Tuscany villas for 14 guests

At fourteen, you are choosing a region as much as a villa

This is the honest thing about this size, and it is not true at eight or ten. Very few Tuscan villas sleep fourteen properly, so the ones that do are scattered rather than evenly spread — and in our collection the largest share sit around Lucca and the Garfagnana, in the north-west, including two borghi that take twenty-four. The rest are spread thinly across Chianti, the hills near Siena and the Maremma, which means the shortlist at this size is short wherever you look.

The practical consequence is that a party of fourteen usually ends up in the north-west whether or not that was the plan, which is a good outcome if you want Florence, Pisa, Lucca and the Versilia coast within an hour, and the wrong one if the week was built around Siena and the Val d'Orcia. Decide that before you fall in love with a villa. Our seven-day itinerary sets out what each base actually gives you.

One villa, or two next door

At fourteen there are two shapes of answer and they suit different groups. A single large villa keeps everyone under one roof, which matters for a milestone birthday or a family that wants to eat together every night. Paired properties on the same estate give each family its own front door, which matters when the party spans several generations and different bedtimes.

We hold both. Several estates have two or three villas within walking distance, so a group of fourteen can take a main house for the cooking and the long table and a second for sleeping. It is often cheaper than the single property large enough to hold everyone, and it is almost always more comfortable. Tell us the shape of the party — how many couples, how many children, who needs to be near whom — and we will tell you which of the two suits it.

What to check before you commit

Bathrooms first: fourteen people getting ready for dinner needs six or more, and the difference between six and four decides the mood of the week. Ask for the count, not a photograph of one of them.

Then the table. A villa can sleep fourteen and still have a dining room that seats ten, which means the group splits every evening — the single most common complaint at this size. Ask where fourteen people actually eat, indoors and out, and ask what happens on the two wet days a week in May or October reliably produces.

Then staffing. At fourteen, self-catering the whole week stops being a holiday for whoever volunteers. Most groups take the villa cook for two or three evenings and a chef for one; a three-course dinner runs about €90 an adult and €35 a child at our villas, which is roughly restaurant money without the drive. The staffing guide sets out who comes with the villa and who is arranged separately.