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June/July or Sept/Oct - Italy with the kids

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Happy New Year everyone!

I am planning a trip to Italy with hubby and the kids (ages 15 and 12 - great travellers), from Australia for three weeks. Our options are the June/July school holidays which start at the end of June and which last for three weeks, or the Sept/Oct holidays which start at the end of September but which only last two weeks. We would need to take the kids out of school for a week which I don't really have a problem with for the younger child but I am more reluctant for the older one. Our itinerary is yet to be confirmed but I am thinking three nights in Venice, two nights in Florence, three nights in the Chianti region followed by a week in a villa or agriturismo in the Val D'Orcia region. We would then end in Rome for five nights.

The pros and cons that I see for each are:
- hotter and possibly busier in June/July (but we do live in Brisbane where it was over 40 degrees C today so we are used to the heat)
- longer days in June/July
- cooler and maybe quieter in September but it is another three months to wait!!!
- having to take a senior student out of school in the final term of the year (we run Jan to Dec in Australia)

Given our possible itinerary what are your thoughts on each? I would also be interested in hearing about out of the way places to visit where we can avoid the crowds. We all enjoy just following our noses to see what we can see and won't necessarily be doing the usual tourist stuff. Is getting into the hills of Southern Tuscany a way to avoid crowds?

Thanks for any advice!

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