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Should we stay in Florence or hillside towns in Tuscany?

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I need some help. My husband and I are traveling to Italy for the first time in the end of Sept. We are flying into Rome for 5 nights, then CT for 2 nights, Florence/Tuscany 5 nights and lastly Venice for 2 nights. My big question is whether to stay in Florence for all 5 nights or find one/two hillside towns to stay in. The reason we are thinking about Florence for the entire 5 nights is we have hotel points for the Westin and we are trying to avoid moving hotels too much. BUT my concern is we would enjoy the experience more in the countryside. We are 30yrs old and love food, wine. Not as crazy about the museums and art right now. Would love to do winery tours and maybe cooking classes. My question is do you get the same experience day tripping by bus or train from Florence to San Gimigano, Siena, Montepulciano, etc? Thank you in advance for your help and advice!

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