The Hipster Travel Guide wants to know what makes you get up and go. While you may have no problem talking to strangers in Prague, many more people are quite content to stay where they are. Roughly three quarters of the U.S. population doesn’t have a passport.
When did you first know you needed to spread your wings? And the first time, did you fly a little too close to the sun? What was your first trip? Is there one you didn’t take that you wished you would have?
Perhaps your inspiration will pay it forward and help someone else hop on a plane or explore the other side of the tracks. Thanks.

I can’t say that I really knew my grandmother when she died, I was 11. But I knew she was the light in my grandfather’s eyes, and I loved him very much.
My grandmother, however, kind of scared me.
At the end of every visit, she would chase me down to kiss and squeeze me, her lipstick leaving little marks all over my head. For me, it was a death by a million little pecks and I would hide under the dining room table whenever they brought their suitcases downstairs.
A few months after she died, my grandfather arrived at our door, his blue GMC pickup parked in a New Jersey snow drift. The sparkle missing, his laugh muted, my grandfather’s booming voice seemed deflated and his stare looked unsure. He was heading to Lakeland, Florida, to open the winter home they had purchased a year earlier. Retirement was finally at hand but Madeline wasn’t.
My parents decided I should go with grandpa. I don’t know why, but I didn’t care. I grabbed all $41 I had saved up, packed a bag and jumped into the GMC. It was my first true road trip along I-95 — a road I’ve traversed since enough times to circle the globe.
It was a quiet ride, the January scenery filled with skeleton trees and gray skies. Every stop required one layer to be removed, as the weather improved and we began counting signs about Pedro’s home south of the border.
At one stop, I tried to get my grandfather to buy me some road stop widget, but he wasn’t biting.
“You’ve got money,” he said. “You can get whatever you want.”
“But Grandpa, I saved all of that money. I don’t want to waste it.”
So we got back in the truck and he just started talking.
“We saved all of our life for this house in Florida. We put off trips, we didn’t go to faraway places and enjoy every day because we were saving. We traded right now for Lakeland. You can save for a rainy day all you want, but when it comes, all the money in the world may not help the clouds go away.
“Listen to me, spend your money now, enjoy the people you love now. If you need more money, go and get it, but there’s more to life than a big bank account or a retirement house. Don’t be foolish with your money, but don’t be a fool because of it.”
At the next stop, I blew half of my savings on beef jerky that me and my grandfather chewed on all the way to Jacksonville.
I may not have understood everything he said that day, but it’s always stuck with me. And I haven’t saved a penny since.
Travel broadens the mind.
Sitting in an office broadens the ass.
As I am big enough as an ass as it is, and as I generally sit in an office, I think that broadening my mind is manadatory, lest I become a total ass.
I travel to remind myself that life is more than the small town I live in, more than the sterility and cubicle mentality of the U.S. culture and way of life. Life should be about riding atop a train through the Andes and sharing a seat with chickens and pigs on a bus. Travel changes the lens through which I view the world.
Why do I travel? That’s an easy one. I travel so I can return and inhabit my favorite spots in my imagination.
I have a job, a house a kid and a dog. I don’t get out much. Don’t get me wrong, I live in one of most beautiful corners of the world in one of the top five cities (San Francisco, New York, Chicago, New Orleans and my home, Portland, Ore.) in the U.S. I can easily get to any number of world-class outdoor destinations and I take advantage of that as much as anyone with a job, house, kid and dog can.
But getting truly away to the other side of the world doesn’t happen quite as often. Fortunately, I did it when I could and I can go back.
I can return to the balcony of the spare hotel room near the Black Sea in Bulgaria, munching watermelon warm from the sun bought off a farmer’s truck and drinking ridiculously cheap beer from a big brown bottle with no label. The room also had a cracked toiled seat that never failed to pinch your ass, but I tend not go in there.
I can watch the mist swallow the trail behind me as I hike near the Giant’s Causeway in Northern Ireland and contemplate the next pub without having to experience the hangover of the last one.
I can sit in the open-air restaurant outside Malaga and watch the Mediterranean while the waiters, each of them worthy of playing their own version of an Andalucian Frankenstein, pace between the tables hawking whatever seafood is fresh off the grill at the moment, their deep bellows echoing toward the beach: “Sardineta! Camarónes!”
I can wander through the Adjame market in Abidjan buzzing from a stiff cup of strong Senagalese-style coffee, looking for the most outrageous fabrics and lamely trying to bargain with smiling but pushy vendors.
And I can ride on the back of a motorcycle along the Florida Keys without experiencing the sore muscles and pretend it’s as romantic as it sounds.
Trust me, after reading the same preschool bedtime books 100 times in a row, it helps to have spots like this to visit — even if it’s just in the mind.