Why do boomers treat a five-day beach trip like they're preparing for an Arctic expedition while millennials pack a carry-on and call it done?
Ever notice how your parents or older relatives approach vacation planning like it's a military operation? Meanwhile, you're over here booking an Airbnb the night before and calling it spontaneous adventure?
I've spent enough time observing travel patterns across generations to know that boomers have their own unique vacation playbook. And honestly, some of their traditions leave younger travelers scratching their heads in confusion.
These aren't necessarily bad habits. In fact, some of them have merit. But they do highlight just how differently generations approach the art of taking a break. Let's explore some of the quirks that keep showing up in boomer travel itineraries.
1. Printed confirmation pages for everything
Walk into any boomer's house a week before vacation and you'll find a neat stack of papers on the kitchen counter. Hotel confirmations. Flight itineraries. Car rental receipts. Restaurant reservations. All printed, highlighted, and organized in a color-coded folder.
I get it. There's something reassuring about having a physical backup. But younger travelers are perfectly content with screenshots and email confirmations stored on their phones.
The thing is, boomers grew up in an era where if you didn't have that printed ticket, you weren't getting on the plane. Old habits die hard. They've seen technology fail enough times to know that batteries die and Wi-Fi disappears at the worst possible moments.
Still, watching someone pull out a three-ring binder at airport check-in does feel like a throwback to another era.
2. Booking through travel agents
Remember travel agents? Boomers sure do. And many of them still use them.
While millennials and Gen Z are comparing flight prices across seven different apps, boomers are calling Linda at the travel agency they've been using since 1987. She knows their preferences, handles all the details, and sends them a complete itinerary packet.
There's actually something nice about this approach. Travel agents have made a comeback in recent years because they handle the overwhelming number of choices and options available today.
But to younger travelers who've never known a world without Expedia and Booking.com, paying someone to book your trip feels unnecessary. Why would you hand over that control when you can do it yourself in minutes?
3. Arriving at the airport three hours early for domestic flights
This one drives me absolutely bonkers when I travel with my parents.
Boomers will insist on leaving for the airport at dawn for a noon flight. They want time to park, check bags, grab coffee, browse the terminal shops, and settle in at the gate with a good two hours to spare.
Younger travelers? We're the ones sprinting through security forty minutes before boarding, shoes in hand, laptop still in the bag because we paid for TSA PreCheck specifically to avoid this chaos.
The difference comes down to risk tolerance. Boomers remember when air travel was unpredictable and arriving early was genuinely necessary. Now, with mobile boarding passes and streamlined security, you can cut it much closer. But try convincing someone who missed a flight in 1994 because of a long check-in line that times have changed.
4. Sending physical postcards
Picture this. You're on a beautiful beach somewhere tropical. The sun is setting. The water is crystal clear. And your boomer travel companion is hunched over a table writing postcards to fifteen different relatives.
They'll spend vacation time hunting down postcard vendors, buying international stamps, and finding mailboxes. Meanwhile, younger travelers posted seventeen Instagram stories and a TikTok video before lunch.
I'll admit there's something charming about receiving a postcard in the mail. It's tangible. It's thoughtful. It shows someone was thinking about you enough to put pen to paper and navigate a foreign postal system.
But it's also wildly inefficient in an age where you can share your entire vacation experience in real time with everyone you know simultaneously.
5. Eating dinner at 5:00 PM sharp
Nothing says boomer vacation like showing up at a restaurant when they're still setting up for the dinner rush.
I once traveled to Spain with an older couple who were genuinely distressed that restaurants didn't open for dinner until 8:00 PM. They couldn't understand why anyone would eat so late. The cultural norm of dining at 10:00 PM? Absolutely baffling to them.
This stems from lifelong routines that are hard to break, even on vacation. Boomers grew up with structured meal times and they stick to them religiously. Early bird specials exist for a reason.
Younger travelers tend to be more flexible. We'll eat when we're hungry, which might be 3:00 PM or 11:00 PM depending on what we're doing. Schedules feel restrictive when you're supposed to be relaxing.
6. Taking bus tours of major cities
Hop-on, hop-off bus tours are boomer catnip. They love them. Every major city, same routine: buy the two-day pass, ride the entire loop, listen to the audio guide, and hop off at exactly three predetermined stops.
Younger travelers would rather walk, bike, or use public transportation to explore. We want to stumble upon hidden cafes and wander down random side streets. A bus tour feels too structured and touristy.
But here's the thing. Those bus tours are actually brilliant for getting your bearings in a new city. They're efficient, informative, and you can cover a lot of ground quickly. Guided bus tours remain popular because they provide context and historical information that you might miss exploring on your own.
Still, there's no denying that a bus full of people with cameras and sun visors doesn't exactly scream adventurous traveler.
7. Refusing to use ride-sharing apps
I've watched boomers stand in taxi lines for thirty minutes rather than open Uber or Lyft on their phones. The resistance is real.
Part of it is trust. Getting into a stranger's personal car feels inherently riskier than a licensed taxi, even though the data doesn't really support that fear. Part of it is unfamiliarity with the technology. And part of it is loyalty to traditional systems that have always worked fine.
My dad finally downloaded Uber last year after I showed him how it works. He was amazed by the convenience but still refers to it as "one of those app taxis" and seems vaguely uncomfortable with the whole concept.
Younger travelers, meanwhile, can't imagine traveling without ride-sharing apps. We use them everywhere, often because they're cheaper and more convenient than traditional taxis. The thought of waving down a cab on the street feels almost quaint.
8. Over-packing like they're moving permanently
Boomers pack for every possible scenario, weather condition, and social situation that might occur during a five-day trip. Multiple outfit options per day. Backup shoes. An entire pharmacy of medications and first-aid supplies. Books, magazines, and newspapers for reading material.
They're checking bags and paying fees without a second thought because traveling light isn't even on their radar.
Younger travelers have turned minimalist packing into an art form. We're the ones doing two weeks in Europe with a carry-on and a personal item. We wear the same three outfits in different combinations and wash clothes in the sink if necessary.
The difference? Boomers want to be prepared for anything. We want to be mobile and flexible. Both approaches have merit, but watching someone struggle with three suitcases through a cobblestone street does make you question their strategy.
9. Collecting physical maps and guidebooks
Stop into any visitor center and you'll find boomers loading up on free maps, brochures, and attraction guides. They'll spread them across hotel beds, highlight routes, and dog-ear pages of recommended restaurants.
It's actually kind of endearing. There's a ritual to it, a tangible way of engaging with a destination that feels more intentional than scrolling through Google Maps.
But younger travelers? We've got GPS in our pockets. Why would we need a paper map when our phones can navigate us anywhere, show real-time traffic, and suggest nearby attractions all at once?
10. Documenting everything in photo albums
The vacation isn't over until the photos are printed, organized chronologically, and placed in a labeled photo album with handwritten captions.
Boomers will return from a trip and immediately order prints of their favorite shots. They'll spend hours arranging them carefully, writing little notes about where each photo was taken and what was happening at the time. These albums become treasured keepsakes they'll pull out for years.
Younger travelers take hundreds of photos that live forever on phones, cloud storage, or social media. We might share them online, but creating a physical album? That feels like homework.
I'll say this though: there's something special about flipping through an actual photo album that scrolling through iPhone pictures doesn't quite replicate. The physicality of it, the intentionality of choosing which moments to preserve, the ability to hold memories in your hands. It's a slower, more deliberate way of processing experiences.
Final thoughts
Look, I'm not here to say one generation has it all figured out and the other doesn't. The truth is, both approaches have strengths and weaknesses.
Boomers might seem overly cautious and stuck in their ways, but their traditions come from decades of travel experience. They know what works for them. They value preparation, reliability, and having backup plans. Those aren't bad priorities.
Younger travelers prize flexibility, spontaneity, and leveraging technology to make travel easier. We're comfortable with uncertainty and we adapt quickly when plans change. That's not wrong either.
Maybe the best approach is somewhere in the middle. Print the important confirmations but keep digital copies too. Use your phone's GPS but grab a paper map as backup. Book your own flights online but don't be afraid to consult an expert for complex itineraries.
Take what works from both generational playbooks and leave the rest. After all, the goal of vacation is the same regardless of age: to relax, explore, and create memories worth keeping.
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