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Tuscany or Umbria for 2 weeks in November

I have been to Italy several times (Tuscany and Umbria and elsewhere) I am having difficulty trying to decide where to stay. Looking for suggestions of apartments or B&Bs for 2 weeks in early November I am looking to stay put and just enjoy the area with maybe 1 or 2 train day or 2 day trips. Looking for a place that has WiFi in the apartment or the B&B. Would like to hear your experiences in November I prefer "in centro" in the city, as I do not wish to rent a car. Looking at Lucca, Pistole, Orvieto, Prato, Arrezzo, Cortona, etc. Purpose of the trip is to practice and improve my language skills. Thanks in advance for any suggestions.

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