3 Weird 'Ah-Ha' Moments That Drew Me to Special Occasion Vacations
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 is a priceless gift.
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 peacock launched an amazing adventure.
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.
Treasured Memories
After experiencing the freedom and luxury of villa living compared to cramped hotel rooms, there was no turning back.
Over the last two decades, I’ve been blessed to visit 5 continents—planning special occasion trips to beautiful homes in stunning locations from Agrigento to the Azores, Greece to the Galapagos. Each destination has taught me the value of using local experts when traveling overseas.
As word spread about our family adventures, friends and relatives began asking for help planning their own special events – family roots and legacy trips, milestone birthdays/anniversaries, college friends’ reunions, etc. What began as casual recommendations among friends has blossomed into this website — the done-for-you service I wish existed when I started planning multi-generational trips 25 years 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."
It would be an honor for me to play a part in your trip that “never really ends.” I’m happy to share my 25+ years’ experience. Learn more here.
You also may enjoy The Ultimate Villa Rental Checklist, which shows how to safely navigate the villa rental process and ensure a perfect stay. Whether you work with us or not, I think you’ll find it useful.