From overpacking suitcases to returning to the same spot every year, these classic boomer vacation habits leave younger generations shaking their heads — and sometimes laughing out loud.
Every generation has its own way of traveling.
For boomers, vacations are rooted in certain traditions — rituals that feel completely normal to them but leave younger generations scratching their heads.
These habits often come from a mix of nostalgia, upbringing, and a deep sense of what a “proper” vacation should look like.
But as travel styles evolve, what once felt like common sense can now seem outdated or even a little over the top.
To younger travelers, these boomer vacation traditions can feel unnecessarily complicated, expensive, or just plain funny.
Here are eight classic upper-middle-class boomer vacation rituals that younger generations tend to find, well, a bit ridiculous.
1. Lugging around enormous amounts of luggage
For many boomers, packing light is practically unthinkable.
They prefer to bring everything they might need — and then some.
Multiple checked bags, garment bags, and even a separate tote just for shoes are all part of the norm.
You’ll often see them at the airport with a mountain of luggage that looks like they’re moving to another country rather than taking a two-week trip.
Younger generations, who favor budget airlines and minimalism, find this baffling.
They prefer to fit everything into a single carry-on, seeing it as both practical and freeing.
To them, hauling around multiple heavy suitcases isn’t just exhausting — it’s completely unnecessary.
Boomers, however, see it as being prepared and ensuring they have the right outfit for every possible situation.
It’s a clash of priorities: comfort through abundance versus freedom through simplicity.
2. Insisting on rigid itineraries planned down to the minute
Boomers love a good itinerary — often a printed one, complete with maps, confirmation numbers, and color-coded schedules.
To them, a vacation isn’t truly successful unless every hour is planned and accounted for.
Breakfast at 8:00 a.m., museum tour at 10:15, lunch reservation at 12:30, followed by a guided excursion at exactly 2:00 p.m.
Younger travelers, on the other hand, tend to prefer flexibility and spontaneity.
They like the idea of wandering a new city, stumbling upon a hidden café, or changing plans at the last minute based on mood or weather.
To them, boomers’ hyper-structured schedules feel restrictive and stressful.
What boomers see as efficient, younger generations view as vacation overkill.
It becomes less about experiencing the destination and more about ticking boxes off a carefully curated list.
Sometimes, the best memories come from the moments you don’t plan — a concept boomers often struggle to embrace.
3. Booking luxury resorts for “authentic” cultural experiences
Many boomers love to talk about immersing themselves in local culture.
But often, their idea of “authentic travel” involves staying in a five-star resort with every possible amenity.
They’ll rave about experiencing the “real” Mexico while never stepping foot outside their all-inclusive beach property.
To younger generations, this feels contradictory — like claiming you’ve explored Paris when you only saw the view from your hotel balcony.
Boomers see it differently.
For them, comfort and security are top priorities, and a resort represents a safe, hassle-free way to experience a new place.
Younger travelers are more likely to choose hostels, Airbnbs, or boutique hotels that feel connected to local neighborhoods.
While boomers value luxury, younger generations value immersion — and often at a fraction of the cost.
The disconnect leads to plenty of eye-rolling and gentle teasing.
4. Taking endless posed group photos
Boomers love a good photo session, and vacations are prime time for capturing memories — meticulously.
They’ll spend long stretches of time gathering everyone together, posing in front of landmarks, and taking dozens of shots “just in case.”
Younger generations find this exhausting, preferring more candid, natural snapshots taken in the moment.
For boomers, the process itself is part of the fun.
They want perfectly documented proof of the trip, often to share in family albums or framed displays back home.
Younger travelers, accustomed to instant sharing on social media, tend to care more about storytelling than picture-perfect documentation.
To them, standing in line for 20 minutes to take a posed photo feels like wasted time.
To boomers, it’s a non-negotiable tradition — and a key part of the vacation experience.
The clash often leads to some tense but ultimately funny family moments.
5. Packing entire coolers of food for road trips
For boomers, part of vacation prep includes stocking up on snacks and homemade meals before hitting the road.
It’s not unusual for them to pack a full cooler with sandwiches, drinks, and enough snacks to feed an army.
To younger generations, this habit seems excessive — especially when rest stops and restaurants are plentiful along the way.
Boomers see it as practical and budget-friendly, a way to avoid overpriced highway food and save time.
It also comes from a mindset of preparedness that was ingrained during their upbringing.
Younger travelers, who are used to grabbing food on the go with a quick app order, don’t see the need.
They view the cooler as unnecessary bulk that takes up precious car space.
Still, there’s something undeniably nostalgic about stopping at a scenic overlook to eat sandwiches packed at home.
Even if it’s a little outdated, it’s a tradition that speaks to a different era of travel.
6. Treating duty-free shopping like an event
Boomers often treat airport duty-free shops as a key part of the vacation experience.
They’ll browse perfumes, liquors, and chocolates as if they’re in a luxury department store.
Even if the prices aren’t particularly special, the act of buying something “duty-free” feels like a travel ritual.
Younger generations, who are used to online shopping and endless price comparisons, don’t quite get the appeal.
To them, duty-free shops are just another store — often more expensive than the local shops outside the airport.
Boomers see it as part of the fun, a way to bring home gifts and souvenirs with an air of exclusivity.
It’s a tradition rooted in a time when international travel felt rare and glamorous.
For younger travelers, it’s just another overpriced stop between security and the gate.
The generational gap here is clear — and sometimes hilarious.
7. Over-documenting every single moment
It’s one thing to take vacation photos.
It’s another to record everything.
Boomers often love to capture hours of footage — entire meals, long stretches of walking tours, even strangers who happen to be nearby.
They return home with hundreds of photos and video clips, most of which no one will ever see again.
Younger generations prefer to document more selectively, sharing just a few highlights.
To them, constantly taking photos takes away from actually experiencing the trip.
Boomers, however, see documenting as part of the joy.
They love reliving vacations through slideshows, scrapbooks, and framed prints.
What younger travelers see as overkill, boomers see as preserving priceless memories.
It’s a difference in priorities — and a source of ongoing vacation debates.
8. Returning to the exact same destination every year
Perhaps the most classic boomer vacation habit is returning to the same place year after year.
Whether it’s the same beach house, mountain cabin, or resort, this tradition runs deep.
Boomers see it as comforting and familiar, a way to build memories and traditions with family.
Younger generations often crave variety and adventure.
They want to explore new cities, try different cuisines, and collect unique experiences.
To them, going back to the same spot repeatedly feels boring or even wasteful.
Boomers, however, value the predictability and connection that come from knowing a place inside and out.
It’s less about novelty and more about tradition.
While younger travelers might roll their eyes, there’s something sweet about the loyalty boomers have to their favorite spots — even if it does seem repetitive.
Closing reflection: two different visions of travel
Boomers and younger generations approach vacations with completely different priorities.
Boomers lean on tradition, comfort, and a sense of ritual.
Younger travelers favor flexibility, novelty, and minimalism.
Neither approach is wrong — they simply reflect different ways of seeing the world.
While younger generations may laugh at some of these habits, many of them are rooted in values like preparedness, connection, and family time.
And who knows?
One day, today’s “ridiculous” habits might become cherished traditions for future generations.
Because in the end, travel isn’t about who’s right or wrong — it’s about making memories that last a lifetime.
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