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Sibling rivalries. Personality clashes. Dubious motels. Tents. Faulty GPS systems. Engine trouble. Puke.

"Are we there yet?"

Road trips are inherently painful, a crash course in your family's survival skills. Somehow, people still become nostalgic for them – from the safe distance of many years.

In the thick of my hormone-soaked adolescence, the Bielski family would drive eastbound from Toronto to places like Mont Tremblant, Quebec City, Gaspé and Cape Breton. With a love of maps but no driver's licence, mom was navigator; dad drove. When my twin brother and I got annoying, "We'd roll the windows down and just let you scream," Dad recalls. "You'd get exhausted and then shut up."

Other tactics included word games, books on cassette (!), gorging at McDonald's and subsequent food comas. During one trip we enjoyed an inexplicable pit stop at the Auberge Grand-Mère hotel – ground zero of what would later become Shawinigate. The aging, wallpapered hotel sat next to a sulphur-reeking pulp mill. The only amusement for a tween (that I could see) was a rock formation that vaguely resembled an old hag – grand-mère herself.

Another road trip saw my father and me making the long trek to Prince Edward Island with my grandmother. In from Poland, Babcia is an avid Anne of Green Gables fan who also suffers from acute verbal diarrhea. In PEI, a hurricane offshoot hit our campground. Our tent flapped up and down, smashing into our faces as we huddled inside, but Babcia's chatter did not relent.

"Road trips have inherent downsides – people throwing up, bad hotels, children fighting in the back seat – but the odd thing is that as people grow into adults, they remember this with fondness. Those difficulties are put into a sentimental context of family memory," says Susan Sessions Rugh, a history professor at Brigham Young University in Provo, Utah, who wrote the book Are We There Yet?The Golden Age of American Family Vacations.

"Maybe it's a little bit like childbirth. If you remembered exactly how painful it was, you'd probably never do it more than once," says Curtis Gillespie, Edmonton author of Almost There: The Family Vacation, Then and Now.

In 1973, Mr. Gillespie's parents took him and his five siblings on an 8,000-kilometre road trip from Calgary to Mexico City – six weeks in a station wagon. Halfway across the continent, the family decides to start camping. It's the pre-MEC days, and the "80-pole oilskin canvas cave" takes two hours to set up.

Another memory: Mr. Gillespie's mother carefully packs six weeks' worth of comics and puzzles for her six-child brood. But half an hour into the epic drive, Mr. Gillespie ralphs his Froot Loops cereal all over them.

"It's a natural human tendency to just forget the struggle, the boredom and the trauma and just focus on what you got out of it," said Mr. Gillespie, who embarked on his own road trip last week, 10 days through the Okanagan and Idaho, with wife Cathy and daughters Jessica, 17, and Grace, 12. The kids brought their electronics.

"We're all in our own little bubble, watching our own movie, reading our book on our iPad, listening to music on our headphones, playing a videogame. We're all in the same vehicle moving toward the same destination on the same journey but we're not necessarily experiencing the same thing. It's really tricky now to say to kids, 'Hey look at that! Let's stop and look at this!'"

iPads and iPhones aren't the only game changers for the modern-day road trip. The advent of the all-inclusive holiday means families have more options – not necessarily a great thing, says Mr. Gillespie, who argues that you lose the spontaneous detours of days on the road.

"These all-inclusives and cruises are predicated on everybody experiencing the same thing: You all have the same buffet food, the same three beaches, the same four bars, the same big giant pool. It's one thing that's been pre-experienced and pre-digested. You know exactly what you're going to get – there are no surprises."

As native south Californians, Prof. Rugh and her husband have made road trips to Disneyland de rigueur for their eight grandchildren, even though it's a 12-hour drive from Utah.

"In the middle, we stop at In-N-Out Burger, one of these intervals we just look forward to. We love road trips."