Take Your Family on Vacation (And Pay for It, Too)

Want more family time? Consider taking your kids and grandkids on an all-expenses-paid trip.


It’s not easy getting Tobi Asmoucha’s family together. The 49-year-old photographer lives in Vancouver with her mother, while one of her brothers lives in Toronto and the other in London, England. She only gets to see her nieces and nephews – ranging in age from 8 to 19 – on special occasions, like bar mitzvahs. She wishes she could see everyone more often, she says.

Four years ago, her mother, also wanting more family togetherness, decided to do something about the distance. She paid for Asmoucha and her other children and grandchildren, 13 in all, to vacation at an all-inclusive resort in Jamaica, where they spent a week with each other. This past summer, she took everyone on an Alaskan cruise.

While it was a pricey trip for her mother, the family time was worth the cost. “When you go away together, you get that unbroken time,” says Asmoucha. “It’s really nice.”

Asmoucha’s mother is by no means the only parent taking their family on all-expenses-paid vacations. In fact, Lise Coghlan, a travel agent in Kingston, Ontario, with Merit Travel, is seeing more and more boomers and retirees spending some of the money they’ve saved on big family trips. It’s a great way for parents, siblings and grandchildren to connect and build a relationship.

All-inclusive resorts and cruises are a great way to let everybody have their own space, but also do things together, like hang out at the pool or eat meals.

“A lot of families live apart,” says Coghlan. “People these days have big careers, and they might also have kids, so getting together for a family holiday works well.”

However, planning a vacation for multiple families – and multiple generations – isn’t the same thing as taking your young kids on a trip, like you may have used to. Here’s how to make the most out of travelling with your extended family.

Have a home base
Sure, you might like the idea of a cultural tour through Europe, but being on the move can be disruptive to families with young kids. Instead, book a villa, complete with a housekeeper and cleaner, and use it as your home base. That way, some people can go off and see the sights, while others can stay by the pool or enjoy an afternoon nap. As the grandchildren get older, you could consider sending them on an adventure or volunteering tour geared toward kids.

Go all-in
All-inclusive resorts and cruises are a great way to let everybody have their own space, but also do things together, like hang out at the pool or eat meals. Look for one with a kids’ club, so you have the option of dropping the little ones off for a day (or five!) to do crafts or play games. “If the kids are happy, then the parents can really relax. And parents with younger children want that break so they can reconnect with their own family as well,” says Coghlan. Be sure to ask for adjoining or neighbouring rooms so you’re not trekking across the resort – or hiking to different floors of a cruise ship – to find your family members.

Make a special memory
Consider going zip-lining as a group, or taking a van to a city or historical site for the day. When booking excursions or tours, ask for a private van and guide just for your group, says Coghlan, adding that if you book with a travel agent, this can be arranged for you in advance. Coghlan also recommends booking a special dinner at the resort where you’re seated outside, or hiring a photographer to hang out with the family for a few hours to get some photographs out of the trip.

Do your own thing, but have time together
Just because you’re vacationing together doesn’t mean you need to be together all the time. Don’t be afraid to split off into groups or spend time with just your own immediate family for a bit. “I loved going to high tea on the cruise, so whoever wanted to come with me would come,” says Asmoucha. “Some people would go to the gym together.” They did, however, make a point of eating dinner together every night.

Vacationing with the extended family is a great way for cousins to bond, for grandchildren to get to know their grandparents and for busy families to get a break from their lives and spend some quality time together. The biggest problem might be that once you start, you’ll never want to stop. “When people do this, it’s usually the start of a new tradition,” says Coghlan.

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