Travel has a funny way of teaching you things. The more you explore, the more your habits, opinions, and preferences evolve — sometimes dramatically. We sat down recently to think about what we actually do differently now compared to when we first started traveling together, and we came up with ten things that have genuinely shifted for us.
Fair warning: a couple of these might surprise you.
1. We Stopped Checking Bags (Most of the Time)
For most travelers, checking a bag is just… what you do. Especially for a longer trip. Three weeks in Europe? Of course you check a bag. But we’ve become true carry-on converts — and we’ve done trips as long as three weeks with just a carry-on and a backpack each.
The big driver here was switching away from budget airlines. With Spirit and Frontier (RIP Spirit — we still have feelings about this), it was actually cheaper to check a bag than to carry one on. But on airlines like Delta and American, where carry-ons are included and checked bags cost extra, the savings from skipping the checked bag add up fast.
And then there’s the time. After we accidentally gate-checked our bags on a flight to Mexico City and stood at the turnstile waiting… and waiting… it became very clear that never again was a reasonable policy. The freedom of walking off a plane and straight out of the airport is genuinely life-changing.
Could we do it in one bag between us? Absolutely not. But one carry-on and one backpack each? We’ve got a system. Maybe we’ll do a full packing episode one of these days.
2. We Arrive at the Airport Later Than We Used To
This one might actually shock some people, because the conventional wisdom is always get there early, get there early, get there early.
Here’s where we landed: since getting TSA PreCheck, security at most airports takes about ten minutes. So we’ve adjusted accordingly. For a typical domestic flight, we’re not showing up two and a half hours before departure anymore. For international flights or airports we’re less familiar with — sure, we build in more buffer. But the days of sitting at the gate for two hours eating an overpriced sandwich because we got there at the crack of dawn? Those are mostly behind us.
That said: we’re not thrill-seekers about it. We’re not the people showing up 40 minutes before departure and sprinting to the gate. We’ve just found a more reasonable middle ground.
3. We’ve Learned to Slow Down the Itinerary
This one’s hard to put into words, which is probably why it took us a while to articulate it.
The itineraries of our early travels were relentless. Hit everything. Check every box. See all the things. And honestly? We still do some of that — Mexico City was not a slow, meandering experience.
But somewhere along the way, especially on our longer trips, we’ve started to build in days that don’t have a plan. Days where the answer to “what are we doing today?” is genuinely “I don’t know, what do you feel like?” Days where you walk to the corner, get an espresso, sit in a window, and just look at a cathedral for a while.
It’s not about being lazy. It’s about making space for the kind of thinking and reflecting that travel uniquely enables. There’s something about being in a new place that opens up your mind differently — but only if you’re not constantly sprinting to the next attraction.
Southern Europe, with its built-in slow rhythm and siesta culture, has become very appealing for exactly this reason. There’s something to that way of living that we’ve started to seek out, even if it’s not naturally who we are at home.
4. Building in Quiet Moments
This is really the flip side of #3, and they go hand in hand.
It’s not just about doing fewer things — it’s about what fills those unscheduled pockets of time. Sitting in a café and watching the street. Noticing the birds. Lingering over a glass of wine with no particular need to be anywhere else. These moments used to feel like wasted time. Now they feel like the point.
Warm weather destinations actually help with this naturally. When the heat of the day rolls in, you have to slow down. Find some shade, get a cold drink, let the afternoon pass. We’ve come to appreciate that rhythm. There’s a reason the Mediterranean has been doing it this way for centuries.
5. We’ve Moved Away from Group Tours
We have our wonderful guide Laila in Mexico City to blame — or thank — for this one.
A private tour ruined group tours for us. Not because group tours are bad, but because the contrast was so stark. A private guide wants to know what you want to know. The experience bends around your interests and curiosity, not a fixed itinerary built for 30 strangers with 30 different priorities.
And we say this with kindness, because most people on group tours are perfectly lovely: there is always that one person. The one asking the guide a question they already know the answer to, just to demonstrate that they know it. You know the person. You’ve been on that tour.
That said, we haven’t written off tours entirely — not even close. We’ve come to deeply appreciate tours in the right context. Somewhere like the Anthropology Museum in Mexico City, a knowledgeable guide isn’t a luxury, it’s the difference between walking past artifacts and actually understanding what you’re looking at. And in places where there’s a language barrier, or deep cultural history you’d otherwise miss, a guide unlocks the whole experience.
We’ll keep taking tours. We’ll just try to make them private ones when we can.
6. We Book Third-Party Shore Excursions
Early in our cruising days, we fell for the cruise line line: book through us, or risk being left behind at port.
There is some truth to it — a third-party operator won’t hold the ship for you. But we’ve come to realize that the picture painted of stranded passengers is fairly overblown. These operators run their businesses on reputation and referrals. Getting people stuck at port is not a sustainable business model. Many of them also offer to arrange transportation to the next port if something goes wrong.
More importantly, we’ve seen what cruise line excursions actually look like in practice. On one port day, the ship’s big bus tour had us back at the dock with six hours still to go before departure. Six hours sitting at the port, not exploring. Meanwhile, the private small-group tour we took in the Azores took us up viewpoints the cruise buses literally couldn’t reach. We looked down from the top of a hill and there was the big tour bus, stuck far below.
The Azores experience cemented it: small group, a knowledgeable guide, flexibility to go where the big operators can’t. That’s the experience we want.
7. We’ve Cooled on Cruising in Europe
We are still cruisers. There’s a cruise coming up very soon on our end, and we continue to seek out great sailings. But we’ve genuinely changed our minds about where cruising makes sense for us.
The Mediterranean? We’re not sure it’s the right way to experience Europe anymore. Over-tourism is a real and serious problem in those ports, and the places cruise ships dock are often the exact places already overwhelmed with crowds. You get a few hours in a port city, you see the surface, and then you’re herded back to the ship.
The Caribbean, on the other hand? We think cruising is genuinely ideal there. Many of those islands are difficult to reach otherwise — you’d be booking multiple small flights or chartering a boat. The cruise becomes the practical, affordable, fun way to island-hop.
So it’s not that we’ve quit cruising. It’s that we’ve gotten more intentional about where it makes sense.
8. We Think Less About Public Transit
Look, Ashleigh is just going to come out and say it: she doesn’t love crowded public transit. There. It’s out there.
The Chicago blue line incident — packed to the gills, someone’s backpack inches from her face — cemented something that was already quietly true. Given a choice between a crowded train and walking a mile and a half, she is walking. Every time.
Now, this isn’t a blanket anti-public-transit stance. The RER from Charles de Gaulle into Paris was perfectly fine. There are times when it’s clearly the right call. But when planning a trip now, we think first about whether we can walk somewhere, and then about other options. Public transit is still on the table — it’s just not the automatic first answer it might have been before.
9. We’ve Cooled on Disney (A Little)
This one’s a long time coming, and if you followed the Generation Mouse podcast, you probably saw it on the horizon.
We’re not done with Disney. We’d go to Disneyland again. We still plan to be in the parks for Epcot’s 50th anniversary. But the urgency we once felt about Disney World specifically — that has faded. After our 2024 trip, we felt genuinely satisfied. Good for a while. And as the years have gone by and we’ve continued to explore the world, Disney has drifted lower on the priority list.
It’s not a complaint. It’s just that the world is very large and very interesting, and there are only so many weeks in a year.
10. We Actually Enjoy the Beach Now
File this one under “things we didn’t see coming.”
For years, the beach was tolerable at best. Hot. Sandy. Uncomfortable. Not particularly interesting for someone who doesn’t default to relaxing. And beach vacations in our childhood didn’t exactly involve umbrellas or chairs — just a towel in the direct sun and an expectation of enjoyment.
But something has shifted. Recent trips to Puerto Rico, with a swim in the morning, a wander through the kiosks, some great food, and heading in before the heat of the day — that version of the beach works. Getting there early before the crowds arrive, getting in the water, drying off, and leaving before things get miserable? That’s a day at the beach we can get behind.
We still stand by our assessment that when you go somewhere like Puerto Rico, you should absolutely do more than just go to the beach. You’d be missing so much. But the beach itself? It’s earned a spot on the itinerary now.
What’s Changed for You?
Travel is one long education. Every trip teaches you something — about the places you visit, sure, but also about what you actually want from the experience.
Thanks for stopping by! Check out our Go See Do Explore Podcast, available wherever you listen to podcasts. To read about some of our previous trips, visit my Trips Page. If you like my photos be sure to “like” my Facebook Page and follow me on Instagram! For my list of gadgets to make your travels easier, click here.
Leave a Reply