We are a family of 4: 2 adults and 2 sons (18 and 14 years old). We are going to travel in northern Italy for 10 days. We will be in the Dolomites for 5 days and we would like to visit Tuscany for the second part of the trip. We are trying to find a cool farmhouse to stay. We do not know which are of Tuscany to choose from. We would like to be close to a true Tuscany hill town. Any suggestions?
Tuscany is a region of farms mainly growing wine grapes and olives. Some also make wines and/or olive oil of various quality. Since the farms are small, virtually every farm in the area has apartments and/or rooms for rent as a secondary source of income.
We last stayed between Certaldo and San Gimignano, and it's a good area for touring the countryside. There were literally hundreds of places to stay close by. We were NW of Poggibonsi and no more than 25 miles south of Florence.
Villas.com has 5818 properties in Tuscany listed. Booking.com is another great reservation website. AirBnB.com covers the world, and they have many Tuscan property listings. You can even go onto Craigslist.com and fine perfectly decent accommodations. Agriturismo.com has many listings. You first need to decide where you'd like to stay.
You can also go on GoogleMaps.com for a specific city and hit "+++" to magnify the map. B&B's and agriturismos will have icons to click on that shows pictures and links to their direct web site.
And when in doubt, read some of the good travel guides, like Rick Steves' Italy, that show accommodations.
Good luck on your search. It's a region best seen via auto. We especially enjoyed Orvieto, San Gimignano and Volterra.
You should check out Cretaiole near Pienza. We will be there in 10 days. It is our second visit. Isa is an amazing hostess and the experiences she arranges in the area are amazing.
Look up Casa Ercole outside Panzano and near Greve in the beautiful Chiant Classico region. We have stayed with Alda several times and have sent several friends there, all of whom loved it. Contact me offline and I can tell you more.
As you read through Rick's book, you'll probably need to read the whole hilltowns chapter to find any agritourismo listed; there is no easy index or map of those.