Tuscany, Twenty Two People, Six Nights

This is an example journey, composed from the way we build trips of this shape rather than from one identified client. The decisions in it are the real ones.

Know before you go

• The shape: twenty two people, three generations, six nights, two houses.
• Lead time: nine to twelve months for September in Tuscany. Six is workable, shorter is possible.
• Settle early: one house or two, who cooks and how often, and the arrival windows.
• What drives the cost: villa size and staffing, vehicles, and private guides rather than the nightly rate.
• Where it usually goes wrong: arrival day and the last morning.

The brief

A sixtieth birthday. Twenty two people across three generations, six nights in September, somewhere in Tuscany. The host wanted everyone under one roof and a week that did not feel organised.

We talked her out of the first of those and delivered the second.

Two villas, nine minutes apart

One house that sleeps twenty two exists. It is almost never the right answer. At that size you are choosing between a property built for weddings, which feels like a venue, or a compromise where four people end up in rooms nobody would pay for.

Two houses nine minutes apart solved it. The larger one took fourteen, including everyone who wanted to be where the noise was. The smaller took eight, including both grandparents and the couple with a toddler who needed to be able to leave dinner at eight without it being an event.

Everyone ate together. Nobody slept together. That distinction is most of what makes a group week work.

Arrivals across two days, into two airports

Twenty two people do not land at once. Nine came through Florence, eleven through Pisa, two drove down from Milan. Spread over two days because a single arrival day means either half the group waits or you run four vehicles at four separate times anyway.

Both airports were met. Every arrival had a name, a number and a driver who already had the address. Nobody stood in a hall with a phone.

A cook for four of the six nights

The instinct is to book a cook for every night. It is a mistake. By night five a group wants to go out, or wants to make pasta badly and drink too much without anyone in the kitchen.

Four nights in, two nights out. One of the two out was walkable from the larger house, because at the end of a long day nobody wants a twenty minute drive to dinner. The other was worth the drive and was booked eleven weeks ahead.

Vehicles sized so nobody waits

The maths people get wrong. Twenty two people is not one coach. A coach cannot get up most of the roads these houses sit on, and it turns every outing into a departure time everyone has to meet.

Three vehicles, two of them eight seaters, kept the group flexible. The vineyard afternoon ran as two waves an hour apart, which meant the people who wanted a slow morning got one and the people who wanted to leave at ten did.

The bedroom that matters

In every group of this size there is one room that carries meaning, and one person it should go to. Here it was the corner room in the smaller house with the view the host had described from a trip thirty years earlier, and it went to her mother.

Nobody discussed it. That is the point. Somebody decides these things in advance so the group never has to.

What we would change

The first night should have been simpler. We put a cook on it, and after a day of flights the group would have been better served by a table of cold things and an early night.

We would also have moved the vineyard from day two to day four. Groups need a slow start more than they think they do.

Planning something similar?

If you are looking at a week for a group, see how we handle group travel, or tell us the dates and roughly how many people. We will come back with a shape and an honest view of what it costs.