A car is an expensive headache (~€40 a day). Getting in and out of a city is confusing, and most towns are closed to non-local vehicles. However, driving around the Tuscany countryside has its charm, if you don't easily get motion sickness, as the roads can be very curvy. Autostade is about 60c per 10Km. Superstade is free.
2008.12.30 Tuesday.Volterra is a tiny walled Etruscan city, perched high on a hill. Much colder than its neighbors. Cobble streets, medieval piazza, decorated for the holidays.
Almost treeless, almost no tourists.
A 1st century BC Roman amphitheater is just off the northern wall (fenced in).Free parking can be found right outside the wall.
Napoleon spent 10 months in 1814 just off a hill top at Portoferraio on the Island of Elba before he escaped. It's a short but steep walk from the port, which is lined with restaurants and boutiques. Unfortunately it was closed on Tuesday. Breezy, yet much warmer than the inland. With many sandy beaches and unspoiled green hills, it seems quite popular with the Italians, certainly a pleasant place for exile.
Portoferraio is a smooth 1-hour ferry ride from Piombino, whose downtown is a couple of Km's away, making this stop inconvenient without a car. Train and bus services are infrequent: twice daily by bus to Florence / Massa Marittima / Grosseto / Pisa; the main train station serves Pisa and Grosseto, but requires a 30-minute connecting local service. Parking is free just a few hundred meters off the maritime terminal which also serves ferries to Sardinia. Out of the two companies that go to Elba, I prefer Toremar to Moby Lines as the latter is too stuffy and dark inside, and also charged me a bunch of unknown fees. Both a little over €10.
2008.12.31 Wednesday.Siena
Once a major counter force of Florence, now a sprawling city with as big a population as 700 years ago.
Its historic center is very small, pitched on hill top, walkable from the train (1Km)/bus stations. Medieval, an independent republic in the 12th century. Pedestrian, winding alleys in the color of burnt Sienna, very picturesque. Everything evolves around Il Campo, where you can find city hall and the highest civic tower in Italy. The duomo is elegant and colorful, with ringed dome and zebra like ringed columns. The head of St. Catherine of Siena rests in the heavy San Domenico, a very short walk north of the valley. 
Abbey San GalganoThis picturesque Cistercian ruin set in a relatively isolated grassy hilltop. The nearby small chapel built around the rock into which St. Galgano's thrusted his sword in 1180, (did he know King Arthur?) has a couple of faded frescoes and a unique but crude dome with concentric circles.
About an hour drive (~30 Km) S.W. of Siena. Take highway towards Grosseto from Siena, turn right for Monticiano. Go pass the town, heading towards Florence for 2-3 Km, turn left for San Galgano. Ignore the sign of "parking for San Galgano" in Monticiano. I followed that, and walked 2Km muddy trail until hitting a river where the bridge was withdrawn. After wading through the water, you can imagin how surprised I was at seeing 20+ cars right on the other side of the abbey. A group of friendly Italians took a 4Km detour to give me a ride back to Monticiano. One might be able to take a bus (twice daily, line 59? or 77?) from Siena to Massa Marittima, which stops at nearby Palazzetto.
Lucca feels down to earth: locals actually inhabit the not-too-small historic center. Small enough to walk everywhere easily. Friendly tourism offices distribute free maps and info. 
A glass tube Xmas tree stood in the center of Piazza Anfiteatro (a Roman amphitheater with not much Roman trace left), with moving lights, drew a small crowd on this rainy afternoon. At close to midnight, citizens young and old turned up at Piazza Napoleone (previously busy with kids on ice ring), brought champagne and fireworks in the dissipating rain. A stage was set with a giant screen and loud speakers for the count down and music. No orchestrated fireworks show. Emptied champagne bottles are perfect to set individual shooting stars.Birthplace of Puccini, of course the holiday celebration involves opera arias. The city was celebrating his 180th birthday. Almost every evening a concert was held at 6pm at San Giovanni, the first cathedral of Lucca dated to 12th century, with faded frescoes and ornate ceiling. It no longer holds service, but offers a portal to the Roman Lucca under the floor.
The most impressive piece of Lucca is the well preserved rampart, to the credit of Napoleon's widow Marie Louise: massive, flat top, as wide as a highway, lined with trees. Duomo San Martino has a maze set on the entrance wall close to the tower just outside the door. Guinigi (the dominant family in the silk industry) Tower with fragrant trees on top.Paid parking around the wall, slightly off, free parking for 2 hrs. Train station is just south of the wall, easy and frequent connection to Pisa.
