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Italy with older mom

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Traveling with my 70 yr.old mom to Italy in early July.( She is very active.We just went on a nyc trip in April and she was fine as far as walking) I plan to go to Siena for a few days but other than that, I would like to take my mom to places that are safe. She tends to worry too much so I would like to stay away from places where there are lots of pickpocketers/thieves. I last went to Florence 5 years ago so can't remember if it isgenerally safe? We would be taking the train from Milan to Tuscany. Will we be safe from thieves on the trains? Any suggestions for safe cities to visit in Tuscany? Day trips from Siena such as wineries? Is air-conditioning a must for hotels due to the heat?

Thanks!

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