034 Optimizing Travel
The Best Moment of Our Wildest Italy Trip Was Doing Absolutely Nothing
There's a window in Bologna, Italy, I still think about.
We were in the middle of our second trip through Italy — the one that went completely sideways. Missed trains. A ticket booked for the wrong day. Rain so heavy we were soaking wet just trying to walk to the next museum. Ashley sick before the flight home. Everything that could go wrong, did.
But that hotel room in Bologna, where we did almost nothing for two days? That's what I remember most.
The cathedral choir drifting through the open window. Lunch in the square with nowhere to be. Not unpacking the suitcase because we didn't have to. It sounds crazy — you are in Italy, you paid to get there, you should be seeing things — but that's the moment that stuck.
Ashley and I talk about travel constantly. It's probably the question we get asked most. And the more we unpack our best trips and our worst ones, the more we realize it all comes down to one thing: the difference between executing a plan and actually having an experience.
Travel Starts With a Decision Most People Skip
Before you book anything, before you look at flights or hotels, there's a question worth sitting with: what is the purpose of this trip?
It sounds obvious. But most people skip it and go straight to logistics.
If work has been relentless and your tank is empty, you need a trip built around doing nothing — a cabin in the woods, a beach where the hotel is so nice you don't want to leave the property, a porch and a view and zero agenda. That's a different trip than Rome or London or any city where you're going to walk fifteen miles a day through history.
Ashley and I have learned to alternate. One year we go full intensity — big city, long days, packed itinerary. The next we pull it back. Beach. Mountains. Somewhere you go to be, not to do. It keeps both of us fed. Because we genuinely love both, and burning out on one style makes you resent the whole idea of travel.
The other decision couples rarely make explicit: who owns what. Ashley is the planner. She's researched every hotel, read every review, knows the transit pass that covers the whole city. I'm the one who figures out how to actually get there once we arrive — the navigation, the logistics on the ground, the pivot when the plan goes sideways. We used to have that imbalanced, everything loaded onto her. Now we play to our strengths, and the whole thing breathes easier.
The Money Lie People Tell Themselves
Growing up, we didn't take vacations. I know a lot of people who didn't.
And somewhere in that upbringing, a story gets written: travel is for other people. For people with more money. For some future version of your life that never quite arrives.
Our first real trip was Colorado. We saved our tax return, our Christmas money, a little every month for a year. Ashley rented a cabin, we bought groceries, cooked most of our own meals, planned two nice dinners out. I called myself conservative back then. Honestly, I was just cheap. There was real guilt around spending money we could have put somewhere else.
And then it snowed two feet while we were there. We were snowed in for days — hot tub, mountains, nowhere to go. That trip is still one of our most vivid memories. Not because of what we spent. Because of what we did.
Ashley said something that reframed it for me: she couldn't tell you what we bought each other for Christmas twelve years ago. But she can describe that blizzard, the train up Pike's Peak, meeting friends in Colorado along the way - like it was last week. That's the investment. Experiences compound in a way stuff never does — and Glenn Lundy's framework from Episode 19 on investing versus spending applies here as much as anywhere.
That Colorado framework unlocked Italy. My brother was stationed there with the Air Force for eight years. We kept saying we'd go, kept not being serious about it, and then finally he said: you've got one year left. We said fine. We used the same approach — save for the year, keep expenses lean. Staying with him meant accommodations were mostly covered. Flights and food. We could wrap our heads around that. And that trip is what caught the travel bug for us permanently.
You don't have to start with Bora Bora. A weekend two hours away, a cabin in Northwest Arkansas, a few days at Branson — that counts. Building the habit, the rhythm, the practice of saving for it and then actually doing it? That's how you get to the big trips eventually. Same as any other compounding habit we talk about on this show.
The Over-Planning Trap (Ashley's Confession)
Here's something Ashley will be the first to admit: she over-researches.
Every YouTube video. Every blog. Every travel forum thread. By the time we arrive somewhere, she has so much information she doesn't know how to give it to me, doesn't know what's actually relevant, and can't stop trying to manage it all.
The problem with that — and she saw a reel recently that nailed it — is that it turns an experience into execution. You stop arriving somewhere with wonder. You arrive with a checklist. And when the checklist breaks down, the anxiety compounds because you've built this thing in your mind for months and now it's not matching.
It's like reading the book before watching the movie. When has that ever not led to disappointment
The chaotic Italy trip was the sharpest lesson. Missed trains. Wrong day on a booked ticket. Rain. Everything cascading. But what Ashley said afterward stuck with me: had we not been doing the mindset work we'd been doing, had we not been building the habit of gratitude and learning to communicate under pressure the way we'd been learning to do in our marriage, that trip would have broken us. Instead, at one point we were walking through Rome absolutely soaked, and we just started laughing. You find the joy or you lose the trip.
Old Ashley, she said, would have responded to all of that very differently.
The Alaska Revelation and the Art of Buffer Days
After the chaotic Italy trip, we did an Alaskan cruise. And something shifted.
We'd always been skeptical of cruises. You're stuck on the boat. You only go where they port. Why wouldn't you just go wherever you want?
But after ten days of living out of a suitcase, city to city, never fully unpacking — the cruise was like a different planet. You unpack once. The ship takes you somewhere. You get off if you want. You don't if you don't. You go to the comedy show at night and your bed is a ninety-second walk away. There's no parking, no driving home at 2am, no figuring out the metro. I finally understood why people do it.
The bigger lesson there — and it applies whether you're on a cruise or in a foreign city — is buffer days. Protect them like appointments. Ashley started building in at least one full day in the middle of any big trip that has nothing mandatory on it. Sleep in. Sit in a café. Walk without a destination. It sounds like wasted time and it is the furthest thing from wasted time.
The guilt is real. You paid to be here. You should be maximizing. But maximizing is what turns a trip into work. The Bologna days where we did nothing are the ones I remember. The best memories from the craziest trip we ever took — and they were the days with nothing on the itinerary.
How AI Changed the Way We Plan
One more thing worth naming: AI has become a legitimate travel tool, and not just for itinerary building.
The old way was watching thirty YouTube videos and reading a dozen blogs and arriving somewhere completely over-informed. Ashley would know too much, couldn't filter it, couldn't translate it to me in real time.
The better way — and we talked about this extensively in Episode 33 — is to use AI to curate the information rather than consume everything available. Ask it the top five things to know about a neighborhood. Ask it which transit pass makes sense for your specific dates. Keep it surface-level until you need depth. You stay in the driver's seat of what you learn, which means you can still arrive somewhere with a little bit of wonder intact.
That's not over-optimization. That's the right kind of prep.
The Question Worth Asking Yourself
What's on your list?
Not the theoretical list. The one you actually think about. The place that keeps coming back up when someone asks where you'd go if money weren't the thing stopping you.
Here's what Ashley said about Italy: that was the trip that proved to her it was possible. Before that, it was an idea. After it, it was a category of life they'd figured out how to invest in.
Start there. Not with the perfect itinerary or the biggest trip. Start with the savings habit, the small trip, the weekend away that builds the muscle. Because experience is the asset that actually appreciates — and you don't have to wait until everything lines up perfectly to start collecting it.
Growth happens when you take action. Daily anything changes everything.
Resources
Related Episodes
Episode 33 — Optimizing with AI: A Thought Partner — We go deep on how to use AI as a curated research tool, not just a search engine. Directly relevant to the travel planning conversation. → Watch on YouTube
Episode 28 — Over-Optimization — The tension between planning and living shows up in more places than travel. → Watch on YouTube
Episode 19 — The Power of Morning Routines ft. Glenn Lundy — Glenn's invest vs. spend framework applies directly to how you think about budgeting for experiences. → Watch on YouTube
Episode 30 — 17 Years, A Look Back ft. Ashley Negron — More on how travel and shared experiences have shaped our marriage over time. → Watch on YouTube
Products We Use for Travel
💧 LMNT Electrolyte Drink — staying hydrated while traveling, especially on long flights and active days (referral link)
📖 Kindle — the best thing we ever added to carry-on travel (affiliate link)
Listen to the Full Episode
This post is drawn from Episode 34 of the Optimizing Beyond Podcast: Optimizing Your Travel ft. Ashley Negron.
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