Category Archives: travel

Flying Solo on Honeymoon Island: Lessons Learned in Traveling Alone

Flying Solo on Honeymoon Island: Lessons Learned in Traveling Alone

I mostly travel alone. Sometimes it is by choice, and sometimes it is simply because I’m not one to let my perpetually single status stop me from doing anything I dream of doing. To be honest, most times I travel solo, I don’t even notice. I’m pretty awesome company (I think), and there are always… more…

Bora Bora or Bust: Why aren’t you getting on the plane?

Bora Bora or Bust: Why aren’t you getting on the plane?

For several years I’ve been helping people learn how to travel for nearly free using points and miles. There’s something amazing about encouraging people to dream about a place they’ve never visited—one that would most likely never be accessible to them if they had to save the money to get there—and then show a few practical tools to make… more…

Roots and Regrets: Travel Lessons from Italy

Roots and Regrets: Travel Lessons from Italy

My first trip to Italy was in 1993. I was a young and hip backpacker, too cool for the universe—as most teenagers are—and especially too cool for my family. Or so I thought. Now that I’m much older and a little wiser I’ve come to realize that this whole time my family is awesome. My… more…

The Paradox of Settling

The Paradox of Settling

“When are you going to settle down?” As a wander of more than 20 years, this is the question I’ve learned to field at least once a week. Friends, family, people I date, random acquaintances, and readers of the internet inquire about my ability to “settle” all of the time. “Settle down?” It’s a simple question, and… more…

5 Lessons from a Half a Life of Travel

5 Lessons from a Half a Life of Travel

It’s official. I’ve now been traveling over half of my life. And I don’t regret it for one minute. Now that I’m twice as wise as I was when I got my first passport stamp on 01/26/93, I thought I’d share a few of the hundreds of lessons I’ve learned from 23 years on the… more…

Get a Head Start on Free Travel in 2016

Get a Head Start on Free Travel in 2016

Another year is wrapping up. If you’re anything like me, you’ve already probably started dreaming of all the adventures ahead in 2016. I’ve got Bhutan, Tibet, Israel, and Italy on my list for next year, and I hope to finish up visiting the rest of the states that have eluded me for many years (Oklahoma,… more…

7 Lessons from 7 Continents: Asia + Worldview

7 Lessons from 7 Continents: Asia + Worldview

A single phrase, commonly heard across Southeast Asia, sums up the biggest lesson that six years on this continent taught me: “Same, same, but different.”  After my first dream trip to Europe and the consequential discovery of travel’s possibility, it didn’t take me long to figure out how to venture even further afield. Within a… more…