(Scroll down to see Part 2 – where everything turns around for me)

The best way to explore Puerto Rico is to just rent a car in San Juan and drive from one side of the island to the other.

From surfing in Rincon to the beaches in Vieques, Puerto Rico is so much more than what lies within the capital city walls. Not making a day trip to El Toro Negro Rainforest or El Rio Camuy Caves at the very least would be a big disappointment.

Thanks to an invitation by the San Juan Marriott, I had the opportunity to explore Puerto Rico for myself and uncover some amazing gems along the way.

I can honestly say that the raw beauty of Puerto Rico blew me away. It crushed my expectations.

After spending a week at the San Juan Marriott and exploring Old San Juan, I decided to rent a car and set out on a four-day road trip around the country. Here’s a recap of how the adventure played out…


Renting a Car in Puerto Rico
Arriving in Rincon, Puerto Rico at Sunset

Most rental car companies in San Juan have office locations at both the International Airport and tourist areas of Condado or Isle Verde, so the first thing you need to do is find the best pick-up location. I was flying to Miami Beach after I returned the car so I shopped around the best daily rates and took the bus to the airport from Old San Juan to rent the car.

I got a rental from Thrifty for $10/day.  Like anytime you’re renting a car, you have to be aware of meaningless fees and other bologna they try to throw at you.

After an awesome BBQ next to the rental place, I made the two-hour drive from San Juan to Rincon just in time for sunset.

I didn’t have a smart phone or GPS, but the Thrifty office gave me a couple of tourist maps that actually did the trick. There are a few major highways that run across Puerto Rico so it wasn’t too hard to navigate.

Rincon is a small surf town on the west side of the island that features picturesque sunsets with surfers dotted across the horizon.

I watched the sun set until the last surfers came to shore and then I had dinner and a few rum punches with locals at the Calypso Bar & Grill at Maria’s Beach.

I slept in my rental car at the beach the first night because, well, why not?


Surf Lessons in Rincon, Puerto Rico
Surf Lessons in Rincon, Puerto Rico (the only proof I have after the accident)

Bitter sweet. My first surf lessons ever left my drained and disappointed. Despite catching a few nice size waves and loving every minute of being out on the water, the entire experience was overshadowed on the first wave when I lost my brand new GOPRO HERO 3 Camera.

My head strap flew off as I tried to catch my balance on a wave over my head and it was sucked under and swept up by the coral reef below.

I tried renting a snorkel and swimming back out to where I might have lost it, but, no luck.

I tried filling the whole in my heart with a big, traditional lunch and then decided it was time to move on to Ponce.

Ponce is the second most populated city outside of San Juan and sits on the Southern Coast of Puerto Rico.

Not booking any hotels in advance sometimes comes back to bite me, and finding a hotel/hostel in Ponce was one of those times.

I had to settle for a $80/night hotel called Hotel Belgica in the center of Historic Ponce. It was a little more than I would have liked to pay, but the location was perfect.


This is what travel is all about!

I drove from Ponce to Fajardo and checked into the Moon Light Bay Hostel where I immediately ran into a fun couple who knew the area really well.

My goal was to take a Kayak tour around one of the famous Bioluminescent Bays, but before I could decide on which tour operator to choose, the couple convinced me to drop my tentative plans and catch a ferry to the island of Vieques for the night.

Without much hesitation I agreed and the next thing I knew we were sipping cocktails as the sun set on Vieques.

And then there was the Bio Bay. An experience that deserve it’s own post. Stay tuned for the story of my most amazing travel experience to date. Seriously.


Sun Bay Vieques Island Puerto Rico
Sun Bay, Vieques Island, Puerto Rico, Yes, Please.

I woke up in President Obama’s head writers house. True story. She rents it out while she’s not in town and luckily; a friend of a new friend had an extra couch for us to crash on.

I spent the entire day with the new crew as they showed me around Sun Bay and all the beautiful beaches.

Watch Part 2 of the Puerto Rico Road Trip to get a real grasp of how incredible the beaches were.

I finally had to catch the last ferry back to Fajardo and drive to San Juan to return my rental car and catch the flight to Miami. 

What a trip.


My name is Gareth Leonard, a Marketing Director turned World Traveler with a passion for slow, meaningful travel. I have been traveling the world full-time for the past 9+ years and document it all on Instagram and YouTube. Come join me!


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