Where to stay in Tuscany


New member

I'll go with my girlfriend and parents to Italy in September. We will land in Milano, get our rental car, and likely start the tour by heading towards the Como Lake. After a few days there (I think) we'll head to Tuscany, but as its our first time in Italy, we are clueless as where to stay.

Ideally we would like to stay in the countryside, but with good areas within driving distance. Our plan is to spent some days just relaxing at the pool, and other days on the road to see Tuscany.

So, what areas should we look at?


The Tuscan Expert ;-)
Staff member
Ciao wildjack,

The best areas to base yourselves in for driving around Tuscany are actually pretty wide, since most of the sights to see are all within 2 hours of each other.
But to be really central, I'd recommend anywhere in the area between Florence and Siena which is the area known as Chianti... and it is pretty wide sideways... to the west to San Gimignano and east to Arezzo... anywhere in that wide circle and you are within easy driving distance of most places.

September is still a very popular month so don't expect to come without booking ahead of time - the farmhouse and villa apartments generally are rented by the week, those run as a hotel or B&B are the ones that offer stays of less than a week.

To get your search started on where to stay, I'd say to start from here:
It has a mix of different accommodations, from entire villas to rooms to apartments.

Another good area to stay in is right to the south of Siena - take a look at these:
If you stay in this area, a day trip to Florence is about an hour and a half drive away, just because you do drive on the smaller regional roads until you get to Siena from which you can catch the A1 on the east or the Firenze-Siena to the west.

Beautiful day trips would include Florence, Siena, San Gimignano, Volterra, Certaldo, a drive through Chianti with stops in Castellina in Chianti, Radda in Chianti, Panzano in Chianti and Greve in Chianti.... you will definitely want to spend as much time here as you can ;-)

Hope this gets you started - feel free to post any other questions you might have as you start your search!