What No One Tells You About Multi-Generational Travel

You want to plan a big family trip? Buckle up. This isn’t your average vacation.

If I had a dollar for every family who’s come to me overwhelmed by planning The Big Trip, I’d be writing this from a villa in Tuscany. There’s a reason I plan so many multigenerational vacations—because they’re joyful, chaotic, and anything but simple.

Multigenerational travel isn’t just “pick a destination and go.” It’s multiple origin cities, mismatched flights, strollers and wheelchairs, and mountains of luggage. It’s a toddler who needs snacks every 90 minutes and a grandma who’s more comfortable navigating the airport in a wheelchair. It’s balancing budgets, opinions, allergies, health needs, and motion sickness… All while trying to keep the peace between the museum lovers and the museum avoiders.

And then there’s that uncle who wants to “risk it” with a passport that expires next month. (Spoiler: I’m the bad cop on that one.)

A well-planned multi-gen trip means thinking through every detail: hotel rooms with the right bedding configuration, safe transfers, accessible sightseeing, and the perfect mix of together time and breathing room (IYKYK). It’s coordinating multiple travel insurance policies, keeping track of payments, and making sure everyone feels cared for: from the one-year-old to the seventy-year-old.

But here’s the best part: it’s also the giddy text from a mom saying, “This was the best day of their lives.” It’s the champagne waiting in the room for a 50th anniversary, the wide-eyed grandkids ordering gelato with grandpa in Italian, and the photos that will be shared at family gatherings for years to come.

That’s the magic of a well-planned multigenerational trip. And that’s why I do what I do. I help your family make memories, not migraines.