[ DISCOVERY · THE DISPATCH ]

I Stopped Planning My Trips and My Vacations Got 10x Better

I used to build color-coded spreadsheets for every trip. Then I blew one up mid-vacation — and accidentally had the best week of my travel life.

I used to be the person who sent the group chat a color-coded Google Sheet two months before departure. Fifteen-minute transit windows. Restaurant reservations at places I’d bookmarked based on a YouTube video I watched in January. A backup café for every backup café.

And I was miserable on vacation.

Not the whole time — the planning part was genuinely fun, in the way that solving a puzzle is fun. But the actual trip? I spent it staring at my phone, anxious that we were running six minutes behind, annoyed when someone wanted to browse a market stall we hadn’t scheduled.

The thing that broke me was a Tuesday in Porto.

We’d blocked out exactly 47 minutes for the Livraria Lello bookshop (it was in the spreadsheet, color-coded orange for “culture”). We got there, saw a line stretching around the block — about 90 minutes of wait — and my first instinct was to skip it and protect the schedule.

My travel companion, a far saner person than me, said: “Or we just wait.”

We waited. We got talking to a retired schoolteacher from Galicia who’d been to Porto eleven times. He told us about a tiny tasca around the corner from our hotel — no sign, open only for lunch, cash only, bacalhau com natas that had made him cry — that had zero Google reviews because the owner didn’t believe in the internet.

We went. It cost about 9 euros a person. It was, without exaggeration, the best meal of the trip. The meal was not in the spreadsheet.

The problem with a dense itinerary isn’t that it’s ambitious. It’s that it treats travel like a project with deliverables. You’ve pre-decided what the best version of the trip looks like — and then you spend the whole time defending that version against reality.

Reality always has better ideas.

When you’re locked into a schedule, you can’t follow the interesting stranger. You can’t spend three hours in a garden because the light is doing something extraordinary. You can’t say yes to the invitation you didn’t expect.

There’s a concept I’ve seen come up again and again when I talk to long-term travelers — and something I touched on in my piece about the hidden tensions in cities marketed to remote workers — which is that the best destinations reward the people who aren’t rushing through a checklist. They reveal themselves slowly, to people with slack in their days.

That’s not a poetic abstraction. It’s a practical truth. The good stuff is off-schedule.

Here’s where I want to push back on the purity version of this advice, because “just be spontaneous, babe” is genuinely bad guidance for most travelers.

Zero structure creates its own misery. I’ve done that trip too — landed somewhere without even a hotel booked, and spent the first three hours of vacation hauling a heavy bag around trying to find a room that wasn’t either a party hostel or a mold situation. That’s not freedom. That’s friction that eats your energy before the trip even starts.

What I actually practice — and what made Portugal and every trip since dramatically better — is what I call structured spontaneity. It’s a small framework:

Lock the logistics. Leave everything else open.

Specifically:

• Flights booked (obviously)
• First and last night’s accommodation confirmed — you need to land somewhere and know where you’re sleeping before the jet lag hits
• One “anchor” activity per day maximum — something you genuinely care about, booked in advance if it requires it
• Everything else: decided the night before, or the morning of, based on how you feel and what you’ve discovered

That’s it. No restaurant list. No must-see checklist. One anchor, real logistics, and space.

Before I leave, I spend maybe two hours on research — not to build an itinerary, but to build a list of possibles. Restaurants that look good. A neighborhood I’m curious about. A day trip that might be worth it. A museum that might be worth skipping.

This list lives in my Notes app, unordered, unkept. It’s not a schedule. It’s a menu.

Each evening — usually over dinner or a beer — I pick one thing from the menu for the next day and confirm any booking it needs. Then I go to sleep. That’s the whole planning session. About 10 minutes.

The rest of the day flows from what the morning looks like, who I’ve met, what the weather is doing, how my feet feel. On the Porto trip, I ended up spending half a day in a neighborhood I’d never heard of because someone at a café told me to go there. No regrets.

For anyone who travels internationally and wants to keep the admin low, I’ve also started traveling with an eSIM setup that keeps connectivity cheap without hunting for SIM cards in every country — I wrote about the specific eSIM stack that runs me about $8 a month across 40 countries if you want the details.

Here’s the thing the “just go, figure it out” crowd won’t tell you: local context still matters.

Not in the form of a schedule. But in the form of knowing the basics: when things are actually open (a lot of Europe closes midday, closes Sundays, has random public holidays you need to check for), which neighborhoods require more planning to access, and what local custom might make you accidentally rude.

You don’t need a spreadsheet for this. You need 45 minutes of reading before you leave.

I also keep a note of what’s definitively not worth doing at each destination — the tourist traps, the overrated landmarks, the things that have 50,000 reviews and three stars because every reviewer was also disappointed. Knowing what to skip is as valuable as knowing what to find.

The hardest part of this approach is doing it with other people, especially people with different travel personalities. One person’s “liberating flexibility” is another person’s “we’ve been standing on this corner for twenty minutes and I’m hungry and why didn’t we just have a plan.”

A few things that actually help:

• Align on the framework before you leave, not when you land. If your travel partner needs more structure to feel comfortable, add one more anchor point per day. Negotiate on the front end.
• Use the veto, freely. Either person can veto a spontaneous suggestion without explanation, and it gets dropped without drama. This makes saying yes feel safer.
• Designate a “decider” for each half-day, rotating. Eliminates the “I don’t know, what do you want to do” loop that eats 40 minutes outside every café.

If you want ideas for destinations that reward this kind of open-ended exploration, the full itineraries library has suggestions by region — useful for finding your anchor activity and then leaving the rest loose.

I’ve been traveling seriously for about nine years. The trips I remember — the ones I’d repeat tomorrow if I could — are never the ones where I executed a perfect schedule. They’re the ones where something unexpected happened and I had enough slack to follow it.

The bacalhau in Porto. A three-hour conversation in a Buenos Aires bookshop that turned into a wine-soaked dinner with strangers. Getting intentionally lost in the medina in Fes and finding a courtyard that felt like it was from a different century. A spontaneous detour to a vortex site in Sedona on a roadtrip that I’d written off as “too woo-woo” until someone talked me into it.

None of those were in a spreadsheet. All of them required me to have time.

The best version of your next trip is probably not in your itinerary — its in the margin around it.

Give the margin. That’s where the trip actually happens.

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