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4.5 Days in Tuscany

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Hi All!

My husband and I will be in Tuscany from September 27th-Oct 2nd (5 nights and 4.5 days) and will be staying in Montepulciano @ Salcheto Winehouse and will be coming from Montefalco in Umbria. Our main priorities are food, wine and views. I don't need to plan out every detail of the day but I'd like to have an idea of what we want do in general every day., especially because we want to visit wineries. We will have our car (don't worry, I know not to drink a lot and drive :) ).

Can you please help me decide how to piece the days together? My husband wants to fully plan a day on his own as a surprise so I have 3.5 to decide on. I want to visit Cortona (I am thinking on the way to Montepulciano), Chianti, Montalcino/Pienza/Montepulciano, Chiusi, San Antimo Montasary.

My questions:
1. How to best piece this together?
2. Should we visit Cortona on the way to Montepulciano or do it another day? Which other towns could we pair with this?
3. How would you do a day in Chianti?
4. Do i need to make reservations at all the wineries or do a lot of them just do walk in? I'd really prefer not having to stick to a schedule.
5. What else do you suggest we do?
6. Any recommendations for vineyards/agriturisimo to have lunch with a view?

Thanks in advance!

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