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

Our 10th anniversary took my wife and I to Italy, where we explored Rome and Florence before discovering Tuscany. There, we stayed in a former papal retreat in Pievescola. Twenty-five years later, the memories of that luxurious stay — the incredible food, the attentive service — remain vivid.

Early one morning while taking photos, I met a friendly American. His wife owned a travel company. Long story short, my wife ended up working for them, allowing us to travel the world and write about it.

Ah-ha Moment #3

“I’ve been thinking,” said my father-in-law. He was in his late 70s at the time. “I believe gifting experiences and memories is better than gifting money. Let’s plan a family trip. One condition: I’d like us to all stay together under one roof.”

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. That trip is a sweet family memory we reminisce about during the holidays.

Forever Memories

After experiencing the freedom and comfort 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 for fun, food, wine, and wisdom — planning trips around beautiful homes in stunning locations from Cape Town to Cape May, Agrigento to the Azores, Greece to the Galapagos. Each destination has taught me something new about the art of family travel.

As word spread about our successful family adventures, friends and relatives began asking for help planning their own multi-generational trips. What started as casual recommendations among friends has blossomed into this website — your guide to creating unforgettable family memories.

What I’ve discovered is that helping other families plan their perfect getaway brings me even more joy than planning my own trips. I love anticipating the moments of wonder that await you . . . imagining the laughter you’ll share . . . and knowing how these experiences will become treasured memories for years to come.

Because nothing beats sharing a home away from home with the people you love most.

Looking for the perfect villa for your multi-gen vacation? I’m happy to share my 20+ year’s knowledge to help you find the perfect rental your family will love—and fun things to do while you’re there. 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. Don’t rent a villa without it 😉