Basecamp in Tuscany

I prefer the countryside 20-30 miles south of Florence, and north of Siena. The roads are well paved, but a little crooked. Good road signs points you to the different towns in the area.

We stayed between Certaldo and San Gimignano at an agriturismo. Virtually every farm in the area has apartments and rooms as a secondary source of income, and the 2 bedroom apartment with a kitchen we stayed in was very reasonably priced @ 70 Euros.

Poggibonsi has two great modern supermarkets.

It was an easy 5 minute run up the hill to San Gimignano--best seen after all the tour buses leave in the afternoon. We also enjoyed Volterra and Siena--both close by.

In 2011 we stayed outside of Cortona in a farmhouse we rented for the week. We did a day trip to Sienna and Montalpulciano via car, then on our way back to Florence we drove through Chianti. We either ate dinner in Cortona, or enjoyed a dinner picnic with wine by the pool enjoying the sunset. We chose Cortona since it was close to the autostrada, on a train line (took train to Florence twice) and close to a few other hill towns. Seemed like we had a lot of options without spending too much time in a car. Thoroughly enjoyed our week there.

In 2013 we spent 3 nights in Montalcino in a RS recommended hotel and absolutely loved it. But we are into wine, so visited a few wineries in the countryside and Enotecas in the town.

john,
These may help

http://www.slowtrav.com/italy/tuscany/hs_planning.htm

http://www.prolocomontalcino.com/en/events/item/1124-the-festival-of-the-thrush

One of our favorite places to drive around. We usually do it one of two ways. If you want to stay in one place, try a place near Siena. It is central to the places you want to visit, plus Siena is worth a day or two of your time to visit.
More often We do it by staying in 2 places. Many, many to choose from. We like (1) B and Bs around Greve/Panzano to drive around Chianti and to eat dinner in these two towns at night and (2) Montalcino for visiting Southern Tuscany.

Hello John,

I suggest you to take th hill town Cortona as a base. Its central position will make you reach Florence, Siena, Orvieto; assisi in less than 1 hour. Here some suggestions for accommodations: http://www.rentintuscany.it/strutture_ricettive/villas_and_accommodations_rentals_in_tuscany.html
and here for tours or things to do : www.doitintuscany.net

Enjoy your vacation

Federica

Friends of mine (pretty picky bunch) raved about Certaldo. Cooking class for the family, near train station if you decide not to drive somewhere, beautiful old town (Certaldo Alta).