Simon’s travel tips.

If the trip revolves around one restaurant, match or concert, confirm that date before you book the flights. Air schedules usually give you more room to manoeuvre than the thing you actually care about. Build out from the fixed point, then make the days around it worthwhile. The trip will feel deliberate rather than merely busy.

Not every upgrade earns its keep. Spend more when the room changes the experience: the right neighbourhood, a remarkable view, a quiet terrace or service that gives you time back. A larger television and a fancier fruit bowl are not, by themselves, a travel strategy. Pay for what you will notice every day.

A trip can be carefully planned without every hour being spoken for. Keep one afternoon open for the place you hear about over lunch, the shop you pass twice or the simple pleasure of doing nothing somewhere new. Good itineraries need a little breathing room. That is often where the best story begins.

A tight change of planes can turn a good fare into a bad afternoon, especially when terminals, immigration or separate tickets are involved. Give the journey enough room to absorb a late arrival. Starting a holiday with a sprint through an airport is rarely the upgrade anyone had in mind.

After an overnight flight, the clever little hotel across town may be less charming than it looked at home. For the first night, favour a simple transfer, a comfortable room and somewhere good to eat nearby. Save the ambitious logistics for a day when everyone has slept. You can get adventurous again in the morning.

Bring clothes for the weather, the walking and the dinners you have planned, not for an imaginary version of the trip. One dependable pair of shoes is worth several optimistic ones. If something only works with perfect conditions and a forgiving cobblestone street, it can probably stay home. Your feet will thank you before dinner.