I'm deciding between a 8 day and a 10 day Eurail pass, and the deciding factor I think will be how to get between Tuscan hill towns. Is there local train service from Siena out to the surrounding towns? Or would I need to use Eurail days?
It depends which hill towns. But you'll be 10 times as efficient by getting a rental car.
A Eurail pass does not make sense for Italy. Italian trains are cheap.
Siena has poor train connections. Much better by bus.
As I remember, there are not a lot of the hill towns that are serviced by train. Bus is more likely.
Your rail pass will work between the larger cities, and a few of the hill top towns, but not the more quaint ones. Orvieto has a train station, but Pienza does not. San Gimignano/no train, Volterra/no train.
You will need to figure out the buses and take them, or plan on renting a car and picking it up in Siena for a few days.
Tricia - I guess the simple way to put it is that they are called "hill towns" for a reason. Trains do not like to go up steep inclines particulary to small villages. You can get close to some of them - but you'll have to utilize alternate transport from the nearest station - i.e. bus, taxi or rental car to get to the charming little hill towns. Have fun.
Take the advice above and do not buy the rail pass! You will not travel enough to justify the price. The trains are cheap in Italy and in Tuscany the bus service is good. Be brave, rent a car! You'll be able to see much more. Driving in the countryside is pretty easy.
If you're just in Italy, the pass isn't worth it for train travel in general. You still need reservations on the fast trains so you'll be visiting train stations anyway to use the kiosks or stand in line, and the cost is the same or more for the pass compared to pay-as-you-go.
As for hill towns, you can pick a few that can be visited from train stations at the foot of the hill town (Perugia, Orvieto, Cortona, etc). But its much quicker and more convenient by car.
I still feel lost, so let me clarify a little. We're doing a personal highlights of Europe in 22 days tour. We'll be coming into Italy from Paris, and on Rick Steves' recomendations, we're doing the Cinque Terrere. Then to Florence, Rome, and Venice. But I'd LIKE to stick a trip to Tuscany in there. Renting a car is not going to happen. Is there a good way to do a nice hill town tour in a day or 2 by public transit?
Between Florence and Rome, there are several hill towns that are easily accessible by train. Cortona is about 15 minutes by bus from the Camucia train station. Orvieto (in Umbria, but still a hill town)also has a train station. You should also be able to get buses to some of the towns from Florence. So you could either stay in Florence and take a day trip to one of the hill towns or you could stay overnight in Cortona or Orvieto between Florence and Rome. I think the best thing to do is get a Rick Steves Italy book and perhaps a Lonely Planet Italy book and look at some of the transportation connections for the hill towns and also which ones appeal to you. I don't think you will want to use your Eurail for these days. Even if you take the train from Florence to Cortona, it is not very expensive.
I've been to a number of the Hill Towns and this year I wanted to spend a couple of nights in one that I had not been to. I could only use public transportation, so I chose Cortona.
Went to Orvieto in July--what a beautiful place. It would be very easy to do. As others have said, the train goes to the base of the "hill" town. You then take the funicular up. Orvieto is very quaint, has a beautiful cathedral, great restaurants and lots of charm. The train from there to Rome is 1 hour. Have a great time!
I would say, pick a hill town that is a bus ride from a train station and spend the night. Arrive in the late afternoon and watch the tour buses leave. Depart midmorning the next day.
San Gimignano might be one such, it can be pretty touristy in season but less so at night.
You might be able to cover two towns this way, I don't know, but without a car a "tour" seems pretty hard.