Because it’s better together
Multi-generation travel creates connections that aren’t possible during brief holiday visits or Sunday dinners. When families share adventures—like discovering a hidden gelato shop in Rome or watching grandkids build their first sandcastle—they forge lasting bonds.
Away from daily distractions, generations truly connect. Grandparents share stories while teaching card games, siblings and cousins form deeper friendships, and parents see their own parents differently. These shared experiences become the stories families tell for years to come.
Sharing new discoveries and the joy of Multi-Gen Travel
TravelVillaGuide aims to inspire you with practical advice and insider recommendations. We cover destination guides, villa selections, and family-friendly activities for all generations. Whether you’re at the idea stage or need hands-on help, let TravelVillaGuide be your trusted partner in crafting unforgettable travel experiences for your extended family.
The greatest gift I can give you
In an age where screens dominate our lives, what do we truly crave?
Experiences that move us. Moments that awaken our senses. Connections that make us feel alive.
Travel offers this escape from the digital world, a rekindling of our innate sense of wonder.
Think how you felt the first time you saw the Cliffs of Moher . . . the Great Barrier Reef . . . the Sistine Chapel.
Remember the awe of witnessing a sunrise over Haleakalā. Or the way the world seemed to pause as the sun set over the Venice Canal.
These aren’t just pretty views. They’re moments that jolt us out of our routines, reminding us of the vast, beautiful world beyond our electronic devices.
Can you recall the surge of adrenaline the first time you rode a horse . . . ran the rapids . . . or watched a humpback whale breach the surface?
New experiences engage all our senses, grounding us in the present in a way no virtual reality ever could.
And then there are those wonderfully unexpected moments:
Swimming with sea lions in the Galapagos. Singing karaoke with locals in a Brisbane dive bar. Taking a night stroll in Tuscany and stumbling upon a full orchestra and chorus performing Carmina Burana in the town square.
These are the memories that nourish us, the stories we tell for years.
And how much richer they are when shared with those we love.
Is there a better gift than seeing your grandchild’s eyes light up at their first elephant sighting? Or watching your partner rediscover their sense of adventure?
In a world of endless scrolling and distant connections, travel offers something real and corporeal: tangible, honest-to-goodness, mind-expanding EXPERIENCES.
And priceless memories that last a lifetime.
This is the gift I hope to give to you.
Not just a trip, but a forever moment.
And a chance to feel something very special:
Truly alive.
Happy travels!
3 Ah-Ha Moments: My Path to Multi-Gen Travel and Villa Vacations
It started with Mickey Mouse.
My parents invited my two sisters and me, our spouses, and all the grandkids to the Magic Kingdom for five days.
My youngest daughter was less than a year old. I remember my father sitting on a bench in Frontierland, bouncing her on his knee after a feeding.
She promptly threw up on him.
Aside from the dyspepsia, it was an epic trip. We still reminisce about it.
That was my first multigenerational trip and my first ah-ha moment. Getting three generations of your family together for a shared experience is a priceless gift.
Ah-ha Moment #2
For our 10th anniversary, my wife and I went to Italy. We visited Rome and Florence and ended in Tuscany, staying in a former papal retreat in Pievescola. Twenty-five years later, we’re still talking about the food and pampering.
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.”
Living in that villa was a real eye-opener. 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
Once I saw the advantages of a villa stay over a cramped hotel room, 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.
Along the way, friends and relatives started asking for help with their multi-generational family trips. What started as casual recommendations has evolved into this website.
One thing I’ve noticed in helping others with their multi-gen trips:
I get more satisfaction helping other families plan their trips than even my own. I’m anticipating the thrills and surprises that await you, the fun you’ll have, and how these shared experiences will bring your family closer.
Because there’s nothing better than sharing special moments with the people you love most.
Happy travels!
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