I just flew to Venice (by myself last May) and asked Italians in a bike
shop for the best route to Rome. From Rome I headed up to Tuscany and
then to the Lakes in the North and back to Venice. It took me 3 weeks and
about $3k. I learned that you should positively enter and leave large
cities like Florence, Venice, Rome etc. using the trains to avoid the
traffic (they're so easy and cheap.) And next time I would go south from
Tuscany because the winds would be at your back. The winds were extremely
strong.

It's easy to find nice hotels or Agritourismo (farmhouses) for $30-40.
Then ask for the best restaurant in town, a glass of the local wine...

I had a terrific time. I had nothing planned and it all worked out.

I liked San Gimingnano (just south of Florence) the best.


Let me know if you have any specific questions.

-Gary