I've never encountered a single supplement, but I always stay in pension-type places and not in large hotels. Consult guide books like Frommers, etc., for room recommendations. Some will disagree, but I always prefer booking my rooms before I go, re fax. I was very thankful that I did that on my May trip, because places seemed to be booked solid.

It's really easy to get around on your own. Train service is very good. I spent a day in Rome, staying in the vicinity of the station, then hopped a morning train to Florence. (For me, the rail pass worked well and saved a lot of time standing in line). From Florence, it's a cinch to catch buses to areas in Tuscany you'd like to see. Siena, San Gimignano, and Lucca are all easy--and fabulous--destinations for day trips. I found it much harder to get out to the Chianti region from Florence. Those hill towns are more accessible from Siena, if I remember correctly. And do not--repeat, do not--miss Venice! It's sensational!

In Italy, I've found people to be very patient, kind, and helpful re solo travelers. In restaurants, wait people always seemed to go out of their way to make me feel comfortable when dining alone.

Hope you have a wonderful time!

Didi