You want to visit hill towns in Tuscany?

Yes, we think. Looking for a nice town to visit between Florence and Rome.

Not many hill towns on the train line between Florence and Rome. You could train to Orvieto for a small hill town. You could bus to Siena (Sita bus from Florence, Sena bus to Rome) for a larger hill town.

With only 8 days for Venice/Florence/Rome, I don't see how you will have time to add a hill town.

The town that makes the most sense is Siena as you can do this as a day trip from Florence and won't have to worry about your luggage. Siena is on the train line but if you could be more flexible you'll find that it's easier to take the bus as the bus stop is just outside the old walls to Siena. The train is several miles from the old town and you'll have to depend on finding a taxi at the train station and then a taxi back to the station.

Orvieto is another town on the train line between Florence and Rome.

4 locations in 7 days is a bit much but it's your trip.

Siena is not a typical hill town. It's more like Florence than any of the hill towns. You could take a bus from Florence to visit one of the small towns in the area, but the best towns to visit are in the south of Tuscany - like Pienza, Montepulciano, or Montalcino. I believe that the train from Florence stops in Chiusi, which is not far from the 3 towns I just mentioned. Chiusi is a center of Etruscan ruins and worth a visit and an overnight stay.

instead of getting a bus to Siena from Florence, you could get the bus to San Gimignano which is much more of a hill town, though it does tend to get very full of tourists in the day-time [but then so does Siena, though being bigger it can accommodate them more easily].

but I echo the thought that in only 8 nights, you are going to be hard pushed to see more than Venice and Rome, with a brief stop in Florence.

Assuming that you are coming from the US, your trip will probably look like this:

Day 1 - arrive Venice fairly early. allow at least 2 hours to get through passport control, customs, and travel to Venice proper. spend day settling in, getting over jetlag, etc.

Day 2 - venice.

Day 3 - Venice

Day 4 - early train to Florence. Arrive lunchtime-ish.

Day 5 - Florence

Day 6 - early train to Rome. arrive lunchtime-ish

Day 7 - Rome

Day 8 - Rome

Day 9 - fly home.

see what i mean?

As mentioned, Siena is probably the best bet, because it's easy to get to -- express bus from Florence. You could then take the train from Siena to Rome.

I don't know if Siena fits your idea of a hill town. Still, a lot of people like it, and it would be a convenient stop.

>>>You could then take the train from Siena to Rome.<<<

Bus to Rome is better than the train. The bus is just as fast and the train requires changes. The bus doesn't.

http://www.sena.it/Home/78-1-en.html

IMHO, unless you have been to these cities before you are really giving short shrift to all of them. And adding a whole day to see a hill town - when you don't even know which one you want to see or why - makes little sense.

Have you listed the sights you want to see in each place? Will you have enough time to do so?

You said visit, not stay at, so that makes a difference to my answer.

With only 8 nights to share between The Big Three, I am guessing you plan only 2 in Florence. That means that you can, practically, only really stop somewhere for a visit on the day you travel to Rome from Florence. There aren't any good options on the route from Venice to Florence.

As others have said the easiest option is probably Siena, but it is not a classic hill town. Unless you want to go to Chiusi and take a bus to Montepulciano, or something, which sounds really stressed for a stopover trip, then I would suggest Orvieto.

If you are spending 3 nights in Florence, then there are many more options to take a day trip to some the other fine towns mentioned.

If you absolutely HAVE to stop in "an Italian hill town" and are traveling by train, then I would pick Orvieto. It really is a hill town and is much more compact than Siena. You can have nice views of the surrounding countryside from the walls, walk around to see the small streets, see the wonderful Duomo, do the underground tour if time. It's then not far to get another train into Rome Termini station. You can read my trip report for what we did in Orvieto. We loved it (we also loved Siena, but like others have said, it's more like Florence than Orvieto is).