Crossing a travel threshold is less about the pins on the map and more about the accumulation of moments and memories along the way. I set my goal of visiting 100 countries and every continent on the eve of Y2K when no one knew whether the world would end or if the entire grid would collapse. At that point, I had only traveled around Florida and the Caribbean on the occasional family road trip or cruise.
At first, everything feels monumental. The first stamp, the first long-haul flight, the first time you realize you are adventuring alone somewhere unfamiliar. Along the way, the world starts feeling smaller, more connected. Adventure looks different depending on the season of life. Early on, it was about distance and difficulty, chasing the next horizon simply because it was there. Later, it became much more nuanced. Agreeing to a stranger’s dinner invitation in Belize. Learning how to navigate Morocco’s medinas without a map. Trusting instinct in places where language falls away.
There were times I almost didn’t make it out alive. Like when my catamaran drifted off into the Caribbean at sunset without anyone noticing. As the sun sank and night fell, the current kept pulling me further and further into the open ocean, as circling shark fins glistened in the moonlight. When I was rescued the next day, I was emaciated, sunburnt and dehydrated. But I was alive, and longing for my next adventure. Many years later, I decided to overcome my fear of heights with a hot-air ballon ride, only to come crashing down in The Everglades shortly after takeoff in a fiery spiral, dodging gators, snakes and who knows what else on the trek back to civilization.
But there were many magical moments, too. Like when I proposed to my wife in India after a whirlwind trip through the Golden Triangle (she said YES!); a private midnight tour of Machu Picchu with one of the world’s most renowned archeologists; heart-racing close encounters with the Big 5 on safari in Africa; culinary adventures throughout Europe; experiencing the soul-soothing vibration of a soprano’s song at the iconic Syndey Opera House; or, most recently, celebrating New Year’s Eve with a Champagne toast over Antarctica on an expedition flight.
Reaching a travel milestone brings gratitude, not closure. Gratitude for the privilege of movement. For the kindness of strangers who become guides, translators and friends. What travel ultimately offers is perspective. You stop assuming there is a single right way to live. You start asking better questions. You learn when to observe and when to participate.
Maps keep changing. Favorites evolve. Curiosity sharpens. The real achievement isn’t found in passport stamps or social media posts. It’s about becoming someone who moves through the world with a sense that there is always more to learn. It’s the way the world now feels like a conversation I get to keep having, one country, one meal, one unexpected moment at a time. And that’s a gift that no souvenir could ever match.
