Hello all!

I am planning a wine tour and countryside lunch for a large group - possibly as many as 25 people. Our group will be based in Siena. We would like to visit a winery or two and have lunch in the countryside. We are looking for a beautiful day in the Tuscan countryside with great views and delicious food and wine. We would like to spend the day in the Chianti area or around Montalcino. We are not interested in visiting a city on this tour. We will definitely want transportation, but not in a large bus. So maybe 3 vans traveling together. We have visited Tuscany several times before, and are happy to make our own bookings. We are also open to having the day organized for us by a tour guide. I am looking for suggestions for wineries that accommodate large groups but ideally are not too corporate and restaurants that can accommodate our group outdoors, ideally with a view and good food and wine. Any suggestions for transportation providers are welcome, as well!

Thanks in advance for your collective wisdom!

A countryside restaurant that can serve 25 people simultaneously... outdoors... with a view... It would probably need to be a set menu that might not be terribly imaginative.

A winery that does large group tours but isn't "too corporate." I'm not sure how you define that. Small, charming wineries usually limit group numbers and not all have dining facilities.

For 25 people, I think you would need 4 vans, even if members of the group would be the drivers. For me, moving a group that large in multiple vehicles would nix Montalcino. I'd stick to Chianti and use a wine tour company to figure out the logistics.

FYI, there are wineries in castles, former monasteries, fortresses, borgi, etc. Some have been operated by the same family for generations, and others are relatively "new." Some are all organic. Some offer tours of their gardens, art collections, castle interiors, cooking classes, olive oil tasting, etc. Some larger wineries have restaurants serving lunch and dinner, and some offer picnics on the grounds. Tour/tasting prices are very wide-ranging, and I expect guided tour rates that include transportation would be likewise wide-ranging. Before you investigate the many options and/or talk with a tour company, you'll want to have some parameters decided... how much drive time, cost per person, what sort of atmosphere, how many wines to taste, lunch at the winery or drive to another place...

Just one very quick comment because Jean seems to have covered most the bases (other than to say what you are seeking might be a unicorn -- not corporate but 25 people wouldn't overwhelm, and 'local/character' restaurant with seating for 25 outdoors)

For a group that size -- even though it isn't what you'd prefer -- one large coach would be much easier/more practical than 4 mini vans for sure.

Funny... I was going to use the word "unicorn."

I do think you can find a winery or some combo of venues that will work for your group, but I wouldn't DIY. I'd communicate with a tour company or two.

Thank you, Jean. I did find a tour group that can help me organize this. They have been wonderful! I am not usually a group traveler, and thought this might be a heavy lift. But it will be wonderful if it works out. Thank you for the suggestions!

Thank you, Janis. Yes, a needle in a haystack! I don't usually travel in a large group, but had to give this a try because i want to share this beautiful place with our guests. Many thanks!