Tuscany is always wonderful place to take the family on holiday - there is plenty to do and explore for all ages, and swimming pools for when the exploration is done. But it need not just be parents and children: a recent study found that seven in ten families have chosen to holiday together, from kids to grandparents.

We are big fans of the multi-generational holiday, when the whole family goes together. It's a great time to reconnect, enjoy some time together and give the grandparents some quality time with the little ones. And perhaps give the parents a little downtime too.

We've seen a big rise in these kind of holidays in the recent years and have a selection of large family villas that suit this kind of family gathering. Here are our best five multigenerational family villas in Tuscany:

1. Docciole

By a village and with an enormous garden

Docciole - Sleeps 12 in Chianti
Docciole - Family Villa in Chianti, Tuscany
This is a large old stone farmhouse in Chianti, a classic Tuscan villa. It was converted by the owners, who normally live in Rome, to be their 'multi-generational family country retreat' and they put a lot of thought into what makes a family get-together work, including recognising that sometimes we all need a little 'alone' time. For this reason the lower floor bedrooms are all set up as little independent suites, with their own bathrooms and little kitchens - if you want to have breakfast alone, then this house is set up for that.

Conversely, when you are all together, eating and cooking are great social occasions, so the upstairs living room and kitchen are enormous, perfect for large meals together. In summer, Tuscan life moves outdoors, so there is also an outside kitchen, including a fabulous "Heath Robinson-like" clockwork barbecue, set next to an table under a pergola clad in vine leaves.

Radda in Chianti
Radda in Chianti
Lastly, it is within walking distance (half a mile) of Radda in Chianti, the self proclaimed capital of the Chianti region of Tuscany. There are restaurants, shops and most importantly, ice-creams in Radda, all without having to get everybody in a car.

The last review, from UK clients:

"We absolutely loved our time at Docciole. You will be welcomed by lovely Anna who’s family home it is. It is a typical Tuscan stone farmhouse with a lovely homely feeling and loads of space for living inside and out. We particularly enjoyed the outdoor kitchen under a grape vine pergola and the swimming pool surrounded by olive trees. It is exceptionally well equipped for cooking and eating Anna is a perfect host and responded to the small issues that cropped up. It is a short walk to charming Radda in Chianti with spectacular views across Tuscan countryside, some tourist shops and a useful Coop supermarket. It is perfectly situated to explore the Chianti region if you’re into wine, medieval villages or the spectacular Sienna and Florence. Can’t recommend it highly enough!.

Show me Docciole!

2. Pietrina

A family villa near Arezzo and Cortona

Pietrina for 10 in Tuscany
A sketch I made of Pietrina in 2022
Pietrina is a beautiful villa for 10 set on one of the finger ridges coming down from the Apenine mountains of Vallombrosa. The pool has fabulous views and the house has been lovingly restored by the English owners - it is a special place.

This is a review from guests in 2021:

"We spent a wonderful time at Pietrina that is situated in a very panoramic position close to San Giustino Valdarno. [...] There is a lovely terrace on the front side of the house with a generous BBQ station from which you can look at the ample olive grove and the Pratomagno with its heights and woods and another place where to eat and dine under magnificent old oaks looking to the other side, the hills and fields of the Arno valley. Not to forget the sumptuous pool area with enough space to be able to play crocket or KUP (our passion). All this is beautifully arranged with lots of flowerbeds gradually ascending versus the woods. [...] The situation at the end of a little valley makes Pietrina a very peaceful retreat, sometimes you will see at dusk some boars coming down to the olive grove, a tame fox showed up asking for a goodie which we refused of course because it has to learn to survive in the wilderness. However, it was extremely sweet. A lasting impression is that this is a very natural and authentic neighbourhood (the next neighbours are not very far away). In fact, we got to love this region that seemed to us not at all as touristy as the Chianti or Crete Senesi and offering a great quality of life. Arezzo is stunning and Florence is not too far to visit for a day.

A perfect spot for a family holiday.

Pietrina sounds perfect for us

3. Dimora

A sprawling one floor villa where every door opens onto the garden.

Dimora Villa for 12 in Chianti Vineyard
Dimora Villa for 12 in Chianti, Tuscany, Italy
This villa for 12 is set in the vineyards and olive groves of a large Chianti wine estate. The estate is run along strict bio-organic rules and when the Estate owner converted this villa he decided to make sure the house would be as ecological as he could make it, with solar panels for electricity and rainwater collection. This is a great choice if you're trying to green your holidays.

It's also a great choice if you love wine - you can buy the excellent wine produced by vines a few feet from your door and the owner will give you a guided tour of his wonderful cellars in nearby Barberino Val d'Elsa.

Like Docciole, this house also has a fabulous barbecue and lots of spaces for outdoor living, playing and dining.

Famous wine estate? Dimora it is

4. Amorosa

Swimming pool, Tennis court and endless views.

Amorosa Villa for 14
Amorosa Tuscan Family Villa for 14 near Siena
Occasionally we will see articles about Tuscany being crowded: Amorosa will promptly reveal how untrue this is. Tuscany has several large parks plus a large number of protected areas (I've just counted over 70), generally called "Riserve", that are smaller than the parks but no less beautiful.

Villa Amorosa is on the edge of the "Riserva di Berignone", an area of over 2,000 hectares (around 5,000 acres) of hills covered in dark holm oaks, with streams, caves, castles and long paths hidden within. This gives the house fabulous views and, for the more adventurous, amazing possibilities for exploring. If you drive to the end of the track that goes past Amorosa, you will find an old house and the road barred. Leave the car and walk from here - not too distant is an old Castle, once owned by the Bishops of Volterra, set on a cliff over the river Sellate.

If you prefer to simply enjoy the view the house has a wonderful fenced pool, a tennis court, a children's playground and a ping-pong table. A perfect villa for relaxing family holidays.

Far from the crowds, perfect! show me Amorosa

5. Valdambra

A sprawling ex-farmhouse with 3 apartments and a great pool

Farmhouse Villa with a large private pool
Family fun in the big pool at Valdambra

The owner of this beautiful old farmhouse converted it carefully into three apartments that work very well when taken altogether as one big house. There are hammocks among the trees, corners to relax in, wonderful restaurants and places to explore nearby this villa that seems designed to slow down our busy lives.

Arezzo and Siena are both within easy reach, as are smaller hill villages like Civitella in Val di Chiana, or Monterchi.


Valdambra family villa for 10-16
Villa Valdambra in Tuscany