2 days in tuscany need winery advice
 

We will be staying outside Siena in a B & B for 2 nights. We'll have a car and would like to explore the region and visit and tour some wineries. First day we will be going from Florence to Siena. 2nd day Siena to Orvieto. Any recomendations for wineries, hill towns to visit, or other attractions?

OK I'm confused. You've lost a day.

If you are in Siena for 2 nights you have:

The day you arrive from Florence

A full day there (or in some wineries)

The day you leave (Orvieto)

When are you planning on touring Siena - the center day? Are you looking for just one winery on each of the other days. (And be aware that wine tasting is tasting - not drinking - since the legal blood alcohol level in Italy is lower than in the US - no more than 1 glass - at most).

And when are you going?

We are staying 2 nights in a B&B in San Rocca A Pilli (south of Siena). The first day we want to explore from Florence to Siena. The 2nd day we want to explore south of Sienna to Orvieto returning to San Rocca A Pilli that night. Day 3 we will drive to Rome and drop the car off there.

We wanted to take a tour and maybe have lunch at a winery. I thought we would need reservations for that. Can you recommend any special vineyards?

We will be there the 2nd week in Oct.

Does the first day include visiting Siena? On day 2, Siena to Orvieto and back is a lot of ground to cover in a day.

We have visited Ciacci Piccolomini several times. They offer a tour and a tasting. I can't remember if it cost anything, because my husband always organizes it. You do have to set ut up in advance. They don't have lunch, but if you keep driving south to Sant'angelo In Colle there are a couple very nice restaurants that serve lunch (I think they are closed on different days, so one should be open). If you do this you could combine it with a visit to Sant'Antimo and Montalcino.

If you aren't as slow moving as we are whenever we are there, you might be able to add on Pienza and Montepulciano.

I forgot to add... this year we might try this place (which has a lunch option):
http://www.avignonesi.it/en/hospitality#winetours

We haven't done it, so I can't report on it.