My husband and I are planning a trip to Tuscany this May and would appreciate suggestions on which towns would be best to base ourselves. We have 8 nights and thought we would stay in 3 different places to eliminate driving and to be able to experience various places. It is a first trip for us both and hope to see the "highlights" as well as definitely time spent in Montalcino as my husband is a lover of Brunello wine. We are not planning any time in Florence or Pisa as we've been there already. Would you recommend staying in Montalcino? We would appreciate any tips and would also like to know if it's best to fly into Florence or Pisa (we are American expats living in London in our 30s) Thanks so much in advance!!

We really enjoyed basing ourselves in Siena (actually just outside the walls) at a great place with free parking and near bus service into the Centro of Siena (5 minute ride) Frances Lodge (www.franceslodge.it). It was about 30 minutes to Montalcino, 60 to Cortona, 45 to Montalpulciano, 45 to San Gimingano. We also spent a day driving through Chianti as well. We liked sleeping in Siena because it seemed to have more to offer at night by way of restaurants and stores being open later.

Stefanie, try to find my trip report from last Oct. at slowtrav.com I agree that at least 2 locations is good with 8 days. In my mind, Montalcino is one.
So, what about the other. If you hope to include Cortona and Chianti look at a really cute B&B in a fabulous location at www.borgoargenina.it The owner, Elena, has done a masterful job of creating a boutique B&B on a hill top in Chianti. Flying to Florence would be better. Have fun, and do not miss input about Tuscany at slowtrav.

Thanks swalter518!!! Sounds like a great option.

Thanks to you too, bobthenavigator and i will definitely check out your trip report.