Travel Nightmare: The Highs and Lows of Puerto Rico

Another trip, another travel nightmare story! No matter how much I plan and organize before I travel, some things just do not go as planned. This past weekend, my fiancé and I visited Puerto Rico. We are getting married in Puerto Rico next March so we planned this visit to get some onsite planning out of the way.

I want to prelude this story by saying this: We loved Puerto Rico and will definitely be going back (for our wedding and afterward). Unfortunately, we did not have the best experience on our first day of our two-day trip. This was our plan for the first day: land in San Juan, pick up our rental car, drive from San Juan to Rincon (a 90 mile drive), tour our wedding venue in Rincon, meet the caterer for the tasting in Rincon, drive back to San Juan, check into the Airbnb, go to dinner, and finally return the rental car.  

Arriving in Puerto Rico

As soon as we arrived in Puerto Rico, I started sneezing and my eyes started watering unbearably (I am allergic to most flowers/pollen). I decided to ignore my allergies because we needed to quickly pick up our rental car and get on the road. I figured we would pick up some Benadryl on the way.

Rental Car

When we arrived at the rental car office, we were told that our rental car for the day would cost double what we were originally quoted! There were a ton of random fees listed on the receipt but I much as I wanted to argue, I was in a rush and just hopped into the car and got on the road.

Road Trip to Rincon

The drive to Rincon is 90 miles from San Juan. Usually, the drive should take 1.5 to 2 hours. Unfortunately, because of rush hour traffic, the GPS was estimating the trip would take us three whole hours! As soon as we got on the road, we realized driving in Puerto Rico was very different from driving in Florida. There are no dividing lines on the highway, lanes merge without any warning, and most importantly, the road signs are in Spanish (which neither of us speaks). Once out of San Juan, we drove into the more mountainous, hilly regions of Puerto Rico. The roads were narrower, rougher, and twistier making the drive very dangerous and slow. Finally, we made it to Rincon!

We Arrive in Rincon!

When we finally arrived at the wedding venue, we were an hour and a half late. We met with the venue’s tour guide and quickly made our way to the rooftop ceremony/reception area. As soon as we stepped foot on the roof, the skies above opened up! It had been cloudy all day but there was no sign of rain until that moment. We waited half an hour but the rain was not letting up and the tour guide’s shift was ending. So we took a few pictures and left. We got to see our venue space for exactly three minutes.

From the venue, we went to meet with the caterer who was luckily only five minutes away from the venue. This was actually the best part of the day. The caterer served us lunch and delicious rum punch on a beautiful garden patio. This was the most relaxing part of a hectic day.  

Back to San Juan

After meeting with the caterer, we headed back to San Juan. At this point, my allergies were actually killing me. I was struggling to breathe and my eyes were nearly swollen shut. We stopped at a Walgreens and scooped up some allergy meds which cost $8 for five whole pills! Then we got back on the road. The drive back was actually much easier and smoother.

We Arrive in San Juan!

When we arrive in Rincon, we headed straight to the Airbnb. As soon as we pulled up, we knew that we would not be staying there! The listing showed a  modern one bedroom condo with a gorgeous waterfront view. What the listing did not show was the outside of the building. The building looked like it was abandoned and ready for demolition - several windows were shattered and/or boarded up. They say you should not judge a book by its cover but you can definitely judge an Airbnb by its cover. I immediately called my parents panicking (I am not a real adult, don’t judge me). They found a nearby hotel that they had stayed at before and booked us a room (thanks, Mom)! We canceled our Airbnb and headed to the rental car office.

After returning the rental car, we called an Uber to take us to the hotel. When the Uber driver pulled up, he hurriedly ashed a blunt (yes, you read that right)! He hopped out of the car looking very paranoid and helped us put our bags in the trunk. Although the drive to the hotel was less than ten minutes, I seriously thought I was going to die! The driver was texting while driving, swerving in and out of lanes, and he even hit a curb.

Finally, we arrived at the hotel, somehow still in one piece. We checked in, got settled, and knocked out for the night!

Despite having possibly the craziest, most unorganized day, we truly enjoyed the remainder of our time in Puerto Rico and will be returning very soon. We stayed at the Sheraton Puerto Rico Hotel and Casino which is an amazing hotel!


What travel nightmares have you experienced? How did you change your trip for the better afterward?


Felicia aka Ms. Shopaholic Diaries