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Wine Tours from Siena to Montepulciano

Has anyone taken a day long, small wine tour group that will visit at least two wineries heading to Montepulciano from Siena? We aren't interested in a tour with a busload of people or a private tour. We will be going in late September of 2025. Did you have a positive or negative experience with the tour operator?

Posted by
156 posts

From Montalcino, we did a private day tour wine tasting in October 2024 with Fabrizio at Ciao Fabry Tours. It was a private trip but was pretty reasonable cost. He picked us up in Montalcino and took us to two Brunello wineries and a sheep farm near Pienza for lunch - all three spots were fantastic. He customizes tours so you can probably work with him to get the itinerary you are looking for. He also does cooking classes in Montepulciano. Super knowledgeable and fun, we had a great time.

https://www.ciaofabrytours.com

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132 posts

In October 2023 we went on an all-day small group wine tour with Tuscan Escapes. It was fabulous. They picked us up in Siena and we drove through the beautiful Tuscan countryside stopping in a small medieval village for a morning coffee and then on to Pienza, where we explored this gem on our own. Then we had a farm to table lunch on an organic farm, with their wine. Our last stop was wine tasting in Montepulciano before returning to Siena. Our guide/driver was great, filling us in on the history of the area as we travelled along.