We (3 of us/one room) have 5 days between Venice and Rome. We're taking the train mostly. We'd like to see Florence-Siena-Chianti-Lucca-Pisa. Not too interested in churches or museums, except Academia in Florence. Should we stay in one place and day-trip? When and where would we need a car? Florence would be convenient, but would another city/town be a better experience?
Our first trip, and I'll admit we want to go too many places.

Do a search on Tuscany hotels here and read some of the many reports you will find. I recommend training to Florence, maybe spending one night there so you can see what you wish (I'll bet you end up touring a church or two ) then picking up a car and staying in a smaller place, like Montalcino or near Monteriggioni, from which you can explore the hilltowns to your hearts content. Get a good map at Borders or Barnes & Noble, but you will find that driving and touring Tuscany is easy and enchanting. Now, enjoy your research!

I suggest, rent a car when you leave Rome and drive to Tuscany - Siena, Chianti, Lucca, Pisa. Tour that area for few days (3-5) then drop a car when you arrive to Florence. Spend few days in Florence and take a train to Venice. We've done a similar trip like this. http://www.emcoinc.com/travel/html/Europe/Italyrpt.htm

Thanks for your responses. I've narrowed it down to 2 nights in Florence, then rent a car and spend 3 nights in Siena at Hotel Villa Piccola Siena (1 mi. outside old city walls). We'll day trip from there.

Sounds like an excellent plan. You will have a great time.