There are nine of us that will be in a villa outside Florence from October 8 - 15, 2016. We plan to take the train into Florence a few days. On other days, we have cars and plan to drive to a few of the Tuscan towns (Siena, Greve, Lucca, San Gimignano). For some towns we make take the train or bus and leave the cars at the Villa. All of us will have Rick Steves' guidebooks and most will have downloaded the app with walking tours. The app has general descriptions of the towns, but not the walking tours that you find for Florence, Rome, etc.
Should we have a guide when we get to town?
Are the towns small enough where we can merely walk around, see the churches, wine shops and the like without a guide?
If your answer is "Yes" for certain towns and "No" for others, please share your thoughts.
I am trying to organize four couples and a single to make sure we have the best time that we can have. There is a balance between too much organization/structure and too much free time. Any suggestions will be greatly appreciated.
Thanks!