Has anyone ever walked from town to town in the hills of Tuscany without a guide or tour company? I'm trying to figure out how to get my luggage at my destination
Just my IMHO but if you're planning a point-to-point hiking trip, I wouldn't take more than a backpack that you'd carry yourself. Otherwise, you'd probably need to book a "walking holiday" package which provides baggage transfer like these:
http://combadi.com/276-tuscany-walking-holiday-active.html
http://innwalking.com/product.aspx?id=1546&lang=1&mid=-1
I have not used these services nor am recommending them; just using them as an example. You might be able to pay a cab service to deliver your luggage as long as you know exactly where you'll be ending up.
I have not but while researching around Lake Maggiore I came across a Cicerone guidebook for walking between towns. I ordered it and it's quite interesting. I'm going to try 2 of their walk/hikes around lake towns this september. The company has a lot of other area's for walking. Here is their book for Tuscany. Being a UK company i'm not sure if you'll find it at your local library here in the states. Mine took about 10 days to arrive in the US when I ordered it online.
http://www.cicerone.co.uk/product/detail.cfm/book/489/title/walking-in-tuscany#.VrjJ-PkrJhE