The real test of a family trip isn’t the destination—it’s how different generations reveal their quirks when placed outside their comfort zones.
Vacations are supposed to be relaxing. But if you’ve ever traveled with your boomer parents, you know the trip often comes with a side of secondhand embarrassment.
They don’t mean to. It’s just that generational habits, social norms, and different comfort zones play out in very visible ways when you’re in a new place together.
The gap between how boomers approach travel and how their kids want to experience it is bigger than many realize. While younger generations lean into flexibility, subtlety, and “going with the flow,” boomers often bring structure, directness, and habits that don’t always translate well abroad.
Let’s talk about nine of those awkward things boomers do on vacation—the ones their kids notice, cringe at, but rarely call out.
1. Talking way too loud in quiet spaces
Why is it that boomers’ voices automatically jump three notches when they’re in a restaurant or museum?
It’s not just your imagination. As the American Speech‑Language‑Hearing Association explains, age-related hearing loss—known as presbycusis—often reduces clarity, especially in crowded spaces. That leads many to unconsciously raise their volume to be heard.
So there you are, whispering to your sibling, while your parents are basically broadcasting the day’s itinerary to half the café. Kids tense up, scanning the room to see who’s staring. Boomers, meanwhile, are unfazed—completely unaware that their conversational decibel level has turned them into the main attraction.
2. Over-tipping—or under-tipping—in confusing ways
Tipping culture varies wildly from country to country. And while millennials might discreetly Google “how much to tip in Spain,” boomers often go with their gut—or what worked back home.
I once watched a boomer couple in Rome insist on tipping 30% at a trattoria, confusing both the server and their Gen X kids. Another time? A dad left two coins on a table in Paris and strutted out, leaving his mortified daughter scrambling to throw down extra cash.
This isn’t just about money. It’s about cultural sensitivity. As travel psychologist Michael Brein has said, “Every culture has its unspoken codes, and ignoring them—even unintentionally—can cause unnecessary friction.” Kids pick up on that instantly and feel the weight of their parents’ faux pas.
3. Photographing everything with outdated tech
You know that moment when everyone else has their phone out, taking subtle shots, and your boomer parent pulls out a full-sized iPad?
It’s not just the device—it’s the way they stop foot traffic, line up the shot for five minutes, and then wave you into the frame whether you like it or not.
I’ve noted before how the urge to “preserve the moment” can supersede actually living it. Boomers often lean into this instinct deeply. Their kids? They’re trying to blend in—not star in a 12-minute sidewalk photo shoot.
And here’s the kicker: many of those photos end up blurry—or worse, stranded forever in a forgotten camera roll.
Interestingly, research on photo-taking reveals a fascinating downside. Studies show that snapping photos with the intention to share with others—rather than simply capturing for yourself—actually reduces enjoyment of the experience. This shift in focus turns a moment into performance.
4. Complaining loudly about “foreign” food
Most boomers were raised on meat-and-potatoes cooking. When they find themselves in a country where the breakfast doesn’t include bacon or the coffee is smaller than a soup bowl, the comments start flying.
“Why don’t they serve real coffee here?”
“Who eats fish this early in the morning?”
Their kids usually shrink in their seats, wishing their parents would embrace the whole “when in Rome” thing.
To be fair, comfort food is tied to nostalgia. As psychologist Susan Whitbourne notes, “Food is often the most emotionally loaded part of culture—it’s linked to security and identity.”
That explains why boomers can struggle to adjust when confronted with dishes that don’t match their expectations. But the delivery? That’s where it gets awkward.
5. Asking strangers overly personal questions
This one’s almost charming—until it isn’t.
Boomers often see no problem with asking the server where they’re from, how old they are, or whether they like their job. It’s small talk to them. To their kids? It feels invasive and awkward, especially when the stranger clearly doesn’t know how to respond.
I’ve had to sit through exchanges where the poor barista in Lisbon was grilled about their dating life, while I sank lower in my chair. Boomers think they’re connecting. Younger travelers see it as overstepping.
As sociologist Deborah Tannen once noted, “Boomers were raised to value friendliness and connection. Younger generations value boundaries.” That mismatch comes out full force on vacation.
6. Treating service staff like personal guides
Ever notice how some boomers turn hotel clerks into travel agents?
“Where should we eat tonight?”
“What’s the best museum here?”
“Can you book us a cab for tomorrow at 6 a.m.?”
While there’s nothing wrong with asking questions, it’s the expectation—the assumption that staff exist purely to handle every whim—that makes their kids squirm. In an age of TripAdvisor and Google Maps, it feels almost willfully helpless.
I once watched my mom hand a concierge a handwritten list of possible activities and say, “Just tell me which one is best.” Her logic? He was the local, so of course he’d know. My logic? We could have figured it out in 60 seconds on our phones without putting someone on the spot.
7. Hoarding freebies
Buffet rolls, tiny hotel shampoos, airplane peanuts—if it’s “free,” boomers are stuffing it into their bag.
On a recent trip, I watched a dad fold napkins around five croissants “for later,” only for his embarrassed son to mutter, “Dad, we’re not starving.”
It’s a Depression-era hand-me-down instinct. Many boomers were raised by parents who taught them not to waste and to always save for leaner times. But when that mindset shows up in a modern resort with unlimited food, it reads less as resourcefulness and more as awkward over-preparedness.
8. Treating schedules like military operations
Vacations are supposed to have a flow, but boomers often run them like clockwork.
“Breakfast at 7. Museum at 9 sharp. Lunch no later than 12.30.”
If you’ve ever traveled with your boomer parents, you’ve probably been hustled across cobblestone streets because the “next stop” was looming. Kids want to wander. Boomers want to conquer. And that tension often leads to eye rolls and whispered complaints.
There’s a psychological reason for this: structured schedules offer us a sense of control. Studies on stress show that when events are predictable and controllable, their psychological impact diminishes compared to unpredictable stressors.
For boomers, who grew up in more structured times, that preference gets amplified on vacation. For their kids? It’s just exhausting.
9. Making sweeping comparisons to home
Boomers love to compare everything to how it’s “done back home.”
“This would never fly in the States.”
“Back in our day, hotels had real keys.”
“Honestly, our beaches are better.”
They don’t always realize how dismissive it sounds, but their kids do. The unspoken message is: nothing measures up. And when you’re trying to soak in another culture, that commentary can make you want to sink into your chair.
To me, this is the ultimate generational divide: boomers see travel as a yardstick against what they know, while younger travelers often see it as a chance to experience something new without comparison.
The bottom line
Traveling with boomer parents is a lesson in patience—and in understanding generational differences.
They’re not trying to embarrass anyone. They’re just carrying decades of habits into new environments. And sometimes, those habits clash with modern expectations of cultural sensitivity, subtlety, and flexibility.
If you’ve felt the flush of secondhand embarrassment on a family trip, you’re not alone. But maybe the next time it happens, instead of cringing, you’ll laugh a little and remember: vacations aren’t just about the destination. They’re about learning how different generations navigate the same world.
And if nothing else, you’ll come home with stories—awkward, funny, unforgettable stories—that are worth retelling long after the trip is over.
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