How to plan a trip when you hate planning

1. Decide the shape before the place

Not "where" — how long, roughly when, and how much. Four nights in October for around £1,200 each is a shape. "Somewhere in Europe sometime" is not, and it is why the browser tabs multiply.

The shape eliminates most of the world instantly, which is the point. A long weekend rules out anywhere more than a few hours away. A tight budget rules out peak weeks. You have made progress without choosing anything.

2. Pick the destination in one sitting

Give yourself a shortlist of three that fit the shape, and choose within the hour. The difference between two good destinations is far smaller than the difference between going and not going, and every extra day of deliberation costs you real money in airfare.

• Prefer somewhere direct if the trip is under five nights — a connection eats a whole day at each end.
• Check what the weather does at your dates before you fall in love with photographs from another season.
• If two people are choosing, each names one veto and one must-have. That resolves it faster than discussion.

3. Book transport first, and let it set the itinerary

Flights and trains are the least flexible and most price-volatile part of the trip, so they go first. But choose them for the shape of the day, not just the fare: a 6am departure and an 11pm return look like a bonus day and usually deliver two ruined ones.

Write down your arrival and departure times before you plan anything else. They decide what day one and the last day can realistically hold.

4. Choose accommodation against your plans, not in isolation

This is where most trips quietly go wrong. A place is not cheap if it costs you an hour of transit a day and a taxi home every night. Before you book, list three or four things you know you want to do and check where they actually are.

The right question is not "is this a good hotel?" but "is this a good hotel for the trip I'm about to have?" A slightly worse room in the right neighbourhood beats a better one twenty-five minutes out, almost every time.

5. Plan a spine, not a schedule

For each day, pick one anchor — a museum, a hike, a long lunch, a neighbourhood — and let the rest of the day form around it. Group anchors that are near each other on the same day; that single habit removes more wasted time than anything else.

Book only what genuinely sells out: timed museum entries, the one restaurant you care about, anything with a ticket. Everything else can be decided that morning, and should be.

• One anchor per day, two at most.
• Leave one afternoon completely empty. You will need it, and it's the day people remember.
• Put the most physical thing early in the trip, not on the last day.

6. Do the money once, honestly

Add up the four numbers that matter — transport, accommodation, food per day, activities — and then add roughly 15%. Trips overrun on small things: taxis when it rains, one nicer dinner, tickets you didn't plan for.

Decide up front what's shared and what isn't. Groups fall out over splitting after the fact, almost never before.

The part worth outsourcing

Decisions one, two and six are yours: they're about what you want and what you can spend. Three, four and five are research — comparing options, checking what's near what, sequencing days sensibly. That's the tedious part, and it's the part a good assistant can simply do for you.

If you're short on time

• Two weeks out: pick a direct destination, book transport tonight, and accept that accommodation choice matters more than price at this point.
• Booking for a group: agree the budget ceiling and who shares what before anyone opens a booking site.
• No fixed dates: let price choose. Flexible-date search across a month routinely halves the fare.