The trip you actually want

People plan trips from lists of things to see, which produces itineraries that are defensible and frequently not what the person wanted.

The question nobody asks

What do you actually enjoy?

Not what is worth seeing, or what you should see, or what other people enjoyed — what you specifically find rewarding.

Most people can answer this once asked and rarely ask themselves, which is why so many itineraries are assembled from consensus rather than from preference.

The evidence you already have

Look at previous trips.

What do you actually remember? Almost certainly not the third museum.

What did you enjoy at the time, as opposed to what you felt you should have enjoyed?

What did you resent doing?

Where did you feel most engaged, and what were the conditions — alone, with people, walking, sitting, eating, moving, still?

The answers are generally consistent across trips and are rarely acted on.

The common patterns

People tend to fall into recognisable types, and knowing which you are changes what to plan.

Some people want to move, and are happiest covering ground.

Some want to settle, and are happiest becoming familiar with one place.

Some are led by food, and organise everything else around it.

Some by landscape, and are indifferent to cities.

Some by people, and enjoy anywhere provided there is contact.

Some by activity, and need something to do rather than to see.

Some by rest, and want a good chair and few obligations.

None is better, and planning against your own type produces a trip that is uncomfortable for reasons that are hard to identify at the time.

The things people do because they think they should

Worth naming.

Visiting the principal sight because not visiting it would be strange.

Museums, when the person does not particularly like museums.

Covering multiple cities because the flight was expensive.

Nightlife, when the person would rather sleep.

Organised tours, when the person would rather walk.

And keeping a schedule because the planning was done.

Every one of these produces a day that is fine rather than good, and the accumulation is what makes a trip forgettable.

The permission worth giving yourself

Explicitly.

You are allowed to skip the famous thing.

You are allowed to return to the same restaurant three times.

You are allowed to spend a day doing nothing.

You are allowed to leave somewhere early because you are not enjoying it.

You are allowed to go back to a place you have already been rather than somewhere new.

Each of these is obvious and each is routinely overridden by a sense of obligation that comes from nowhere in particular.

The planning method that follows

Start from the type of day you want, not from the destination.

Identify two or three things you genuinely want to do, and build around them.

Leave the rest open.

Choose a destination that supports the days you want rather than one that has the most attractions.

And plan for fewer things than the time appears to allow, which is the consistent advice from everyone who travels frequently and the consistently ignored one.

The test afterwards

A useful practice.

After the trip, note what the best day was and what made it so.

Over several trips, the pattern becomes obvious, and planning against it becomes straightforward.

Most people find that the best days were unplanned, involved one thing rather than several, and had a substantial amount of walking, eating and sitting in them.

Which is worth knowing, because it is entirely possible to plan for.

Travelling with other people's preferences

A complication worth naming.

Where a trip is shared, the itinerary generally reflects a compromise that satisfies nobody fully.

The approach that works better than compromise is division: each person gets some days that are theirs, and the shared days are the ones both actually want.

Which requires stating preferences explicitly rather than deferring, and produces a better trip than an averaged one.

Changing your mind

Permission worth giving yourself.

If a place is not working, leaving early is available and is generally the right decision.

People who travel a great deal do this routinely, and people who travel occasionally almost never do, which is the difference between an itinerary and an obligation.