I would recommend you go to Amazon and buy yourselves a copy of "Walking & Eating in Tuscany & Umbria" by James Lasdun & Pia Davis, the updated 2005 edition. Published by Penguin, ISBN number: 0-14-100900-4. I honestly cannot rate this book highly enough and I write that as someone whose former home lay just yards off one of their recommend walks. I can only comment on the walks in southern Tuscany but we bought the book perhaps ten years after first exploring the same area on our own and their advice, comments, description brought already familiar hikes even more alive. Their restaurant/where to stay recommendations too are spot on if your taste is not for tourist trap places and you're interested in staying more "en famille" than in a four star hotel. They also detail not only public transport advice but taxi company numbers! Several great walks through the major wine growing districts of southern Tuscany are covered, including a fab one from Buonconvento to Montalcino (the last stretch is a killer!) and a nice walk from Pienza/ Montepulciano.

Late September is a good time for hiking as a lot of the trails in this part of the region are unshaded and it's currently very uncomfortable, if not impossibly hot, to walk between 11 & 3. In addition to the book, when you arrive, all the local books shops/newstands sell excellent hiking maps but, to be honest, the route directions in the book are so very accurate, you could easily enjoy days of hiking without one.

Dear Catie,

thank you very much for your advice. We are really about to buy this book as we have got some very good references as well. We used LP Walking in Italy, but they have just two walks described. They are nice, but in too crowded places:)

We hope the weather will be more pleasent than beginning of June, when was our last time in Tuscany. We had to walk early mornings and late afternoon, otherwise it was killing due to high temperatures.