Untitled by Anabaena
Great place, spent two months biking through Tuscany down to Sicily last fall. My favorite places were Bologna, Siena, and Catania. One thing I did not consider before I went, which I wish I would have, is that after mid-October a lot of things close down outside the major cities. I would recommend keeping clear of beach towns after mid-October because many restaurants and hotels are closed.
Other things to keep in mind: Outside major cities most restaurants are closed from about 3pm to 7pm daily. Look into agritourism options outside major cities. I did WWOOFing for a few weeks and worked on a farm in exchange for food and a place to sleep. Great way to experience the culture and save money.
If you’re interested in biking through Italy I would highly recommend it. It was definitely hard—a lot of sleeping on the side of the road, sore legs, and being lost. But, it lets you see the real Italy, places where people are still interested in where you’re from and what you’re doing there. The Italians are really bike-friendly and were very enthusiastic (sometimes too much) about helping. Lonely Planet has a cycling Italy guide that’s complete garbage, don’t bother with it. Get yourself a good bike map, bike mechanic book, and regular guidebook and you’ll be just fine.