Three Generations, One Villa: Making Crete Work

Three generations, one villa, one week. It is the fastest-growing shape of family holiday and the one most likely to end in a long silence over dinner on the Thursday.

It does not have to. But the villa listing will not tell you what actually goes wrong, so here it is.

The mistake is trying to do everything together

Almost every difficult multigenerational week has the same cause: someone has planned it as one group doing one thing at a time.

That works for about two days. Then the eight-year-old wants the pool, the teenager wants wifi and to be left alone, the grandparents want a slow morning and a proper lunch, and the parents want ninety minutes in which nobody asks them for anything. Forcing all of that into a single itinerary means every day is a negotiation and somebody is always the one who gave in.

The fix is structural. Plan for the group to split most days and converge in the evening. Two cars, not one. Nobody apologises for opting out of the gorge walk. The day belongs to whoever wants it; the evening belongs to everyone.

What to actually check before you book

A villa agency's own guidance on this is worth reading, with the obvious caveat that they are in the business of letting villas. Their practical points are sound, and they are the ones photographs hide:

• Unfenced pools, open staircases and steep paths. Greek villas very often have all three. Photographs make a lethal drop look like a charming terrace.
• Is there a bedroom on the ground floor? If a grandparent has a bad hip, a beautiful house with the only spare room up an open stone stair is not a beautiful house.
• The exact distance and route to the nearest shop, beach and taverna. Not "10 minutes" — ask for the road.
• How the bedrooms and bathrooms are arranged. A villa that sleeps eight may be perfect for two families sharing and quite wrong for four couples who each expected a door that shuts.

And ask the owner directly rather than only through the platform. The written description is more honest than the gallery.

Above about twelve people, book two villas

This is the advice most likely to save your week and least likely to be given to you by anyone selling accommodation.

One enormous villa for fourteen or sixteen sounds efficient. In practice you get one kitchen, one set of bathrooms, one sitting room and no way for anyone to be quietly out of the way. Two smaller houses near each other — even a five-minute walk apart — gives every family a retreat and still gives you a shared pool and a shared table. Groups that do this argue less. It usually costs about the same.

The evening is the bit that has to work

If the day is deliberately fragmented, the evening has to pull the week back together, and eating out every night will not do it. With three generations you are looking at a table booking for twelve, two cars, a designated driver, and small children melting down at ten o'clock. Twice is lovely. Seven times is a rota.

So plan two or three evenings that happen at the villa. We have written up fifteen of them, and a cinema night is one — a screen on the terrace, everyone in one place, nobody driving. The Gathering is €850 for up to fourteen guests, with additional guests at €60 each. We set up around six and collect at midnight, and all we need is a mains socket; the twenty-metre extension cable means the screen goes where the view is.

Two things not to do

Do not book it for arrival night. People land tired, the shopping has not been done, and somebody's luggage is in Athens. Wednesday or Thursday is the right night, when the group has found its rhythm and is starting to fray.

If your youngest are under about five, do not book a cinema evening in July or August at all. The sun does not set until around 20:20 in early August, so the film cannot start before roughly half past eight — which is a small child's bedtime with the volume turned up. Either come in late September, when it is dark closer to eight, or spend the money on something they will actually be awake for. We would rather tell you that now than take the booking and watch you carry a sleeping four-year-old inside twenty minutes in.

If the children are seven and up, none of that applies and it is one of the easiest evenings of the week.

The short version

Split the days, share the evenings, book two houses if you are more than a dozen, and check for the fence around the pool before you check the view.

Planning a group week? Tell us the villa and the dates and we will tell you honestly whether we suit your group — including if we do not.