Buongiorno,
As a lone female traveller - I try not to let anything stop me from truly enjoying my surroundings and to be honest, Tuscany is a dream place to travel, even if on your own. Of course, follow some simple safety precautions but you should fee safe pretty much where ever you go.
There are many activities October that are excellent opportunities check out these two calendars:
http://www.visitflorence.com/florenc...-florence.html
http://www.discovertuscany.com/tusca...n-tuscany.html
*definitely check back on the calendars closer to your arrival because the exhibitions and shows change every year!!
Last year the organization That's Prato had some great tours (free! and in English) very friendly groups and there are also many hiking groups you could hook up with for a day, minimum cost (15€ or less) and many times they will help you organize transport (check out Sentieri in Toscana or Hike&Smile on FB)
Have Fun!!
Donna Denise
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