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Southern Tuscany - 1 week itinerary - need some help!

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We're leaving for southern tuscany for a one week stay near Pienza (starting on a saturday) in a few weeks and could really use some help with our itinerary planning.

We love to eat good local food, soak up the local culture, visit small tuscan hillside towns, drive around to see the beautiful scenery in tuscany. We don't want to be "rushed" but do want to see the highlights of this part of tuscany.

I stayed for 2 weeks in the Dordogne last year and absolutely loved it so I'm really hoping southern tuscany would offer the same magical experience.

Usually I have more time to do my travel research but work has been unexpectedly busy the last couple of months so I could really use some help from fellow fodorites!

What we have scheduled in the agenda so far

1. Monday - Avignoensi Estate - noon winery tour + lunch

2. Tuesday - half day cooking class with Ecco de Cucina near Siena; most likely we will visit Siena on the same day after class

3. Wed - La Foce garden visit in the late afternoon. I emailed them for a reservation but apparently they don't take them and just asked us to show up.

The above is all we have planned and I could really use some help with the area we should cover (something that is really hard to get from a guidebook - I am using the trusted green michelin guide on tuscany.)

My other questions are:

1. Given we are spending a week in this part of Tuscany, is Chianti / San Gimignano do-able as a day trip or will it be too hectic? What about the Arezzo / Cortona?

2. I love driving - any drives that are the highlights of your trip in this part of tuscany?

3. What are some of your favorite restaurants near or in PIenza? We are staying just outside of PIenza so we would prefer to eat either near or in Pienza to avoid a long drive home.

4. I would love to hear some of your favorite moments/highlights in tuscany!

Thanks in advance for everyone's help.

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