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Your Experiences in Italy

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My DH and I were supposed to go to Italy in May or June, I booked through my points with BA but with a little luck all that can be changed. We have some dear friends who have never been. They work long hours in healthcare and can't leave until September soooo I am asking have you been in the month of September, what can we expect. Do you have a favorite place in Tuscany - we would take the train from Rome to Florence and then get a car. We are young Seniors, love food, wine and all the destinations that everyone holds dear but for first timers and someone who likely will not get to return, where would you take them. Thank you for you advice.

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