TORONTO — For multigenerational trips, the grandparents are the key. 

Not the kids – although anyone who’s had to sweet talk young travellers through long lines, or missed meals, or a boring tour (it happens) knows that if the kids aren’t happy, no one is happy.

Pink Palm Travel’s Jennifer Gaskell

Not the parents – even though it’s typically mom or dad who is the first point of contact, the group wrangler and the day-by-day decision-maker.

Building a portfolio of satisfied return multi-gen family clients means getting it right with the grandparents. 

If you’ve booked these trips you know that grandparents are almost always the ones funding the trip. And if the vacation caters to their needs as much as everyone else’s, they’re much more likely to endorse a repeat experience.

Pink Palm Travel’s Jennifer Gaskell books a lot of resort vacations for extended family groups. 

“For many families, life is busy, and they’re looking for quality time together rather than constantly moving from place to place. That’s where a resort is the best fit,” she says.

And when groups include grandparents, parents, teenagers and young children, “everyone has different energy levels, interests and mobility needs.”

Mobility is always one of her first conversations with grandparents in multi-gen groups. Grandparents might be the least likely to articulate their needs. They’re also the most likely to appreciate the small courtesies that can make a big difference.

“I want to know if they require elevator access. If they’ll be comfortable walking the property. And if there are quieter areas of the resort that still provide easy access to restaurants and family activities,” she says.

She also asks about their dietary requirements and medical considerations.

Says Gaskell: “What I hear most often from grandparents is that they want to be close enough to enjoy time with the family, while still having their own space to relax and recharge.”

Multi-gen family travel dreams made real, with CrystalSky 4-Bedroom Reserve Villa accommodation at Treasure Beach at Beaches Turks and Caicos

MULTI-GEN TRIP ADVICE – FROM A BANK?

According to the Family Travel Association, at least in the U.S., 57% of families plan to take a multigenerational trip in the next year, and nearly half plan to include extended family members such as aunts, uncles and cousins.

That statistic comes courtesy of RBC, in an August 2026 blog focused on helping older clients factor big family trip costs into long-term wealth plans. 

Any travel advisor who’s booked a high-value extended family trip – with price tags reaching six figures – won’t be shocked to hear that a banking and investment firm is weighing in with multi-gen travel tips.

Gaskell says her biggest booking ever was Cdn$200,000 for a multi-generational family travelling to Beaches Turks & Caicos.

“The family came to me knowing they wanted the very best experience, and based on my first-hand knowledge of the resort, I recommended the new Treasure Beach because it was the best fit for their family’s priorities, accommodations and overall experience.”

“THESE SIX-FIGURE BOOKINGS OFTEN CLOSE FASTER THAN A $10,000 VACATION”

Sticker shock? Surprisingly, no. 

“I always come to my consultations with an idea of pricing, so clients have a clear understanding of the investment from the very beginning. I also find that today’s travellers have usually done some preliminary research before they contact me, so they already have a sense of what these vacations cost,” she says.

“What I find interesting is that these larger family trips rarely experience sticker shock. Once families have committed to creating these memories together, they’re focused on getting it right. If the ideal room category isn’t available and an upgrade is needed, there’s typically very little resistance.”

She adds: “One thing I’ve found fascinating is that these six-figure bookings often close faster than a $10,000 vacation, often within a day. I believe it’s because the clients know what they want, and they’re looking for expertise. While they could certainly book themselves online, having the peace of mind of a travel agent on top of the file matters to them.”

NOT JUST SECOND BEDROOMS, BUT SECOND BATHROOMS TOO

While the older generation’s needs are crucial, Gaskell makes sure to cater to the younger travellers too. “The ages of the children are also a huge consideration. A family travelling with toddlers may not want a two-hour transfer after their flight, whereas a family with older children may be much more flexible. I also ask about sleeping arrangements. If a family is travelling with young children, I’ll usually recommend a second bedroom. If teenagers are travelling, an additional bathroom often becomes just as important.”

For grandparents, meanwhile, one of the biggest priorities might have nothing to do with the hotel. Gaskell says she’s seen it time and again: “The flight experience. For some grandparents, upgrading to business class is just as important as the resort itself.”

For multi-gen family trips, what works best – a resort, a cruise or a land tour? Watch for more from this series in Travelweek Daily.