[ TIPS · THE DISPATCH ]

Why I Now Plan Every Trip Backwards (And You Should Too)

Most people start with a destination, then dates, then flights, then panic. I start with the one thing I'd most regret missing, then build the trip around that. The difference is enormous.

I spent years planning trips the normal way: pick a destination, find cheap flights, book accommodation near something famous, then figure out what to actually do once I got there. This produced fine trips. Trips I enjoyed. Trips that also had a weird formless quality, like I was improvising in a city that was only partially paying attention to me.

Then I got waitlisted for a table at Noma in Copenhagen — back when it was still open and you had to plan six months ahead — and I spent four months working backwards from that single dinner to build a trip around it. The flights, the dates, the surrounding days, the whole thing — all arranged in service of one anchor event. It was the best trip I’ve ever taken. The meal was extraordinary; everything else I planned more carefully because I’d started from what mattered most.

I’ve planned backwards ever since.

The conventional planning sequence goes: destination → dates → flights → accommodation → activities. It’s logical but it has a flaw: you choose the dates first, which means you’re choosing availability-first and experience-second. You end up in Kyoto during the wrong season because that’s when flights were cheap, or in Edinburgh during a festival you didn’t want rather than the one you did.

Backwards planning reverses this. You start with the experience you most want to have, then derive everything else from it.

1. What’s the thing? The one experience, place, event, or feeling that defines why you want to go at all.
2. When is that thing best/only available? This determines your dates. Not the other way around.
3. Given those dates, what does accommodation look like? Now you know when you need to book.
4. What flights serve those dates at reasonable cost? Now you’re searching with purpose.
5. What else is worth doing, given you’re there at that time? Fill in the rest around the anchor.

Planning order	What it optimizes for	What it sacrifices
Conventional (dates first)	Flight price, convenience	Timing, seasonal fit, experience quality
Backwards (experience first)	The thing you most want	Some price flexibility on flights
Hybrid (experience → dates → price check)	Balance of both	A bit more planning effort upfront

The hybrid is what most experienced travelers land on. “I want to see the cherry blossom in Kyoto” is your anchor. Cherry blossom peaks late March to mid-April, with variance by 7–10 days depending on the year. Now you book a flexible-ish flight window in that range and watch prices. You’re searching with purpose instead of browsing.

The anchor doesn’t have to be a famous event. It can be:

• A specific restaurant with limited availability
• A seasonal phenomenon (cherry blossom, Northern Lights, a specific festival)
• A timed attraction (some museums have timed entry that books out months ahead)
• A physical window (the Sahara in spring before it gets brutal; the Alps in July before the August crowds)
• A personal goal (“I want to hike the Cinque Terre trail when it’s not 38°C and rammed”)

If you don’t have an anchor, that’s fine — but then be honest that you’re doing a flexible-format trip and plan accordingly. What backwards planning really does is force you to think about what you actually want before you’ve committed to dates.

Better timing. This sounds obvious but most people visit places slightly out of season or slightly wrong for the experience they wanted — not by choice, but by default. Backwards planning fixes this.

Fewer “we should have come in spring” moments. You know, the one where you’re standing in front of the famous lavender fields of Provence in July and they’re already done.

Bookings that don’t collapse. When your core anchor is booked first, everything else is flexible. If a restaurant falls through, you’ve lost a nice-to-have, not the structural reason you came.

Less decision fatigue. Having an anchor gives every other planning decision a filter. “Does this hotel location serve our time at the anchor?” is a better question than “which hotel looks nicest on a map?”

What if I don’t have a specific anchor and just want to go somewhere new? Then your anchor is a season or a rough feeling: “I want to be somewhere warm in March” or “I want to see autumn colour in October.” Use that to narrow the destination rather than picking a destination and hoping the timing works.

Isn’t this more work? Slightly more upfront, yes. But it replaces the panicked scramble of “now I have flights, what am I actually doing there?” with a plan that already has a backbone. Net effort: lower.

What if the anchor is expensive and I can’t afford it? Find a different anchor, or save until you can. A trip built around something you settled for on the core experience is just a trip built on compromise from the start. The anchor is supposed to be the thing you’d actually regret missing.

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