Wine Tasting help needed!

I would take a tour and leave the driving to someone else. Don't you want to be free to taste as much as you can?

have a designated driver maybe? When I did my wine tour back in April I only had sips and maybe a total of 2 small glasses over the course of I think 3 hrs with a luncheon. Btw I also stayed in Assisi and can recommend a beautiful place. I loved it so much I am going back there end of August. Here is a link http://www.castellopetrata.com/hotel-assisi-near-basilica and here is a link to the near by winery that was so awesome . https://www.avignonesi.it/en

If you are able to get an early start on Day 1 (7-9 am for example), I would visit San Gimignano and Volterra as a daytrip and then drive to Montepulciano and check in to my hotel/agriturismo. (Volterra is about 1-3/4 hour drive to Montepulciano.) I would use it as home base for:
Day 2: Assisi (the drive to Assisi from Montepulciano is only 1.5 hrs.
Day 3: Orvieto and Civita di Bagnoregio (the drive to Orvieto from Montepulciano is only 1 hour)
Day 4 and 5: Using two days to see the Val d'Orcia area.

Day 6: Drive to Siena.

This plan allows for a nice 5-night stay with the same lodging, you get to know the people who own the place, and that is part of the charm, too. It also eliminates a lot of packing, moving, checking in/checking out time that can be devoted to visiting villages, tasting wine, etc.

Hire a driver for a half-day when you are in the Val d'Orcia area to take you to several wineries. Be sure to make your winery visit reservations in advance. There's a great guy by the name of Angelo who provides driving services in his van (+39 340 9586833). He speaks English well enough and is very dependable and kind.

all of these ideas sound great, thank you so much!!

Does anyone have a recommendation for a day good wine trip that we could take? I'd hate for someone in our group to miss out because they have to be the driver.

Also, we are both pretty well versed in how wines are prepared and processed so we'd really like to save time by booking guided tastings instead of the whole guided experience (walking the vineyard, bottling, etc). It looks like most wine tasting tours take 3+ hours because they include these steps. Is it possible to do tastings without the actual tour anywhere?

Thanks again!

If you have the time, I'd highly recommend doing a lunch w/ wine tasting. Many of the vineyards offer this without a tour. Two we've done are:
Fattoria dei Barbi in Montalcino
Avignonesi near Montepulciano

Wonderful food paired with the vineyards wonderful wines

Larry the Avignonesi near Montepulciano luncheon I had also recommended above. Wasn't it just outstanding? Im still dreaming about it and I already made another appointment to be there in August with my husband. Just stunningly beautiful.