the time of exploration and discovery of the New World. The colonial style buildings with iron balustrades are painted in fun, vibrant colors very similar to New Orleans.
They are fun to look at and perfect for bright pretty pictures! Spend some time wandering the streets of Old San Juan and enjoying its unique architecture and culture.
We were in Puerto Rico in the fall of 2019, two years after the hurricane and although there is still evidence of the devastation caused by the hurricane they have done a great job recovering. While you are walking around see if you can find the buildings that were abandoned after the hurricane.
Forts
There are two forts in San Juan, Fort San Felipe del Morro and Castillo San Cristobal. They are a twenty minute walk from each other and very easy to reach by a short Uber ride or a stroll through the Old San Juan area.
There is a $7 fee that gets you into both forts. They open at 9 AM and close at 6 PM. We went right after 9 and we have the place almost entirely to ourselves for a good 40 minutes! They have lots of signs up describing the use of each area and you can explore everything as you please. Such a fun place to explore.
Drink Pina Colada’s at Barrachina
Next on the guide to Old San Juan is pina coladas!! Did you know that Puerto Rico is home of the Pina Colada? That’s right that delicious blend of coconut and pineapple creamy goodness was invented right here in Old San Juan at a restaurant called Barrachina.
Whether you take it with alcohol or virgin like myself you HAVE to stop here and grab one for yourself. And really you should be ordering them all over the island because they are incredibly refreshing pretty much everywhere any time of day.
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- Everything You Need for an Epic Vacation in Puerto Rico
- The Ultimate Cruise Packing List
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Beaches
There are SO many beaches to visit in Puerto Rico that are stunning and beautiful. However, if you are looking for one that is close to Old San Juan, we enjoyed Playita del Condado when we stopped there in the afternoon to cool off from the sun.
It is a smaller beach but the waves were small, the sand was very nice and the water was great! You can either post up on a towel for free or pay $20 for two beach chairs and an umbrella.
When we were lounging on the beach there was even a cart selling drinks on the sidewalk next to the beach! Definitely a kid friendly, fun place to stop by.
Shopping
Old San Juan is the perfect place to do any shopping you need to do. They have great souvenir shops if you enjoy the classics like me. I actually collect one keychain from every place I visit.
They also have clothing shops and jewelry shops. Plenty of places to find the perfect gift for the people at home (or yourself) and spend a little money.
Dessert at Senor Palenta
After wandering around and exploring you’re probably getting hot. I know I was! The humidity in Puerto Rico is no joke so it feels hotter than the perfect 80 degrees your phone says it is. This gourmet popsicle shop, Señor Palenta, is the place to go.
They have so many flavors to choose from and you have the option to add toppings. I had the strawberry lemonade. It was yummy and perfectly refreshing.
Verda Mesa
Once you get hungry be sure to try Verde Mesa for lunch or dinner! I know it’s food but I HAD to include it on my guide to Old San Juan because it is that good.
We went for lunch and had the best tasting food! It is not necessarily traditional Puerto Rican food but it is all locally sourced and farm to table so you’re supporting several local businesses by eating here. Plus it has the most whimsical and victorian decor. So unique!
Start off with one of their juices or fusions. I had the orange, pineapple and tarragon fusion that was very flavorful. I also got the soup of the day which was a rich potato stew of some kind. It was probably my favorite meal on the island.
I know you’ll enjoy whatever you order. The staff is very friendly and don’t be afraid to ask for local recommendations. They gave us some beach recommendations that were spot on.
Sailing Tour
My birthday was right in the middle of our trip to Puerto Rico and as a gift my husband surprised me with a sunset sail in San Juan’s bay. It was so fun to see the city from the water, you even get to go past the del Morro Fort. The sunset was beautiful to watch.
The crew consisted of two men who were very nice and great at their jobs. We did a group sail so there were 6 people total which we enjoyed because we got hear about their trip and what they’ve enjoyed so far. I always love talking to other travelers and sharing tips and favorite experiences as well as hearing about where they are from!
We booked from Sail San Juan Bay on Airbnb Experiences. If you are a first time user of Airbnb use this link for $15 off any experience you choose and $40 off your first booking.
Practical Information for Visiting Puerto Rico
Find accommodation, sign up for a local tour or buy your Puerto Rico Travel Guide.
Old San Juan Guide
Well there you have it! That is the colorful city of Old San Juan, the oldest city in the United States and its territories. Like I mentioned at the beginning be sure to see more of the island if you have time. Did you know Puerto Rico is home to the worlds longest zip line? And three of the worlds five bioluminescent bays! With so much to see and do you’ll never be bored.
Although it has been over two years since Hurricane Maria devastated the island in 2017 there are still places you can see where things have not fully recovered. You visiting helps the locals so much in rebuilding their businesses and lives so much. Really it would be irresponsible of you not to visit. 😉
Just kidding but I hope you make it here soon!
