Lessons from Puerto Rico: Tips on Taking a Trip and Remaining Friends Afterwards

By Kaye Olsson, I Start Wondering Columnist and Dorian Martin, I Start Wondering Founder

After a long hiatus due to the pandemic, travel is finally back! Airlines and rental car agencies are scrambling to keep up with the demand as seemingly everyone takes to the road or skies this summer. But before you dash off on that next adventure, we offer a few topics to consider to mindfully make your trip more enjoyable, such as how to travel with a companion.


Our input on this is fresh: We recently had the pleasure of spending a week together exploring the island of Puerto Rico. It was a gorgeous place filled with friendly people, delicious food, and lots of interesting history. We had an absolutely delightful time and, upon our return to the mainland, began reflecting on what made it such a positive experience.


Here is a quick conversation we had that contains a few tips for planning a successful trip with a travel partner.


What from your perspective made this trip so enjoyable?


A Puerto Rican sunset
A Puerto Rican sunset

Kaye: One of the aspects of this trip that I liked the most was the feeling of being in a completely different country without the hassles of international travel. Puerto Rico has its own unique culture with different architecture, landscapes, and foods than we see at home. Yet most people we encountered spoke English, the currency was U.S. dollars, and it was easy to drive a rental car across the island. It was the best of both worlds!



Dorian: I agree to everything you said, Kaye. For me, what made this trip so enjoyable was how it seemed to flow once we got started. There was a nice pace to our days with a mix of activities and quiet moments. There also wasn’t a tug-of-war or any drama between us. We managed to deal with the challenges that came up—a four-hour delayed flight, cell phone issues, a cooking class that (pun intended) didn’t pan out—and take them in stride without losing our vacation vibe.


What types of planning made a difference? And what didn't?

Kaye: Certain activities, such as the El Yunque rainforest and the bioluminescent bay tour, had limited capacity and required advance reservations. So planning ahead for these outings was essential. But there was also plenty of wiggle room for spontaneous discoveries along the way, which allowed us to experience amazing restaurants and a rum tour conducted in a “castle.” Having a basic framework for each day helped us prioritize what we wanted to accomplish without being too trapped in a rigid schedule.


Dorian: The other part that was so helpful is that we knew each other well enough that we can identify what we had in common and plan around that. And if there was a question, we would ask each other – and give honest feedback. For example, you knew that I am not a fan of kayaking – although you are – so when there was a kayaking option for the bioluminescent bay tour, you took my preference into account. And we are both foodies, so the idea of taking a guided walking tour of Old San Juan restaurants was an easy selection.


Traveling with a companion can be wonderful --or miserable. What worked on this trip? And feel free to share what we could have improved on?

Kaye: I feel like the most beneficial thing we did was to talk about our expectations ahead of time. We both shared ideas about what we wanted to do while in Puerto Rico, what accommodations we preferred, and who would cover various expenses. This prevented any nasty surprises along the way. Renting a condo with separate bedrooms, instead of sharing a hotel room for a week, allowed us to enjoy each other’s company, then have our own space each evening. It provided a perfect balance of togetherness and quiet time.


Dorian: I think we did a great job of allowing each other space when we needed it on this trip. I can be an introvert, so there was plenty of time in the morning for me to meditate, read and move quietly into the day. And I never felt like there was a secret checklist of expectations on this trip. Also, when something came up – in my case, an achy knee – you were willing to forego our plan to go explore caverns and we had an impromptu beach day instead without any stair climbing or lots of walking.


What was your favorite part of the trip?


A Puerto Rican tropical plant
A Puerto Rican tropical plant

Kaye: That’s a difficult question because there were so many incredible experiences during this trip. But I guess I’d have to say my favorite part overall was how it stimulated my senses. My eyes feasted on the gorgeous colors of the tropical flowers and the turquoise water of the ocean. The wide variety of delicious smells and flavors at the various food kiosks was a treat for my palate. My skin delighted in the feeling of the warm water as I soaked in an outdoor tub. And my ears were filled with the sounds of wildlife and the cheerful rhythms of Latin music.


Dorian: This truly was a perfect trip – and all of our experiences were amazing. However, for me, the best part was getting the chance to spend quality time with a dear friend that I don’t get to see all that often anymore. I think the pandemic has highlighted the importance of relationships for me and I don’t want to take those for granted, especially with people who don’t live in my immediate area.


What was the most surprising part of the trip?


One of the many pristine beaches in Puerto Rico
One of the many pristine beaches in Puerto Rico

Kaye: The biggest surprise for me was the contrast between the northern and southern parts of the island. I had purposely avoided researching too much about Puerto Rico because I wanted each day to be a new discovery. So the drastically different landscape in San Juan compared to Ponce was completely unexpected. The area near San Juan was lush, green, and tropical. But, once we crossed over the mountains to the southern part of the island, it became much more arid with a lot less vegetation. Both were beautiful, just in different ways.



Caption: View from El Yunque National Forest
View from El Yunque National Forest

Dorian: I originally was hesitant about going to Puerto Rico because all I thought it was about was the beaches. I don’t have a special affinity for beaches or oceans, but they were truly beautiful and far more pristine that I was expecting, whether we were in a tourist area or a beach primarily used by families. With that said, I was wowed by the wide variety of terrains, long-standing culture, and true kindness of the people with whom we interacted.


What kind of shout-out do you want to give to Puerto Rico?

Food Options at the Luquillo Kiosks
Food Options at the Luquillo Kiosks

Kaye: All the people we encountered there were warm and friendly. They were also fiercely proud of their island paradise, and rightly so. The place is drop-dead gorgeous with delicious food and incredible history. Despite the difficulty of scarce resources, much of the basic infrastructure damaged during Hurricane Maria (which blew in five years ago) has been repaired, which is a testament to the strength and resilience of the residents.


Dorian: Amen! I also want to thank Puerto Rico for not losing its soul in the chase for tourists. I felt like the island and its people were meeting us without artifice. We didn’t see anything truly out of character for Puerto Rico, other than a lot of fast-food restaurants and business chains. I didn’t feel like the island was trying to be the next Disneyland or Las Vegas. Instead, the citizens valued their culture and the inherent beauty of the island.


Anything else that you want to share?

Kaye: I encourage everyone to take advantage of opportunities to travel whenever they present themselves. It’s a great way to learn about the world and broaden our perspectives. Seeing how other people live always makes me appreciate the little things at home I often take for granted.


Dorian: I had forgotten how lovely it is to travel to new places and to find out how much we have in common with the people who live there. And I want to bring parts of Puerto Rico back with me. This non-beach girl now has a video of the Puerto Rico beach as my phone’s screensaver and has an inside track on Puerto Rican sofrito so I can try to make the amazing beans we enjoyed so often.