An interview with A Cruising Couple: high school sweethearts turned world-class travelers


A Cruising CoupleWSGT’s next Travel Influencers are Dan and Casey of A Cruising Couple, here to give you the best of adventure travel with a dash of class!

1.)Where was the first place you traveled that made you think WOW—travel is amazing (think history book come to life or …..)

The first place I traveled that took my breath away, and would later change the course of my life, was Prague. I was only 16 years-old, knew absolutely nothing about Prague, and went all alone. I was mesmerized! I remember walking around the Old Town, seeing the stunning architecture and reveling in the new culture around me. I loved meeting different people from around the world, and loved the challenge of navigating a new language. This is the country that made me fall in love with travel. For Dan, it was his study abroad trip to Australia that really got him hooked with the travel bug. 

2.)If you had unlimited resources, where would you go and what would you do?

That’s a tough question. We’ve left out hearts in so many different countries that we’re itching to go back to, and yet still crave to see the ones we’ve never stepped foot on before. I’d say our first stop would be Antartica. That’s at the top of our bucket list right now and we’re dying to see the landscape so few have witnessed in person. 

3.)What were you afraid to do and how did you find the courage to overcome it?

One of the most terrifying things we’ve ever set out to do was cycle the length of Vietnam. I had never tried something so daring before but I just kept thinking about how rewarding it would be at the end. Reminding myself that there might never be another time to take this opportunity again helped me overcome my fears. I wouldn’t say I started the trip feeling particularly courageous, but I pushed myself to do it anyway, and for that I will always be grateful.

A Cruising Couple

4.)What apps do you use regularly that make your life easier?

My favorite apps right now are Slack and Basecamp. Both of these apps help us easily communicate with our team, no matter where in the world we are traveling. Slack is great for instant communication and Basecamp keeps our lives organized and sane. I also love using Evernote to organize and flesh out blog posts..

5.)What place do you wish more people have seen?

We wish more people have experienced India. There is truly nothing quite like it. From the rich culture, and the incredible historical wonders to the heart-melting hospitality, and insane traffic, India is one place that everyone should travel to, at least once. Whether you love it or hate it, it’s worth the adventure to experience one of the most ancient cultures for yourself. 

A Cruising Couple

6.)Best advice you have been given and by whom?

I can’t remember where I heard this first, but it’s always stuck with me: “Whatever it is that you want to do, just go do it now. There will never be that “perfect time” to travel or try something new. Face your fears. If you feel called to it, then just take the leap.”

7.)When were you surprised by the kindness of strangers on a trip?

Remember how I said cycling Vietnam was the one thing that terrified me most? Well, of course, during one of our long cycle routes, through the middle of who-knows-where, an insane thunderstorm rolls out of literally nowhere and we were forced to pull over and take shelter under a tree. Google maps and cell service had totally failed us, and we were lost, far from any hope of a hotel to stay the night at. As the storm intensified and we began to fear for the worse, a small-framed Vietnamese man motioned to us to come into his home. He let us stay the night, in their one-room village hut, giving us the only bed, while they slept on the floor. They welcomed us in like family, and did all they could to make us feel right at home. Although we couldn’t speak their language, and we were total strangers, they extended more hospitality and love than we had ever experience from people we didn’t know. 

A Cruising Couple

8.)What inspired you to travel for extended periods of time or live in a new country?

Ever since my first international trip, I fell in love with travel and never quite looked back. I studied International Relations and always knew that travel would forever have a place in my life. I sort of fell into the expat life without having made much plans or expectations. Dan and I first set out to Taiwan to teach English as newlyweds, and somehow we never really ended up returning long-term to the US.

9.)I travel because….

I travel to experience as much beauty, kindness and adventure as possible. I travel because it reminds me that we all have the same basic needs, and makes me feel connected to humanity on a deeper level. I travel because having global connections and relationships makes the world that much smaller, and with so much fear and hate, we could all use a little more love and unity.

A Cruising Couple

For up-and-coming travel writers, Casey recommends: Lonely Plant’s Guide To Travel Writing is a great place to start. This books helped me tons when I was just starting out.

We met when we were a young 15 years old. We began dating at 17, the start of our senior year in high school. We tied the knot at the ripe old age of 22 – a week after graduating university. We’re high school sweethearts and now a married couple in our late 20s. The years between meeting and marrying, we had our ups and downs just like anyone. We were both bitten with the travel bug from an early age, and though we were madly in love with each other, we were also taken with the world. We spent months and semesters separated by continents, exploring other countries on our own. But no matter how far our journeys took us, we always returned to each other.

It should come as no surprise then that we dreamed of a life of travel together. We decided that after our wedding we would move across the globe to teach and travel in Taiwan. However, before we left, we wanted an epic, adventurous, one-of-a-kind honeymoon. A trip we could never replicate in the future. A trip that would prove our marriage could handle anything.

We decided on a 7-week honeymoon road trip traversing the United States. We started in North Carolina, headed over to California, went up to Seattle and then crossed back to our home Tar Heel state once more. We spent every waking moment together adventuring around the US—and we loved it!

Rather than having a wedding registry for home goods we wouldn’t use, we set up an online registry for contributions towards our road trip. We were gifted with amazing experiences, like hot air ballooning in New Mexico and wine tasting in Napa Valley. We were so blown away by the support and generosity we received from family and friends that we decided we needed a way to keep them involved on our honeymoon that they had made possible.

Hence, the birth of our travel blog: A Cruising Couple. We would “cruise” our way around the US in a ’97 Volvo Station Wagon. We would dub ‘Cruising Together’ our theme song. We would blog about the entire trip. And that would be that.

A Cruising Couple

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Caitlyn O'Brien

Caitlyn is a 26-year-old Canadian with a passion for travel, futbol, and more recently kayaking in her new Patagonian home: Futaleufú. She teaches English at a local school and loves turning her daily experiences into stories.

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