7 millennial travel habits that would confuse every boomer dad

My dad called me last week, genuinely concerned. "You're staying in someone's apartment? A stranger's apartment? And you found this on the internet?"

He was talking about my Airbnb in Lisbon. I tried explaining that millions of people do this every day, that there are reviews and verification systems, that it's perfectly safe. He wasn't convinced. "In my day," he said, "we stayed in hotels. You knew what you were getting."

That conversation got me thinking about how differently my generation approaches travel compared to our parents. It's not just about technology. It's about values, priorities, and what we consider worth spending money on.

Here are seven travel habits that would absolutely baffle every boomer dad out there.

1. We book accommodations through apps we've never used before

My father has stayed at the same Holiday Inn chain for thirty years. He knows what to expect: continental breakfast, ice machine down the hall, HBO in the room.

Meanwhile, I'm scrolling through Airbnb at midnight, booking a converted shipping container in Joshua Tree or a treehouse in Costa Rica. The reviews look good, the photos seem legit, and honestly? That's enough.

Boomers built trust through institutions and brand names. We build it through crowd-sourced reviews and social proof. Neither approach is wrong, but they're fundamentally different ways of assessing risk.

When I showed my dad the place I stayed in Porto last year (a local artist's spare room with a balcony overlooking the Douro), he just shook his head. "But what if it was terrible?" What if it was amazing, I thought. And it was.

2. We don't actually plan that much

My parents' vacations came with three-ring binders. Printed confirmations, highlighted maps, restaurant reservations made six months in advance. Everything scheduled down to the hour.

I landed in Bangkok once with a hostel booked for two nights and absolutely nothing else planned. My mom nearly had a heart attack when I told her.

Here's the thing though: having a loose itinerary isn't about being irresponsible. It's about staying flexible enough to follow opportunities when they appear. That unplanned approach led me to a cooking class recommended by someone I met at a coffee shop, which led to a friendship that's lasted five years.

Does this occasionally backfire? Absolutely. I've definitely scrambled to find accommodation at the last minute or missed out on popular attractions because I didn't book ahead. But for me, the spontaneity is worth the occasional hassle.

3. We work while we travel

"Isn't the point of vacation to NOT work?" my dad asked when he saw me answering emails from a beach in Mexico.

In his world, vacation meant two weeks off per year, completely disconnected from the office. You went somewhere, you relaxed, you came back.

But the laptop lifestyle has changed everything. I've written articles from cafes in Prague, edited photos in Bali, taken calls from Airbnbs in Montreal. I'm not working the whole time, but I'm also not completely offline.

This isn't about being a workaholic. It's about the fact that remote work has made extended travel possible in ways it never was for previous generations. My dad had to choose between his career and long trips abroad. I can do both simultaneously.

The trade-off is real though. There's something to be said for true disconnection, for being completely present in a place without the pull of deadlines and Slack notifications. I've mentioned this before but finding that balance between productivity and presence is an ongoing challenge.

Some of my boomer relatives think this defeats the purpose of travel. I think it makes travel accessible in ways it wasn't before. Neither of us is wrong.

4. We eat street food and think it's a highlight

My father will not eat food from a cart. Period. "You don't know how long it's been sitting there," he says. "You don't know if it's safe."

Meanwhile, some of my best travel memories involve sticky fingers and paper plates. Tacos from a vendor in Mexico City. Pad thai from a stall in Chiang Mai. Arepas from a street corner in Bogotá.

This isn't just about being adventurous. It's about recognizing that street food is often where you find the most authentic local flavors, prepared by people who've been perfecting their craft for decades.

Obviously, you need to use common judgment. I'm not eating raw seafood from a questionable source in ninety-degree heat. But dismissing all street food means missing out on extraordinary experiences.

Plus, let's be honest: that michelin-starred meal in Paris was incredible, but I think about those dumplings I ate from a folding table in Taipei way more often.

5. We optimize for Instagram moments

"Why do you need fifty pictures of the same thing?" my dad asked while watching me photograph my acai bowl in Rio from seven different angles.

Fair question. But here's what he's missing: documenting travel isn't just about memory keeping anymore. It's about storytelling, sharing experiences, and yes, sometimes building a personal brand.

I spent an entire afternoon last year finding the perfect angle of Lisbon's pink street (you know the one) because I knew that photo would resonate with people. Was it authentic? Kind of. Was it performative? Also kind of. Does the distinction matter as much as we think it does?

The criticism that millennials experience places through screens is partially valid. I've definitely watched sunsets through my phone and later regretted it. But I've also built connections with people across the world through shared travel content.

My photography background has taught me that documentation and experience aren't mutually exclusive. You can be present AND capture the moment. The key is knowing when to put the camera down.

Boomers preserved memories through photo albums no one ever looked at. We preserve them through digital galleries we actually revisit and share. Different methods, similar intentions.

6. We choose experiences over stuff

When my parents traveled, they brought back souvenirs. Fridge magnets, shot glasses, decorative plates. Physical proof they'd been somewhere.

I came back from three weeks in Southeast Asia with photos, journal entries, and zero physical objects beyond the clothes I wore.

This shift reflects a broader millennial value system that prioritizes experiences over possessions. We'd rather spend money on a cooking class, a hiking tour, or a concert than on things we'll shove in a drawer.

My dad doesn't quite get it. "But what do you have to show for it?" he asks. Everything, I think. Just nothing you can hold.

There's also a practical element. I've moved six times in ten years. Accumulating stuff just makes that harder. Collecting experiences instead of trinkets makes perfect sense when your life is more mobile.

7. We travel to work on ourselves

This one really confuses boomer dads.

"You're going to India to 'find yourself'?" my father asked, making air quotes with genuine bewilderment. "You know where you are. You're right here."

But travel as self-discovery isn't about being lost. It's about stepping outside familiar contexts to gain perspective on who you are and what you want.

I've spent time in hostels having deep conversations with strangers about purpose and meaning. I've taken solo trips specifically to sit with uncomfortable feelings and figure things out. I've used travel as a laboratory for testing different versions of myself.

My parents' generation traveled to relax and see sights. We travel to transform. It sounds pretentious when I write it out like that, but it's true.

Does every trip need to be a spiritual journey? Of course not. Sometimes you just want to drink wine in Tuscany and that's perfectly fine.

But the option to use travel as a tool for personal growth feels valuable in ways previous generations didn't necessarily prioritize.

Conclusion

My dad will probably never understand why I slept in a hostel dorm room at thirty-five or why I spent an afternoon photographing tiles in Porto instead of visiting the museum.

That's okay. His generation had their relationship with travel, and it worked for them. Hotels with rewards programs, guided tours, advance planning, disconnection from work, and clear itineraries gave them what they needed.

Our approach reflects different priorities, different technologies, and different economic realities. We're not more enlightened, just adapted to a different landscape.

The next time your boomer dad questions your travel choices, remember: you're not doing it wrong. You're just doing it differently. And honestly? That's what makes both generations' stories worth sharing.

Now if you'll excuse me, I need to book a last-minute flight to somewhere I've never been. My dad would be horrified. I can't wait.