How I spent 6 magical days in San Juan Puerto Rico

I love unexpected trips. Normally, I setup my trips at the beginning of the year so I know when to take off work and how much I need to save. My trips for 2019 so far have been: Cuba in April, Dubai in May, New York in July, Barcelona in September, and Chicago in October.

The trip to San Juan wasn’t on my list but one of my close friends (who I went to Dubai with) wanted to go somewhere for her birthday (Halloween baby). After looking at several Caribbean places, I suggested San Juan for 2 reasons – we could fly out of Birmingham instead of having to drive to Atlanta and I hadn’t been since the hurricane and wanted to see just how much it had changed. A $350 round trip flight and $900 Airbnb later, we made our way to the beautiful island of Puerto Rico. Here’s how we spent 6 great days:

Day 1: Flight, Check in

Even though we had to connect in Tampa, our flight to San Juan was a breeze. Breaking up the flights made it easier for me to not sleep on the flight (something I’m trying not to do so as to not interrupt my sleep schedule). After grabbing our bags, we took an Uber to the Airbnb and promptly went to bed (FYI: Uber in PR is the BEST — HAND DOWN!! I’m taking 4-6 dollars for a trip anywhere in Old San Juan and Condado…couldn’t believe the prices)

Day 2: Explore Old San Juan

Our Airbnb was in Old San Juan (Calle San Justo street to be exact) so we spent most of the down just exploring the city – my friend for the first time and me trying to kick up the memories from visiting 5 years ago)


Lunch at Smashed Avocado (Get the Chipotle Chicken…you’re welcome)


Dinner at Lady’s Place. My fish was a little overcooked but the sweet plantains made up for it. Uber was ~ 4 dollars each way from our Airbnb)


Day 3: Gilligan’s Island        

We didn’t want to plan too many excursions because we wanted this to be a relaxing trip but the day trip to Gilligan’s Island was something we couldn’t pass up.


Day 4: Taco’s & Shopping

Day 3 wiped us out but not too much where we couldn’t fit in a day of shopping. After a pit stop at Taco’s + Tequila (Vanderbilt Hotel in Condado neighborhood), we headed to Plaza Las Americas (a big mall but now really worth the hype).

After a day full of shopping, we spent the afternoon/night exploring the night life in Old San Juan and came across a mini concert. The spirit of the people of Puerto Rico was infectious.


Dinner at La Princessa Gastropub


Day 5: Bacardi Tour

I wasn’t able to go on the Bacardi tour that last time I was here, so I made it a point to add it to our itinerary this time. From Old San Juan, you take a $1.00 roundtrip ride to Cantano Island and then a short trip to the Bacardi house (FYI: the bus to take you there is only $3.00 so $6.00 round trip but what they didn’t tell you was that you had to have at least 4 people on the bus. If not, that goes up to $12/person so $24 roundtrip. Save yourself the headache and just order an Uber. $5.13 for 2 people!!)

Day 6: Waffles + Beach Day

We stumbled upon this Waffle place while exploring Old San Juan on Day 2. I don’t know what they put in their waffles but it was DELICIOUS. I try to steer away from pork because of the high concentration of salt but this bacon was AMAZING. I’m not sure what spices they put on this bacon but I was so close for asking for the recipe.


We then took a 10 dollar uber ride to Isla Verde and spend the day at the beach (the Marriott has a day pass you could buy and includes a free drink, access to chairs/umbrellas, and use of their bathrooms and showers to change)



I’ve never spent 6 days in a Caribbean city. I always assumed after Day 4, it would get repetitive but this was anything but that. I could have spent another 6 days in PR and wouldn’t have grown tired of it. From the people to the food to the culture, Puerto Rico will always be one of my favorite islands.


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