My wife and I had just arrived in Amsterdam, the first stop on our three-week European trip with about 10 destinations.
As we stepped off the train, we prepared to bask in the “we made it halfway across the world from Reno” feeling as we embarked on a peaceful canalside walk to our hotel.
Instead, we walked straight into SAIL Amsterdam 2025 alongside about 2 million of our closest friends. We had no idea the massive festival was happening.
Navigating all the crowds would’ve been fine … if we hadn’t packed as though Europe might run out of clothes.
I’m a contingency planner by profession, which made things worse. I’d packed two sport coats, four pairs of shoes, two neckties, a London Fog overcoat, and my masterpiece: a clothing steamer. I used the steamer exactly zero times on the whole trip.
Meanwhile, my backpack contained basically my entire work life: two laptops, an iPad Pro, chargers, adapters, and enough cords to wire a small data center. I also brought a “mini studio” for recording keynotes — a tiny tripod, portable mics, and a headset — plus a camera bag with more lenses than any normal person needs.
My wife and I managed to hit 49.9 pounds (just under the 50-pound limit) on both checked bags, which felt like we were winning at travel. Then we tried carrying them — plus two overloaded carry-ons each — and instantly proved ourselves wrong.
The stupid part is that we’ve been to Europe before, and we do know how to travel. Before leaving, we even swore we’d try seasoned travel writer Rick Steves’ method of packing minimally and fitting everything in just one carry-on bag each.
Then we ignored basically every sentence Rick has ever written.
Overpacking weighed us down for the entire trip
The walk from Amsterdam Centraal to our hotel was supposedly short. In practice, it felt never-ending as my suitcase wheels hit cobblestone and immediately staged a protest.
The wheels locked up, and I dragged it along while locals and tourists alike walked by with light backpacks and the calm expression people get when they’re watching someone lose an argument with a screaming toddler. To be fair, I felt like I was.
And that became the pattern across city after city. Brussels. Bruges. Ghent. Avignon. Same scene: me hauling a stubborn suitcase over ancient stones and swearing under my breath.
Our itinerary also included Porto, the Douro Valley, Toledo, Sevilla, Madrid, and Segovia. On paper, seeing all these places was awesome.
In reality, packing, moving, and then unpacking so much stuff felt as if we were being evicted every 72 hours.
Porto is where the trip finally put me in my place. Between the hills and the luggage, I started cursing everything, especially stairs and cobblestones.
I set an alarm for sunrise photos, but by then I was so exhausted from lugging my bags around that I slept through it. By Toledo (and then Segovia), we weren’t “traveling Europe.” We were commuting through it with enough luggage to make me question my life choices.
And then I noticed them: the Rick Steves type of travelers. Calm. Unbothered. Guidebook open. Backpack on the back, smaller one on the front, hands free, and walking like this was normal.
And the worst part? Those backpacks looked like the ones so many lists and guides recommend. The same kind I bought before we left … and returned, because I looked at them and thought, “Nope, these are too small.” I couldn’t bear not being able to bring all my “what if” clothes.
Meanwhile, my wife and I looked like the American tourists we swore we wouldn’t be — overloaded, swapping hands, rearranging straps, and acting like travel is something you just power through.
I wanted to blend in. I wanted to look effortless, like the guy who “just wanders.” But nothing blows your cover faster than dragging a 49.9-pound suitcase over centuries-old cobblestones while carrying a camera bag and a strong case of self-doubt.
After that trip, we plan to never travel or pack this way again
I don’t regret lugging around my camera because the photos do matter. The rest? Never again.
Don’t get me wrong: we enjoyed the trip. We ate well, saw beautiful places, and made memories we’ll talk about forever. It just could’ve been a whole lot more relaxing if we weren’t constantly managing our stuff — and our packed schedule — like it was a small business.
Next time, I’m limiting myself to one bag I can lift without giving myself a pre-game pep talk. No specialty gear I don’t use at home, and absolutely zero appliances that produce steam. We’re also focusing on fewer destinations and longer stays.
And as for the Rick Steves travelers? I plan to join them — lighter, calmer, and finally traveling like I’ve done this before.
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