Every multigenerational trip has a Grandpa situation.
Not always a grandpa, technically. Sometimes it’s an uncle. Sometimes it’s a father-in-law. Sometimes, honestly, it’s just whoever in the group is most committed to the idea that travel is uncomfortable and expensive and ‘we just went somewhere two years ago.’
You know who I mean.
Here’s how to bring them around.
Start with what’s in it for them specifically.
Generic trip excitement does not move the practical traveler. ‘It’ll be so fun!’ is not a compelling argument for someone who defines fun as their own recliner and a predictable dinner schedule.
What works is specifics. If Grandpa loves fishing, you find a trip with a fishing excursion in a place he’s never been and you lead with that. If he’s a history guy, you find the tour that goes deep on WWII history or the ancient ruins or whatever lights him up. If his whole thing is that he doesn’t want to deal with logistics, you tell him that the whole trip is handled and all he has to do is show up at the airport.
Give him a reason that is actually about him, not just about the family wanting him there. (Even though that’s also true.)
Deal with the objections before they become a wall.
The most common ones I hear: it’s too expensive, I don’t want to be on my feet all day, what if I don’t feel well, and I hate flying.
Each of these is solvable. Cruises are remarkably accessible and don’t require a lot of walking if you don’t want to. Travel insurance covers the ‘what if something goes wrong’ fear almost entirely. And flying is often better now than the last time they flew, especially if you let someone else handle the booking and the logistics so they’re not navigating airports alone.
Name the objection out loud before he does. Tell him you’ve already thought about it. Tell him how it’s handled.
Let someone else make the case.
Sometimes the most effective thing you can do is not be the one doing the convincing. If Grandpa has a friend who went on a similar trip and loved it, that friend’s story will do more work than anything you can say. If there’s a grandkid who has been talking about wanting to see Alaska or go on a cruise, let that kid ask.
The emotional leverage shifts completely when it’s his seven-year-old granddaughter asking him to come, versus an adult child presenting a trip itinerary.
I have watched this work more times than I can count.
And if none of that works?
Book the trip. Tell him the dates. Sometimes the best way to get Grandpa on board is to simply make it real and give him something to look forward to. Most skeptics, once they’re actually on the trip, are the ones most reluctant to leave.
If you’re in the middle of planning a multigenerational trip and navigating some family dynamics around it, I’ve heard it all. Reach out and let’s talk through it.
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