I missed Old San Juan, Puerto Rico the moment I left it, and you will too when you visit this beautiful island in the Caribbean. My best friends and I had been planning for a tropical trip outside of Miami for a while. Although we get summer all year round, we wanted the actual tropics. These 72 hours in Old San Juan, Puerto Rico will give you all the adventures you need.


I know a lot of the times, resorts are the go to when visiting the Caribbean, but I dare you to do something different. Stay at an Airbnb with your gals like I did with mine. We wanted to be in the heart of Old San Juan, and we did just that. You have to try it when you visit. You’ll feel like a local and not a tourist. We stayed at the following Airbnb . We didn’t have room service to make us breakfast or pick-up our beds, instead we had our messy-selves and our phone alarms to wake us up for days filled with road trips, long food stops, and A LOT of pictures from one side of the island to the next.


There’s way too much to do in Puerto Rico as a whole that I will highly recommend a 5-6 day trip to explore it entirely. However, if you only have a weekend (Friday-Monday) you’ll be able to use this guide to help you get around.


In Old San Juan, take your time walking the streets and getting the feel of being there. Explore the streets while walking to the best breakfast ever – Calicultura. It is thee most Instagram worthy café ever. After, drive an hour away from Old San Juan into El Yunque and enjoy a day filled with hikes and waterfalls.


Nothing like waffles for breakfast, am I right or am I right? Head over to Old San Juan’s famous Waffle-era Tea Room.

The waffle options are infinite and the service was superb. Filling enough for all the hike you have left to do on this day. On a two-hour drive you’ll head over to Cueva Ventana – possibly one of thee most beautiful sights you’ll ever see. Along with Gozalandia – a gorgeous waterfall with a swing.  If the time permits, drive to Crashboat Beach and soak in a colorful sunset in the Caribbean.


On your last day, I suggest staying in Old San Juan and walk around to El Morro. This area is very touristy and not my cup of tea, but the view is phenomenal and it’s a must if you visit Puerto Rico. I would recommend you drive to the nearest beach to hang out for the day after exploring. Swing by Senor Paleta for icicle pops or Bad Ass Coffee in case you’re in dire need of any.


The nightlife in Old San Juan is better than I ever expected. You can visit La Placita (tell your uber driver about it, he knows!!) or San Sebastian St. where you have bars for days and clubs to dance in for hours – one of my favorite bars was La Factoria. It’s supposed to be amongst the best 50 bars in the world according to TripAdviser.

If you’re looking for places to eat at night, try any of these restaurants:

St. Germain Bistro & Café (has a rooftop!)

Verde Mesa

Triana Tapas & Flamenco

Rosa de Triana

Barrachina – the actual place that invented the Piña Colada


  1. RENT A CAR – Book a rental for your day road trips, because there’s no other way to get around if you’re planning to explore the island. I book all my car rentals through priceline. The parking in Old San Juan is not as bad as expected, there are a lot of parking garages that will keep the car overnight for a fee.
  2. PACK A BOOKBAG – Always pack hiking shoes and a second pair of comfy clothing for change since you won’t be going back to the hotel until later on at night after all your adventures.
  3. If you must, book a different Airbnb closer to the other end of the island for DAY 2 so that you can avoid the 2-hour drive back to Old San Juan, because it can feel like forever. You can always drive back to Old San Juan to catch your flight as well. One thing I learned about this trip is that I can never just stay in one area. To see Puerto Rico altogether, I have to drive the entire coast by car and stay at different airbnb’s per night to see it all. Give it a try!


I took this trip on September 1, 2017 with my friends and we left on the 4th. Hurricane Irma hit Puerto Rico at category 5 two days after we left and Maria a week later at a Category 5 as well. These hurricanes left the island without power and water for months. I have no doubts that the island will be restored to how I left it, because the people of Puerto Rico have that kind of spirit – they’re fighters. They were phenomenal and welcomed us with nothing but kindness.

I ask you to please make any donations to the link below to help restore this island to what it was and to help the community regain their forces.

Hurricane Relief For Puerto Rico

As always, thanks for reading. If you’re interested in travel guides, visit my Havasu Travel Guide.