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Planning a Trip to Italy in September

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My husband and I are planning a three week trip to Italy in September. I was there years ago and he has not been. We are planning mostly on training but maybe a rental car in Sicily? Before we get too far in our planning, we would like input. We want to focus on the South but maybe a quick trip North. We will be flying in and out of Rome. Rougth plan is 2 nights Rome, 2 nights venice, 2 nights florence, then train down to naples (because Pompeii is a must for me), down to cosenza and then on to sicily. Note there are no time estimates for the south as we need suggestions. Cosenza is a must because my mom is from there (no relatives or anything, just want to see it) and sicily is a must for my husband. Maybe one night naples, two nights Cosenza and then on to Sicilily?

Any must dos? Anything that won't work? car on Sicilily?
Somewhere I would like to stay at a monestary or convent if anyone has suggestions.
Thanks.

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