Tuscany Recommendations?

I suggest you to sleep in an Agriturismo in the Tuscan countryside, renting an apartment and having daily trips, there are so many places to visit that you really need to make a choice!
The last time I went to Tuscany I chose a place south of Siena (Agriturismo il Molinello, www.molinello.com). For me it was the perfect location as I could reach in 20 minutes Siena, then in less that half an hour the Val d'Orcia, recognized as a World Heritage Site by UNESCO since 2004, visiting Montalcino, Pienza, Bagno Vignoni, San Quirico d'Orcia and Montepulciano. We had an amazing wine tour with Alessandro, the owner, in the Chianti region (we visited either the sienese and florentine Chianti).
The agriturismo is located in the area of Crete Senesi with its unique and picturesque scenery…a spectacular sea of undulating rolling hills like no other in Tuscany.
From il Molinello Arezzo is only 35 minutes far. And in one hour we could also visit Perugia and Assissi in Umbria.
One day we also went to the Trasimeno Lake.
Molly from Finnland

Thank you so much! This is very helpful! If we rent a car, is it hard to drive in Tuscany and is it difficult to find your way around?

I found the Tuscan driving to be pretty easy, and it's certainly the best way to see everything you want. Get a map specifically for the region, such as Michelin Central Italy, instead of a map that covers all of Italy at a smaller scale. When planning your day's drive, it helps to make a list of each town you will travel through, since signs at rural intersections may point more clearly to the next towns than they do to a road number.

alexander,
This may help http://www.slowtrav.com/italy/tuscany/hs_planning.htm

I would suggest you go to the library or book store and get a travel book on Tuscany. After you research the region, come back to this website if you have further questions.

Tuscany is a place that's best visited with a rental car. Trains don't go to all the great hill towns, and buses can be difficult to deal with. You can see far more places by car self guided.

The roads throughout the region are well paved, and easily navigated. We didn't even have any maps, and found our way from town to town with good road signs.

The region is basically rolling hills with vineyards and olive tree orchards--small 20 acre farms are the norm. Virtually every farm takes in travelers at apartments and/or rooms as a source of additional income. We stayed outside Certaldo close to San Gimignano, and we found it very centrally located. That's south of Florence and NW of Poggibonsi about 5 miles.

Have a great trip.

My friends usually rent a car and stop at two, sometimes three towns in a long day. By bus/train, I'm able to visit one.

Note that each person must have an International Drivers Permit in addition to the State Driving License.

Exploring by car is best. Each driver needs an International Drivers Permit (IDP) available for about $15 at AAA. A passport sized photo is required. If you don't have one they can take one for you at AAA. A paper map is required, but a GPS is a big plus.

I agree with the suggestion to stay at an Agriturismo. With 7-10 days you might want to split your time between two different areas in Tuscany. That could allow you to see a larger geographical area without long drives.

Doing a tour in Tuscany isn't necessary, though you could do a day tour of wineries and not worry about having a designated driver. There are so many towns and villages to explore. My suggestion is to read about Tuscany to see what interests you, then plan your days by where they are located. We saw two towns per day. For example, Volterra and San Gimignano pair well together and they aren't too far from each other.

I will add my 2 cents to stay with Elena Nappa at Borgo Argenina. Look her up on Facebook. She is in a great location just south of the Chianti region and you will have an enjoyable time when you get to cook with her and all of the guests in her huge kitchen !

Selita with Casa Selita B&B and Jeanette with Casa Chilenne B&B are also great options in Orvieto and Cortona if you would like to split your stay between different locations. We thoroughly enjoyed the homemade apple cake Jeannette made (when you arrive she greets you with a homemade dish and cappuccinos !! ) and hiking up to Orvieto through the olive orchards one night with our flashlights Selita supplied !

I would recommend you stay at the Agriturismo Casanova di peschille just south of San Giminagno. San G can be a real bear of a town between 10 ish to around 4 when the tour buses get in and get out. Experience it one day for fun then go back one evening for a delightful picturesque village From Casanova you are also just a short drive to Poggibonsi for the regular bus to Florence. That way you control how long you want to stay there. You sre also a short drive west to Volterra one of our favorite towns, then on to Lucca, not a favorite at all, then Pisa. See the tower and the duomo, buy a tee shirt from the market then get out. You will enjoy the Casanova, the pool, the views and a cooking class if you wish. As you can tell we love the area, that's why we're going back again next year. Good luck relax enjoy.

Everyone,
Thank you so much for all the help comments and suggestions! My mother and I have been compiling all of your suggestions and we are putting together a draft itinerary. Thank you so much!