Help with Itinerary - first trip to Italy

Cindy, My suggestions are similar to those that Rob mentioned. With such a short trip, using trains would be a more efficient use of your time. From Florence to Siena, using the Bus is a better option, as passengers are dropped right in the centre of town rather than the bottom of the hill where the rail station is located. The travel time between Bus and Train is not much different. There are a few "issues" with driving in Italy. Each driver will require the compulsory International Driver's Permit, which must be used in conjunction with your home D.L. Failure to produce an IDP if requested can result in fines on the spot! Especially in Florence you'll have to contend with Zona Traffico Limitato areas, with each pass through one of the automated Cameras resulting in a €100+ ticket. This is a brief summary of the issues. I can post my usual "boilerplate" text on this subject if you're interested. You could also have a look at some of the Threads here on HelpLine regarding those who have received violation notices from Italy. One method you could use would be to limit your stay to Venice and Florence. While in Florence, you could make day trips to Siena and Lucca. That would minimize changing locations, which generally uses about half a day each time. Happy travels!

I'd take the train from Venice to Florence simply to save the hassle of a long drive and a one-way rental. In Florence you have options depending on where you decide to go. If you decide on Siena you could take the train or bus to there. I would not drive because you will not be able to park close to the historic old part of the city anyway. If you decide on a smaller hill town (e.g. San Gimignano) you could either rent a car in Florence or take a bus. San Gimignano is also quite close to Siena and is an easy day trip by bus or car from there. I like Siena as a base of operations. If you based there, you could spend one or two days seeing the sites there and day trip out of the city for one or two days. The area around Il Campo is very nice for eating and hanging out at night in Siena when you return from your day trips. If you do decide to rent a car, I suggest that you make a reservation in advance to ensure availability. Good luck.

A car is not of any use in Venice and more of a liability in Florence too with the ZTLs. Take the train Venice->Florence then take a bus to Siena or train to Lucca. That's what we are doing in a few weeks. The only area where a car would be good is the Tuscan countryside. We are having a driver take us to several towns in Tuscany for a day, we could rent a car, but we will have a driver who knows the region and knows where the good sites are. We will probably visit Chianti, San Gimignano, Volterra on that day as we are staying in Siena after Florence.

How much does it cost to hire a driver for the day in Tuscany?

You can take the train to Florence and after seeing what you want in the city go to the airport and pick up your car and head out to the Tuscan countryside. You can get directly on the freeway without going into the city. I have driven this area numerous times and found signage to be good. One problem area for me has been Sienna...difficult to find my way around. I always stay in one of the smaller surrounding villages...whatever I feel like at the time. One of my favorites is just outside San. Gim. a tiny hilltop village called San Donato...not much there except a vineyard, a church and the beautiful Tuscan view. Anywhere in that area is amazing. I love just driving around and stopping whenever I want, either for a picnic, to take photos, or stop at a winery or restaurant along the way. Have fun!