The Travel Questions I Wish More People Asked Me

People often ask me, “What’s your favorite place you’ve ever been?”

It’s a fair question, and a hard one to answer.

I’ve lived in nine countries and traveled through more than eighty. Some places stunned me with beauty. Others surprised me with quiet moments of connection or discomfort that I didn’t expect.

When I think about travel, I find myself wishing we started with different questions. Like:

– Where have you felt most alive in your travels? (For me, India.)

– What kind of places have challenged and changed you? (Volunteering in the Peace Corps in Albania.)

– Where have you had the most unplanned connections with locals? (Definitely Mongolia.) – Where have you felt the most uneasy? (Yemen.)

– Where would you return to in a heartbeat? (Argentina, because you could never see it all.)

I’ve also learned that the most hyped moments aren’t always the most moving ones. We recently saw the northern lights in Finland. They were vivid green on my phone camera, but in person they looked more like a funny-shaped white cloud.

Still, I’m still glad we saw them. It reminded me how much of travel is about what experiences feel like, not just what they look like in pictures afterwards.

My point is, the answers to these questions don’t live in a search engine.
But they shape the kinds of trips that stay with you long after you’ve unpacked your bags.

If you’re thinking about a trip — for this summer or someday — and want it to be more than just a vacation, I’d love to help you explore the questions that matter most. Feel free to reach out.

And if any of these questions resonate with you, I’d love to hear your answers, too.