Going on holiday with another family? Sort these out before anyone books

Olive groves around Vasilika, in the northeast of Corfu.

Sharing a holiday with another family looks like easy maths: one big house, half the cost each, and the children get ready-made friends for the week. The trips that go wrong rarely come unstuck over the weather, though. They come unstuck over money, bedtimes and who is driving back from dinner.

Most of it can be settled over a cup of tea at home, well before anyone pays a deposit. Corfu makes a useful example to plan around, because holiday villas in Corfu range from one big house where everything is shared to estates split into separate homes, and that choice shapes nearly everything else here.

Agree how the money splits, and put it in writing

Settle the split before you look at a single listing. Per family sounds fair until one household is two adults and a toddler and the other is two adults and three teenagers who each want a bedroom. Per head is usually easier to defend, with small children counted at a reduced share if everyone agrees.

The awkward questions are the ones worth asking out loud now:

• Who pays the deposit, and what happens to it if one family has to drop out?
• How do you share the food shop and the meals out, a kitty or a running tally on a shared expenses app?
• Does anyone pay a bit more for the biggest bedroom or the one with the best view?
• Does everyone have travel insurance that covers cancellation from the day you book?

None of this is romantic, but a short message with the answers saves a lot of quiet resentment by Thursday.

Look at the layout before you look at the pool

The floor plan will decide more about your week than the photos will. One large villa usually means one kitchen, one living room and one set of stairs, which works brilliantly until a two-year-old needs to sleep at seven and the teenagers want the sofa until midnight.

Count bathrooms against people, not bedrooms. Eight guests sharing two bathrooms makes for a very different morning from eight guests with four. Then check where the bedrooms sit. If both families end up on the same landing, every early riser wakes everyone else.

Outside space matters as much as rooms. In a Greek summer most of the day happens on the terrace, so look for proper shade over a table big enough for everyone. A quiet corner where a small child can nap away from the pool noise helps too.

Search for villas in Corfu with private pool and most results are a single house with a single pool. That suits two families who already holiday together easily. If you’re less sure, look for a property built as two homes on one plot.

Two homes on one plot, how that looks in practice

The Ionian Stone Estate, in Vasilika in the island’s northeast, works this way. Its two villas share 6,570 square metres of olive grove, and each one runs to 205 square metres, four bedrooms and four bathrooms, with an entrance of its own. Each also has a private 32 square metre pool, a hot tub and an outdoor kitchen with a barbecue. Together they sleep sixteen, yet each family keeps a kitchen and a living room to itself.

Each villa on the estate has its own pool and hot tub.

In practice the two families can spend the afternoon around one pool, cook together on the barbecue when it suits them, and still shut separate doors at night. Nobody has to tiptoe past a sleeping toddler to fetch a drink from the fridge.

Make a food plan that isn’t one person’s job

Shared cooking is where goodwill tends to run out first, usually because one parent ends up doing all of it. Agree a rota before you fly. A simple version is breakfast and lunch in your own family’s space, then a shared dinner that each household takes in turn, with a couple of nights out in between.

An outdoor kitchen keeps shared cooking out of the heat of the house.

Do one big shop together on the first day so the basics are covered, and keep a list on the fridge for top ups. In the northeast, Kassiopi is 6 km from Vasilika and the obvious place for it. Ask about allergies and fussy eaters now, rather than finding out in front of a grill on the first evening.

Cars, drivers and the airport run

Plan on two cars, one per family. Vasilika, for instance, is 40 km from the airport, the roads into the hills are narrow, and a single car means one family is always waiting for the other. It also means each household can head off on its own schedule.

Book child seats when you book the cars, or bring your own if the airline carries them free, and check the hire company fits them properly. Then agree who drives on nights out. Taking turns is fairer than leaving it to whoever happens to drink least.

Build in time apart on purpose

The best shared holidays usually include days when nobody is together at all. Children of different ages want different things, and a week of doing everything as a group of eight or more wears thin quickly.

Plan one or two days in advance when each family goes its own way. One might take the little ones to the beach at Almyros while the other drives up towards Mount Pantokrator or to Old Perithia, and the two groups swap notes over dinner.

Evenings need the same honesty. Families with young children are often in bed by nine, while others like a late dinner and a drink outside. Agree early on whether shared dinners are every night or a few nights, and let the late crowd go out without anyone feeling left behind.

Before anyone pays the deposit

Most of the trouble on shared holidays comes from things nobody said before booking. Money, sleeping arrangements, cooking and cars cover nearly all of it.

Write the split, the food rota and the car plan in one message to the other family, and book only once everyone has replied to it.