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Tuscany area ides where to stay - how to plan itinerary

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We are looking for ideas for this middle part of our trip. We would like to stay in the country on days 9&10, possibly near Greve in Chianti or somewhere so we are close enough to drive to Florence one day and Lucca and Pisa the other day. We would like to stay in a family owned Agriturismo
or B&B to experience the country life for a couple days, maybe a home made dinner ()but not sure we have much time for that given the full days we want to explore these three cities. Any suggestions are welcome - thanks!

Drive from Sorrento to Orvieto 3 hrs 54 min (have lunch)
Drive to Montepeluciano (51 mins) Explore Montepeluciano and eat dinner
Day 7
Wine Tour?
Montalcino?
Assisi?
Day 8
1 day - Heart of Tuscany tour (3-4 hours) includes La Foce Garden tour, Siena, possible Brunello Winery tour?
- La Foce Gardens, (Make resv - Guided tour only, €10-50 min tours, 11:30 &15:00 (3pm) on Sat.)
- Visit Pienza, etc. – lunch?
- Stop for great photo ops of Cypress lined driveways, etc.
- Dinner??
Day 9
Drive to Greve in Chianti or San Gimignano for 2 nights. We are looking for an Agriturismo, B&B or similar type place to stay with homemade dinner or meals/family-run, etc. (Most of these that we have looked into do not have air conditioning, and that may not be what we want to stay in - but undecided right now.) We are visiting Pisa, Lucca and Florence from this place. Any suggestions or names or places to check out?
Visit Pisa and Lucca
Day 10
- Visit Florence for the day
Day 11
Drive from Greve in Chianti (or San Gimignano) to Monterosso in Cinque Terre(2hrs 18 min)
Day 12

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