Why the perfect family vacation is cheaper than you think

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One of the best vacations I’ve ever had was not somewhere exotic. It did not involve air travel, fancy hotels or five-star meals. Instead, it was a road trip my parents, two younger brothers and I took more than 50 years ago to St. Petersburg, Fla., in a monstrous green beast of a car, a 1967 Chevrolet Impala, we called the “Hulk.”

The adventure began with the 20-plus hour drive from Waterloo, Ont., with each of us kids laying claim to our own “personal” space – my little brother on the floor, with two pillows to cushion the “hump”; and my other sibling and I each zealously guarding our respective halves of the back seat. We played Eye Spy, read Archie and Marvel comic books, bickered, ate snacks my mom packed in a cooler, and every half-hour asked, “Are we there yet?” – which ended when my dad pulled over and threatened to leave us on the side of the road.

We had one stopover – a huge win because it had a heated pool and colour TV – before we finally reached what we thought was heaven on earth – a family-run motel, right on the Gulf Coast, with a beach that stretched for miles. Except for one theme park visit, we did nothing but swim, play in the sand, eat ice cream with every meal, and rediscover that, as a family, we liked one another – a lot.

I still smile when I think about that trip – all those long, lazy days. In the years since, I’ve been fortunate to have many amazing travel experiences – to Europe and elsewhere in the world – but for some reason, that simple Florida vacation stands out. Which got me thinking … what is it about certain holidays that makes them so memorable? And, even more important, how do we recreate them so that our own children have vacation memories that will last a lifetime too?

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Toronto travel adviser Julia Hayhurst believes it comes down to a few key things. “The best childhood memories are all about simplicity, ease and repetition, especially when the kids are really young. They love it when there is a sense of safety and security, and of course just being together with family and friends. Even going to the same places every year with the same people. I think that sameness and annual traditions they can count on are probably what makes them happiest.”

Hayhurst is founder of Hayven Travel, a company that specializes in bespoke trips for multi-generational families and groups of friends. In the last decade she has planned hundreds of vacations within Canada and around the world for parents who hope to share unforgettable travel experiences with their children. The best way to ensure that happens, she says, is to follow this cheat sheet: Leave time for spontaneity; be curious; maintain a sense of humour; don’t sweat the small stuff; and never assume spending oodles of money will guarantee a stellar family holiday. Indeed, a study from the University of Texas and the vacation rental firm HomeAway (now part of Vrbo) found the price tag of a vacation had zero effect on its memorability regardless of whether travellers spent $100 or $5,000.

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Instead of planning big, extravagant vacations, Hayhurst recommends giving serious thought to what you want your summer family traditions to be. “What touch points do you want your kids to remember when they’re grown? What experiences will imprint?” Growing up she says her parents took her and her siblings every March Break to Cocoa Beach in Florida with their grandparents, aunts, uncles and cousins.

“My favourite tradition was nightly games of 31 – a card game involving quarters. I started playing on my grandfather’s lap and eventually grew old enough to have my own hand of cards. The joy of winning a pot full of quarters was immeasurable and the chance of success brought us back each night. To this day, 31 remains a strong vacation tradition and my kids learned just as I did – on their grandfather’s lap.”

Jennifer Kolari, a child and family therapist, says one of the best family holidays she’s had was to Europe a few years ago with her husband, teenaged children and 80-year-old dad. The theme of the trip was ‘things go right when they go wrong” – meaning sometimes it’s the mini-disasters and unplanned detours that make a family vacation memorable.

“I’m not sure what it was about that particular holiday, but it just had this kind of magic energy around it – and all of us felt the same way,” says Kolari, founder of Connected Parenting, a company based in Toronto and San Diego that helps parents build emotional resilience in children. “When things didn’t turn out exactly the way we planned, instead of getting stressed, we valued the adventure in it.”

One night, Kolari and family got off a train in Switzerland at midnight, only to realize their hotel was at the top of a steep hill they’d have to navigate with suitcases. “We were all tired, a little grumpy, but rather than get upset we found the humour in the situation. We laughed and laughed – and we still laugh about it today. It’s these little jewels – these little vignettes of pure happenstance – that can make a trip most special.”

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The best holidays, she adds, are an artful combination of some planned activities with ample room for downtime. In other words, plan – but don’t overplan. “If you go, go, go – and the kids get burned out – that won’t be pretty,” Kolari says. It is also equally important to be flexible and willing to adjust your expectations.

The biggest mistake parents make is they set the bar too high. They want everything to be perfect and that is not realistic.”

Linda Montemarano, a luxury travel adviser with Toronto’s First in Service Travel, says her best advice is to let kids be part of the planning process. “Before a trip, we ask our kids, who are now 17 and 19, to pick a couple of restaurants they want to try, and research specific places they want to visit. I have one child, for example, who is really into sports cars so on a trip to Italy my son chose the Enzo Ferrari Museum in Modena while my daughter chose an art gallery. Being part of the planning process enriched the travel experience for both of them.”

Hayhurst says one of the things she loves most about family travel is that she gets to hang up her usual parenting hats – chef, chauffeur, maid etc. – and connect with her kids on a completely different level. “With the hustle and bustle of daily life on pause, I can relax and say ‘yes’ to more things. ‘Yes’ to ice cream for breakfast, ‘yes’ to staying up past bedtime, and ‘yes’ to a few less showers. Why not? Vacations are short and kids find such joy in being allowed to do things a little differently on holiday.

“We live in such a rushed society – we rush to school, we rush home, we rush to make dinner. Just being able to relax into your day without having to be somewhere is such a gift on a vacation.”