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Tuscany with Grandma - final planning phase

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I need my fodors friends to help fill in some details, please. My DG has decided to join me in Italy for about 10 days at the end of February. I know I was thinking Naples/Rome thanks to all your helpful tips, but I don’t think that’s a good fit for her, so we’re doing Tuscany.

The plan is 4 nights in Cortona with day trip to Arezzo, 2 nights in Assisi (with visits to Corciano, Ermeo delle Carceri and Monte Subasio on our way in and Deruta, Todi, Orvieto on our way out), 4 nights at an agroturismo near Montalcino/Pienza (trips to lots of tiny villages and some monasteries in the area)

Questions:
Where would you suggest going to mass in Cortona?
What are some of the most interesting vineyards/wineries to visit?
Any guided wine tours you’d suggest?
What agroturismos have you loved?
Any other helpful tips you guys have?

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