Well maybe the kind of holiday that most suits you is a farming-working holiday! There are a few web sites that help volunteers find a place that most fits their needs. Here you find a small selection of them, feel free to comment this post and add more!
Farming working holiday/Free accommodation in Tuscany sites:
I would also like to add a direct link to Spannocchia.org, an example of a local farm that also offers workshops in Italian language, literature, art, crafts, Tuscan cooking and sustainable farming. In exchange they require workers to help with the farming chores, grow vegetables, feed and care for the animals, or just lay by the pool and enjoy the fruits of a working farm.
If you want to have a direct feedback from someone who actualy travelled like that, here’s Peter Munro’s experience in Montepulciano, written for the timesonline:
“The fresh food is reward enough for gathering stones, or the sting on my hands from pulling nettles out of a tainted English lawn. On a 45-acre farm near Montepulciano, where our room is a converted cow shed, handfuls of artichokes, beans, leeks and lettuce, rosemary, sage and wild mint travel only from the garden bed to the kitchen. The food is so fresh that it needs little seasoning. Vegetables are served with oil and salt, melted into a ribollita (bean soup) or fried with pasta, basil and onion in a sauce squeezed from home-grown tomatoes. Salami, speck and ham hang from the rafters of the 15th-century farmhouse like a clothesline of crusted socks. On the wood table are nine-pint bottles filled with wine from last season’s vendemmia, or grape harvest.
Barbara Mariotti, who was born in Queensland, learnt some of her recipes from the old women of the nearby spiralling stone city of Petroio, while they talked and queued for drinking water at a fountain. The Mariottis have a well now, dug 90yd into the clay bed. There will be a shower and a flushing toilet one day. For now, there is a bucket for bathing, and a hole and a bucket of sawdust for the rest.
We spend long hours at the wood table with Barbara and her husband, Ugo, a native of Tuscany; both are former residents of Paddington. We eat honey with pecorino cheese from a factory near a wooden bridge in Pienza, drink grappa from Montepulciano and talk about grapevines and death and how hard it can be to love your family.”
To better understand how farming working holidays work, check out this video by wwoof.org:
Moreover, if you’re a sea lover, through the find a crew web site you have good chances to find a crew to sail with. Free accomodations and food in exchange of some help on board. (I just checked and there are a few boats heading to Tuscany as well )