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3 nights in Tuscany, please help!

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i no I dont have much time but am looking for a place to stay with my boyfriend who i have not seen in 7 months! so i will be coming (driving from santa margherita) and looking for a great place that has charm, romance, and a town to dine in at night that would be somewhat close to the hotel,winery that i would be staying in.. after the third night i will be driving to rome for the last leg of my trip! any suggestions would be greatly appreciated as i am going in 20 days!! looking for price between 200-300 a night us dollar and a pool would be great!

also are the winerys in prodoction in the summers?

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