How many days do you need in a city? How I decide now

Someone asked me last month how many days you need in Tokyo. I gave them a number, then took it straight back, because the honest answer depends far more on them than on Tokyo. How many days do you need in a city is one of those questions that sounds like it has a clean answer and doesn't. I have spent the last few years working remotely and slow-travelling across Korea, Taiwan, Japan, Thailand and Indonesia, and if there is one thing I have learned about trip length, it is that the same place can want three days or three weeks depending on who is asking.

So this isn't a listicle telling you Rome needs four days and Lisbon needs three. Those numbers are guesses dressed up as facts, and they will fit some people and quietly ruin the trip for others. What I can give you is the way I actually decide now, after getting it wrong in both directions more times than I would like.

Why there's no fixed number of days for a city

How many days do you need in a city has no clean answer, because a city isn't a fixed amount of stuff to get through. It is a place you move through at your own pace, with your own tolerance for slow mornings and your own idea of what counts as having seen somewhere. Two people can spend the same four days in Seoul, and one comes home saying it was rushed while the other was bored by day three. Same city, same days, completely different trips.

Ask ten travellers how many days you need in a city and you'll get ten answers, all of them right for the person giving them. A few things move the number far more than the city itself does. How fast you like to travel. Whether you are there to see the sights or just to be somewhere for a while. Whether this is your one shot at the place or somewhere you could easily come back to. Get honest about those three and the right length starts to show itself.

Working while you travel changes the maths

Here is the part that caught me out for a long time. If you work while you travel, a week in a city is not a week in the city. I might book ten days somewhere and spend six of them mostly at a desk, which leaves four to actually be there. So the number I need isn't how many days does this place want. It is how many free days do I want, and then I add the working days on top.

When I first started this I would book what looked like a generous stay, a fortnight in Chiang Mai, and then feel cheated that I hadn't seen much. The stay was fine. I had just forgotten that half of it was going to be work, the same as any other fortnight. Now I count a trip in free days rather than total days, and most of that disappointment went away.

Count a trip in free days, not total days. A fortnight where you work half of it is one good week in disguise.

How I decide how long to stay in a city now

So how many days do you need in a city? These days I don't answer with a number. I run through a short list of questions instead. None of them is clever. Together they get me close enough.

• Is this a base or a stop? A base is somewhere I settle, work from and use for day trips, and that easily earns a week or two. A stop is a place I pass through for the two or three things it's known for, and three or four days usually covers it.
• How much is actually here versus nearby? Some cities are the whole trip. Others are a small centre with the good stuff an hour out, which means day trips, which means more nights even though the city itself is small.
• What is my real pace? If I know I want a slow coffee and a walk before anything starts most mornings, I add days or accept I'll see less. The plan where I go hard from 8am never survives contact with the actual trip.
• Will I come back? Somewhere I can reach again easily, I undershoot on purpose and leave wanting more. A once-in-a-decade long-haul trip gets the extra days, because regret costs more than a slightly long stay.
• What's closed when? A place can need an extra night purely because the one thing you came for runs on certain days only, or shuts for a weekly rest day you didn't clock.

That last one has burned me enough times to earn its place. I've built a stay around a market or a museum and found out on arrival that it doesn't open the days I'm there, which is the kind of small miss that colours a whole trip.

Too few days and too many days both cost you

Both ends go wrong in their own way, and it helps to know which mistake you lean towards. Too few days and the trip becomes a forced march. You're changing hotels every second morning, never off the main track because you never have a spare afternoon, and you spend the whole time slightly behind. I've done city-a-day stretches and remember almost none of it, just a blur of stations and dragging a bag up stairs.

Too many days in a place with not much to hold you is its own kind of flat. The first two days are lovely, then you're walking the same three streets wondering why you're a bit bored in a beautiful city. For me the sweet spot leaves on a slight high, with one thing still unseen, rather than staying until the place goes stale. Frictionless travel, if there is such a thing, is having enough time to not rush and not so much that the days start to sag.

A rough starting guide (then ignore it)

If you genuinely just want a number to start from, here is the rough shape I use before I adjust for everything above. Treat it as a first guess, not a rule.

• A small town or a single sight: one to two nights. Long enough to see it without the day turning into a checklist.
• A mid-size city: three to four days. Enough for the main things and a bit of wandering, without dead time on your hands.
• A major city you actually want to know: five to seven days, more if you're working. Big cities reward a slower second pass, going back to the neighbourhood you liked the first time round.
• A base for day trips: a week or two. You're not counting the city's own sights so much as buying a comfortable spot to work and explore from.

Then change all of it based on your pace, whether you're working and whether you'll be back. The number is a starting point you're meant to argue with, not a target to hit. If your gut says a place wants longer than the guide, your gut has usually met you before.

I still get it wrong. I over-booked a quiet coastal town in Indonesia earlier this year and spent the last three days working just to fill them, which is a daft way to be somewhere that lovely. But I get it wrong less than I used to, mostly because I stopped asking how many days a place needs and started asking how many days I need there. Wherever you're headed next, I'd lean towards slightly too few over slightly too many. Leaving with a reason to come back has never once let me down.

If you take one thing from this, make it the free-days count. Work out the days you actually want in the place, then add on the ones you'll spend at a desk, and book from that number.

Benjamin

Founder & sole developer, Novaire Digital