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The Greenwood Davis family on a multigenerational trip to Jamaica. Travelling with both her parents and her kids has taught the author a few things about her relationship with both generations.Heather Greenwood Davis /The Globe and Mail

“I don’t think that’s a good idea,” I tell my mother as she wanders off the resort property, away from my son and me, in search of a man with a machete who can climb a tree and pick her a fresh coconut in Mexico.

“I don’t think that’s a good idea,” I say to my son, who is preparing to do a running jump off a cliff in Jamaica while my parents cheer from the sidelines.

In both cases, they do it anyway, slipping past me with a smug grin about their success when they’re done, and then heading directly to their supporting cast of co-conspirators for a multigenerational fist bump.

Yup, somewhere along the road between leaving the sphere of my parents’ responsibility and becoming deeply entrenched in parenting my own kids, I became annoying to both.

Such is the life of the sandwich-generation parent: Too responsible to ignore the dangers; not cool enough to avert the eye roll.

I’m not the only one in this precarious position. According to the 2019 Virtuoso Luxe Report, multigenerational family travel is the No. 1 travel trend for 2019. The annual survey looks at current and anticipated bookings across its network of about 17,500 travel advisers in 50 countries. Multigenerational travel also came in second to active or adventure trips as one of the 10 key trends in family travel for 2019.

Still, multigenerational travel can be infuriating at times: How can the parents who once chastised me for running from the living room to my bedroom be encouraging my kids to jump from the top concrete step at a resort?

But it’s also one of the best things we’ve ever done.

Over the years, on trips together in Canada, the United States, the Caribbean, Europe and Mexico, I’ve watched my parents and my kids share moments that feel like emotional candy for me: whispered confessions, shared giggles, wiped tears, early-morning ice cream and late-night swims.

The author's son Ethan and mother, Herma, share a moment on vacation.Heather Greenwood Davis /The Globe and Mail

The funny thing is that these trips – where I’m often both the butt of the joke and the negator of perilous adventures – have almost all been crafted by me.

It’s a common thing. A 2015 survey carried out by AARP found that most multigenerational trips stem from the desire to spend quality time with one another and that the middle generation is most likely the person planning the majority of the trip. And it makes sense, when you think about it: From our vantage point as the filling in the proverbial sandwich, we can see how fast the kids are growing up and how little time we may have left with our own parents. We are the ones who understand the value in the relationships that the generations on either side of us are at risk of losing. These trips offer us a chance to help them see it, too.

I can watch my parents become kids again, playing in the water or running through the fields with their grandchildren as if the aches and pains they complained of earlier no longer exist.

And I’ve watched my kids turn to their grandparents for a sounding board about their mean parents and, in return, gain lessons that a parent can’t always teach.

The beauty of watching her parents and her kids forge strong relationships has been Heather Greenwood Davis's reward for organizing multigenerational trips.Heather Greenwood Davis /The Globe and Mail

I often come away from these trips with something, too. Unexpected moments of insight and opportunities where I can let my guard down and not be their kid, or their mother.

In Mexico, while my son is at a kids’ club, I get quiet time with my mother, where I learn a bit more about her childhood. In Jamaica, as my father takes my youngest around his former high school, I get a rare glimpse of what he would have been like as a teenager.

I get to watch them be the people they can only be in that grandparent-grandchild relationship. The burden I shoulder by monitoring bedtimes or trying to keep us on schedule allows both generations to relax.

Plus, there is no question that the sound of my son giggling or the look on my mother’s face when my kids ask a question I’d never have dared at their age helps to ease the moments when both are annoyed with me.

I know that my time is limited here in this middle seat of their travelling life (according to a 2018 AARP report, skip-generation travel – where the outer sandwich generations ditch the one in the middle – are on the rise.)

But until they kick me out, I’ll be over here in the middle giving them reason to unite against me in places around the globe. And I’ll enjoy watching them do it.

Where to take the bread in your multigenerational sandwich:

Resorts are jumping on the multigenerational trend with offerings that will appeal to all members of the family. Here are three to consider.

  • Las Brisas Huatulco: This Mexican resort offers kids’ clubs for little kids, adventurous sports (including kayaking and a bungee pyramid) for active teens, five different restaurants to choose from (so that even picky eaters have a choice) and mini golf for the family to play together. Plus, rooms in June can be had for as little as US$70 a night.
  • Hyatt Regency Huntington Beach Resort & Spa: This California spot has a new customized collection of specialty suites with configurations that make sure everyone has enough space to relax. Multigenerational family suites boast two- and three-bedroom units that can sleep up to 12 guests each.
  • Nizuc Resort and Spa, Cancun: Away from the Cancun strip in Mexico, this spot has a kids’ club for children aged 4-12, a teen lounge gaming centre, family cooking classes and help with off-site excursions to spots such as Mayan sites Chichen Itza and Tulum. Kids stay, play and eat free with the “3rd Nights the Charm” package (a complimentary third night for every two nights paid) on travel between June 1 and August 31.

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