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Based in Cortona 5 days -- Ideas for Activities and Daytrips?

Wife and I will be at Villa Di Piazzano just outside Cortona for 5 days in late October. Would be grateful for recommendations -- based on others' experiences -- for activities and day trips around Cortona or within about an hour drive. We'll have a rental car. We like walking. We're eyeing Perugia, Assissi, and Montepluciano. Would also be open to stopping in smaller towns or scenic places for a few hours along the way. Maybe along Lake Trasimeno? Also interested in tastings/tours for wine, olive oil, cheese, and farms; have seen recommendations for a few of those within about 30 minutes of Cortona. Thanks!

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