People assume planning a big international trip swallows weeks. It doesn’t. What swallows weeks is researching — the open-ended, tab-hoarding, “let me just read one more list” spiral that feels like progress and isn’t.
I am not an over-planner. I’m also, very much, not an under-planner. I land somewhere in the middle that I’ve gotten faster at over the years, and the speed didn’t come from caring less. It came from knowing what to decide first and what to leave alone.
Here’s the system I actually use.
The real reason trip planning takes forever
When I started traveling internationally about ten years ago, my problem was never too little information. It was too much. There was an ocean of it, and no good way to tell the high-quality sources from the noise. So I’d read, and read, and feel less decided with every hour.
What changed wasn’t the internet. It was me. The more I traveled, the more I learned what I actually like — and “what I like” turns out to be the fastest filter there is. Once you know you’re a walking-tour person and not a hop-on-hop-off-bus person, ninety percent of the internet stops being relevant to you, which is a wonderful thing.
So this isn’t really a post about planning faster. It’s about deciding faster, and letting the planning fall out of the decisions.
Start with the two or three things you actually care about
This is my single biggest recommendation, and it’s the one most people do last instead of first.
Before dates, before flights, before anything: figure out the two or three things you genuinely care about doing on this trip. For a seven-to-ten-day trip, that’s usually three big things for me, plus a handful of smaller ones that mesh well with the rest. Everything else gets planned around those anchors.
My rule for the anchors is simple: do the thing you do in that place. I eat the local specialty — if there’s a delicacy, I’m trying it; I’m not saying no to anything local. I take the walking tour and learn the culture. I’d rather learn to make perfume in Paris or sit with a Buddhist monk in Thailand than buy a fridge magnet. I want to sit in a coffee shop in a regular residential neighborhood and absorb what it’s like to live there. I know the version I get as a tourist is a curated, beautifully painted slice, not the whole society. But even the curated slice, I love.
What I don’t do: the cheesy stuff. I’m not interested in anything you could do on a short stop off a cruise ship, and I’m not browsing a souvenir shop. That’s not snobbery. It’s a filter — and the filter is what saves the time.
Then I protect the rhythm. I schedule a maximum of one real thing per day, ideally a half-day activity, so the rest of the day stays loose and I can adjust, rest, or follow a recommendation a local just handed me. On a longer trip I’ll leave a couple of days with nothing scheduled but something possible — cushion days. They are not wasted days. They’re the days the trip actually breathes.
Pick your dates by the season, not just the calendar
Once I know the anchors, I know roughly how long the trip needs to be. Then I find the dates: I look at where I have a gap in my schedule, and — this is the part people skip — I check what the best places to visit during that window actually are.
A recent example: I wanted to go somewhere in Asia, looked at my window, and learned it was going to be brutally hot almost everywhere I was considering. So I didn’t go to Asia then. That’s not a failed plan; that’s a five-minute check saving a sweaty, miserable trip.
I’m also a big believer in shoulder and off-season travel. I love Park City in the summer, when it’s a ski town with no skiing and all the trails. Same with Breckenridge. You wake up somewhere beautiful, do the thing, and often stay in a high-end hotel at a deeply discounted price simply because you were willing to go when the crowds weren’t. Off-season isn’t a compromise. A lot of the time it’s the upgrade.
Book in the right order so you never redo work
Order matters, because the wrong order means re-doing decisions. Mine goes:
- Lock the anchors first — the top-priority activities I came for.
- Then figure out where to stay. I triangulate lodging from the activities: where’s central to the things I’m doing?
- Default to central over luxurious. A tiny room in the middle of everything beats a gorgeous suite a forty-minute trek away, every time. The whole point is to be close to what you came for.
- Minimize hotel moves. Changing hotels mid-trip means the awkward limbo where you’ve checked out of one place and can’t yet check into the next, hauling your luggage around a city. I avoid it when I can — but I won’t waste hours backtracking to the same hotel if moving once genuinely makes the trip better.
One caveat that rewrites this whole section: if I’m flying standby, I don’t book accommodations until the plane’s wheels are up. (More on that in Flight Benefits Explained.) When the flight itself is a maybe, you keep everything else a maybe too.
The booking order that saves you the most time
Order matters — the wrong one means redoing decisions. Work top-down:
- Lock your anchors first — the 2–3 experiences you actually came for.
- Book lodging around those anchors — central to what you’re doing beats a nicer room that’s a 40-minute trek away.
- Slot flights and transport once your dates and home base are set.
- Minimize hotel moves — switching mid-trip costs you a half-day of luggage limbo.
- Leave restaurants and day trips for last — they’re easy to fill in once the skeleton holds.
The spreadsheet that runs the trip
My planning lives in one Google Sheet, and it has outlasted every app I’ve tried.
Every date goes in, labeled by day of the trip. Under each day: where I’m staying, my confirmation details, the neighborhoods I want to explore, and — planned around the day’s activity — the neighborhoods I want to eat in. It’s not fancy. It’s just everything in one place that I can actually keep.
The unexpected proof that it works: people I’ve traveled with have, more than once, recommended my spreadsheet to their friends and then come back to ask me for a copy to pass along. (The itinerary, obviously — not my confirmation numbers.) When the thing you built to organize your own trip starts getting forwarded around like a chain letter, you’ve probably got a decent system.
Use AI as a filter, not a firehose
This is the part that genuinely collapsed my planning time. I use Claude or ChatGPT the way you’d use a high-touch travel agent — to do the legwork. Itineraries, recommendations, narrowing a hundred options down to a handful, the grunt research that used to eat my evenings.
And I do it by the numbers. I ask things like “what are the highest-reviewed walking tours in this city,” or about UNESCO World Heritage sites, or the highest-rated market tours. I trust the masses for a general read, then pare it down to what I personally know I like — walking tours, market tours, a local class — and cut what I know I don’t. The crowd tells you what’s good; you tell you what’s good for you. The combination is faster and better than either alone.
Two prompts that collapse the research
Use Claude or ChatGPT like a high-touch travel agent — to do the legwork, not make the decisions. Copy these to start:
- “Act as a detail-oriented travel agent. I’m going to [place] for [X days] in [month], and I care most about [your 2–3 priorities]. Build a day-by-day skeleton that keeps travel time low and groups things by neighborhood.”
- “Here are [paste your options]. Narrow them to the 3 best for [priorities + budget], and give me the one real downside of each.”
How far ahead you actually need to start
My rule of thumb: an international trip only needs to be booked as far ahead as it takes your entry paperwork to clear.
For most places a U.S. passport goes, that’s no time at all — so book it whenever. Last-minute might cost you, or it might be a steal, but the months-of-runway thing is mostly a myth. I’ve practically booked from the gate.
But — and 2023 me learned this at a boarding gate in a cold sweat — do check the entry paperwork before you go, because the quick “it’s not a visa, but…” authorizations keep multiplying. As I write this in 2026: the U.K. now requires an ETA for U.S. travelers (enforced since February), the E.U.’s ETIAS is expected to launch later this year, and South Korea has U.S. travelers complete a free e-Arrival Card before boarding (its K-ETA is waived for us through the end of 2026). None of them take long. The ones that are live can stop you at the gate if you skipped them — so check what your destination wants the year you go, because this list only gets longer.
The part where you just book it
The fear isn’t really that you’ll plan badly. It’s that you haven’t planned enough — that there’s one more list, one more thread, one more perfect thing you’ll miss if you stop researching now.
You won’t. Enough research beats all the research, because all the research doesn’t exist; there’s always more, and the trip you keep researching is the trip you never take. Pick your two or three things. Size the trip around them. Book the anchors, stay central, leave room to wander. Then close the tabs and book it.
The plan was never the hard part. Deciding was. And you just did.
More life. Anyway.
Want the shortcut? Grab the free First Solo Trip Playbook and plan your next trip without the overwhelm — the step-by-step companion to this system.
Related: you don’t need a different life to start living more of this one.
Related: why I don’t think travel is frivolous.
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