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Help with Tuscany for a week late May/early June

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Hi all,


I am helping a friend plan a trip for herself and her husband - both in their late 70's - active and sharp people.

They have never been to the Chianti area or the Val D'Orcia region and are hoping to do both areas - and here's the kicker - without a car as they don't want the hassle of driving. They are willing to hire a private driver for some days (may end up being most days...we will see).

Thinking 4 nights in Chianti and 2 or 3 Val D'Orcia.

So, my questions are as follows:

1. Where to stay in these areas - looking at Greve/Panzano, Castellina for Chianti area and Montalcino, Montepulciano or Pienza for Val D'Orcia. . If anyone can recommend upscale hotels with a pool, on site restaurant and (not sure that this exists) an onsite driver to do short trips into the closest town, that would be terrific. They will probably be best staying close to, if not in town, in these places. For Pienza, was looking at Il Chiostro di Pienza which looks like an option.

2. Private drivers - does anyone have any suggestions in this regard? I know of Luca from Hills and Roads.

3. Cooking classes and nice wineries with lunch restaurant on site - any suggestions regarding these are so welcome! I am compiling a nice list.

Thanks

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