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Traving for 3 months with a child

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My son is currently 4 1/2, and I am hoping to go to Italy for 3 months when he is around 7 or 8 ( I am open to suggestions on this). I have never been, and I do not think I will be there before this trip.We are from the US and I am picking Italy only because it seems beautiful, relaxed and warm. I am picking this age because I want him old enough to appreciate it, but young enough to pick up the language and culture change easily. I want him to have an experience he will never forget, hopefully pick up the language and have the time of our lives. I am in the very early stages, and would love some advice on how to go about this. From the bit of reading I have done, it doesn't appear that working will be an option (correct me if I am wrong), if not I would be willing to work as a nanny, shlep gelato, or use my business degree. I am looking to rent a place for a month and maybe try another city for another month? This is going to be done on a single-moms moderate budget. Open to all suggestions- optimum age of child at time of trip, locations, time of year, sites to help on this planning. Any advice would be appreciated immensely! Thank you in advance.

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