3 Weird “Ah-Ha” Moments That Changed the Way I Think About Travel
It all began with a mouse.
When my parents invited the whole family—my two sisters and me, our spouses, and all the grandkids—to the Magic Kingdom for five days, I didn’t realize it would change how I thought about family travel forever.
My youngest daughter wasn’t even walking yet. There’s a moment I’ll never forget: my father sitting on a bench in Frontierland, proudly bouncing his youngest grandchild on his knee after a feeding.
She promptly threw up on him.
Despite that memorable mishap, it was an epic trip that we still laugh about today.
That was my first ah-ha moment.
Getting three generations of your family together for a shared experience isn’t just fun—
it’s rare.
And it’s valuable in a way that’s hard to describe until you experience it.
Ah-ha Moment #2: The Horny Peacock
Our 10th anniversary took my wife and I to Toscana, Italy. We stayed in La Suvera, a former papal retreat with incredible food and 5-star service.
Early one morning, we were startled awake by the earsplitting screeches of a male peacock in pursuit of a mate. The object of his desire was uninterested, which caused him to shriek forte fortissimo! Wide awake, heart racing at 140 bpm, I decided to scout some sunrise photos.
While walking the grounds, I met a friendly American. Turns out, his wife owned a travel company. We started chatting and long story short, my wife ended up working for her, allowing us to travel the world and write about it.
That was my second ah-ha moment.
Travel has a way of creating unexpected moments—
some that stay with you for a long time.
Ah-ha Moment #3: A Father-in-Law’s Wisdom
“I’ve been thinking,” said my father-in-law. He was approaching his 80th birthday at the time. “I believe gifting experiences and memories is better than gifting money. I’ll agree to a birthday party trip under one condition: I’d like us to all stay together under one roof to maximize our time together.”
That villa changed everything. More space, freedom, privacy, control, amenities, activity choices, and a private pool. A kitchen and dining room for sharing meals around a common table. All for less money than separate hotel rooms.
It gave us a sweet family memory we often reminisce about during the holidays.
That was my third ah-ha moment.
Where you stay doesn’t just affect comfort—
it shapes how you spend your time.
Staying together under one roof changed everything.
Meals happened naturally.
People gathered without planning.
Time together wasn’t something we had to coordinate—
it just happened.
And that’s what made the experience feel different.
More connected.
More present.
And, in a very real way…
more meaningful – and more enjoyable for everyone.
Looking back, those three moments all pointed to the same idea.
The trips that matter most aren’t defined by the destination.
They’re defined by the time you spend together.
Because that’s what stays with you.
The conversations.
The shared experiences.
The moments you didn’t plan.
That’s what makes it meaningful.
Treasured Memories
After experiencing this shift—from planning trips around places to designing them around time together—there was no turning back.
Over the last 25 years, I’ve traveled across five continents, planning meaningful group trips everywhere from Greece and the Galapagos to Sicily and the Azores. Along the way, I learned the value of local expertise—and how the best trips aren’t just about where you go, but how the experience brings people together.
As friends and family began asking for help planning their own reunions, milestone celebrations, and legacy trips, what started as casual recommendations evolved into Travel Villa Guide: the done-for-you service I wish existed when I began planning multi-generational trips decades ago.
"Travel is like love… it’s a heightened state of awareness, in which we are mindful, receptive, undimmed by familiarity and ready to be transformed. That is why the best trips, like the best love affairs, never really end."
If you’re thinking about bringing your people together for something like this—
I’d be happy to help you make it happen. Learn more here.
You also may enjoy the 3-Step Guide, The Gift of Time Together. Whether you work with us or not, I think you’ll find it useful.