For every dead phone and bad Airbnb, there’s a boomer parent somewhere quietly saying, “I told you so.”
Jordan Cooper / Nov 15, 2025
For every dead phone and bad Airbnb, there’s a boomer parent somewhere quietly saying, “I told you so.”
I spent last spring watching my parents plan their annual trip to Sedona, and honestly, I couldn’t figure out what they were doing half the time. Printed maps? A physical travel agent? An itinerary that looked like a military operation?
Fast-forward six months, and I found myself stuck in Porto with a dead phone battery, no idea where my Airbnb was, and a sudden appreciation for why my dad always carries a paper backup of everything.
Turns out, a lot of boomer travel habits that seem completely bizarre to those of us who grew up booking flights on our phones actually have some serious wisdom baked in. Today, we’re exploring nine boomer travel trends that millennials call “weird,” but make way more sense than you’d think.
My partner used to laugh every time I’d see my parents print out their boarding passes three days before a flight. “You know it’s all on your phone, right?” she’d say.
Then we traveled through rural Thailand last year, and guess what? Not everywhere has reliable WiFi. Not every airline kiosk can pull up your digital confirmation. And when your phone dies at 3% because you’ve been using Google Maps all day, that printed paper suddenly looks pretty smart.
Boomers aren’t being old-fashioned here. They’re being practical. They remember what it’s like to travel without assuming technology will always work perfectly. And honestly? After being stuck at a check-in counter in Chiang Mai frantically searching for an outlet, I now keep a printed backup of major confirmations in my bag too.
It’s not about rejecting technology. It’s about having a Plan B when technology inevitably fails you.
I’ll admit it: when my grandmother mentioned she was using a travel agent to book her trip to Italy, I thought she’d lost touch with reality. This is 2025! We have Expedia, Booking.com, and seventeen other apps that do this for free!
But here’s what I didn’t understand: travel agents aren’t just people who book flights. They’re problem-solvers with actual relationships and leverage.
When my friend’s flight got canceled in Athens during a massive airline strike, she spent four hours on hold with customer service getting nowhere. Meanwhile, my grandmother’s travel agent had her rebooked on a different airline within twenty minutes. No hold music, no automated systems, just a human being who knew what strings to pull.
Travel agents also know things algorithms don’t. They can tell you which hotel rooms have the best views, which tour operators actually deliver, and which “deals” are actually terrible. That knowledge costs money, sure, but it’s often worth every penny when things go sideways.
Show up three hours before an international flight? That’s boomer paranoia, right? Millennials know you can breeze in ninety minutes before boarding and still have time for a coffee.
Except when you can’t.
I learned this the hard way flying out of LAX on a Friday afternoon. Construction had closed half the terminal. Security lines snaked back to the parking garage. I made my flight with about four minutes to spare, sweating and furious at myself for cutting it close.
Boomers aren’t showing up early because they’re anxious. They’re showing up early because they’ve lived through enough travel chaos to know that airports are unpredictable. Security lines surge. Terminals change. Shuttles run late. Traffic happens.
That extra hour isn’t wasted time. It’s insurance against the thousand small disasters that can derail a trip before it even starts. And honestly? Having time to sit down, breathe, and maybe grab a decent meal before a long flight isn’t the worst thing in the world.
My dad travels internationally with this elaborate system of envelopes containing different currencies, carefully organized and stashed in various pockets. I used to think this was absurd. Dude, credit cards work everywhere now. Venmo exists. Who needs physical money?
Then I spent a weekend in a small Portuguese village where exactly zero places took cards. Not the restaurant, not the little grocery store, not even the gas station. Cash only, and the nearest ATM was a forty-minute drive away.
Boomers remember that the digital payment infrastructure we take for granted isn’t universal. Rural areas, small businesses, developing countries, even some European spots that just prefer cash all operate outside our tap-to-pay bubble.
Plus, having local currency means you’re not getting destroyed by ATM fees and exchange rates every time you need money. That envelope system starts looking pretty smart when you’re not hemorrhaging 3% on every transaction.
Why would you eat the mediocre hotel breakfast buffet when you’re in Paris? Or Bangkok? Or literally anywhere with better food options within walking distance?
This was my attitude until I actually did the math on a two-week trip to Japan. Those “authentic local breakfast spots” were costing me $15-20 every morning. The hotel breakfast was included. Over two weeks, that’s $200+ saved, which paid for an entire extra day trip to Kyoto.
Boomers aren’t eating hotel breakfast because they lack culinary adventure. They’re eating it because they’ve learned that travel expenses add up fast, and free food is free food. You can still have your authentic local dinner and lunch experiences. But starting the day with included eggs and coffee? That’s just good budget management.
Plus, hotel breakfast means you’re fueled up and ready to go without having to research spots, wait for tables, or navigate unfamiliar neighborhoods before you’ve had caffeine. Sometimes efficiency beats authenticity.
I’ve mentioned this before but the shift away from Airbnb back toward hotels isn’t just a boomer thing anymore. But boomers never really left hotels in the first place, and it turns out they were onto something.
Hotels have staff. Twenty-four-hour front desks. People who can help when things go wrong. Cleaning services. Consistent standards. When I stayed at an Airbnb in Mexico City and the hot water stopped working, I spent three hours texting back and forth with a host who was “looking into it.” At a hotel, I would have called the front desk and had someone fixing it within thirty minutes.
Boomers value reliability over novelty. They want to know that if something breaks, there’s a system in place to fix it. They want someone to hold accountable if things go wrong. And after dealing with enough sketchy Airbnb situations myself, I completely understand why.
The “authentic local experience” of staying in someone’s apartment loses its appeal when you’re locked out at midnight because the keycode stopped working.
Nothing screams “tourist” quite like following a guide with an umbrella through a crowded square while they shout facts through a microphone, right? Real travelers explore independently, figure things out as they go, discover hidden gems.
But here’s what I learned exploring Venice on my own versus joining a walking tour in Prague: guides know things you will never find in any app or blog post. The Prague guide showed us a tiny courtyard that doesn’t appear on Google Maps, explained the symbolism in architecture I would have walked past, and connected historical dots I never would have made alone.
Organized tours aren’t about being lazy. They’re about learning from someone who actually knows what they’re talking about. Someone who lives there, who studied the history, who can answer your weird specific questions.
Sure, you can research everything yourself. But how many hours will you spend reading blog posts and watching YouTube videos to get maybe 60% of the context a good guide gives you in two hours?
My parents travel with luggage that could sustain them through an apocalypse. Extra shoes. Backup medications. A full first aid kit. Enough clothes for twice the trip length. Meanwhile, I’m over here with my carry-on and a dream, wearing the same three shirts in rotation.
This seemed ridiculous until I got food poisoning in Vietnam and desperately needed the anti-nausea medication I didn’t pack because “I probably won’t need it.” Or when it rained for four straight days in Seattle and I only had one pair of shoes, which were soaked and disgusting by day two.
Boomers overpack because they’ve learned that being prepared beats being fashionably minimalist when things go wrong. That extra pair of shoes isn’t wasted space when your only pair breaks. That backup medication isn’t unnecessary when you’re sick and can’t find a pharmacy that’s open.
There’s definitely a middle ground between my parents’ apocalypse preparation and my foolish optimism. But I’ve started leaning more toward their side of the spectrum, especially for longer trips.
Boomers love traveling in shoulder season. April instead of June. September instead of August. They’ll actively plan around avoiding crowds, even if it means potentially worse weather or shorter days.
I used to think this was just them being contrarian. But then I visited Rome in August, and it was legitimately miserable. Crowds everywhere. Forty-minute waits for everything. Prices inflated. Locals exhausted and less friendly.
The whole experience felt more like crowd management than actual travel.
The next year, I went back in October. Half the crowds, better prices, locals actually happy to chat, and the weather was still beautiful. The city felt completely different. More relaxed, more authentic, more like the place I’d imagined.
Boomers aren’t avoiding peak season because they’re weird about timing. They’re avoiding it because they’ve learned that popular doesn’t always mean better. Sometimes the best travel experiences happen when fewer people are having them.
Looking back at my parents’ Sedona trip, all those habits that seemed so outdated actually made perfect sense. They had backups for their backups. They knew exactly where they were going. They’d built in buffer time for things to go wrong.
Meanwhile, I was out here winging it with a phone battery and a prayer.
Boomer travel habits aren’t about being out of touch. They’re about having lived through enough trips to know what actually matters. Technology fails. Plans change. Things go wrong. And when they do, you’ll wish you had that printed confirmation, that extra cash, that travel agent’s phone number.
The best approach? Take the boomer wisdom on preparation and reliability, combine it with millennial flexibility and technology, and you’ve got something pretty solid.
Now if you’ll excuse me, I need to go print out my boarding pass for next month’s trip. Just in case.
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Jordan Cooper is a pop-culture writer and vegan-snack reviewer with roots in music blogging. Known for approachable, insightful prose, Jordan connects modern trends—from K-pop choreography to kombucha fermentation—with thoughtful food commentary. In his downtime, he enjoys photography, experimenting with fermentation recipes, and discovering new indie music playlists.
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