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Italy Timing

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My wife and I are in the early stages of planning a 3 week trip to Italy for 2013. Our tentative destinations (in no particular order) are:

Venice
Rome
CT
Tuscany
Amalfi

We can either go the first 3 weeks of May or the three weeks following October 15 (last 2 weeks of October and first week of November). After reviewing wunderground, it seems like the weather might be ever so slightly better in May, but that it doesn't really make that big of a difference.

If we go in May we we probably work south to north and if we go in November we will probably work north to south.

Thought I would see if anyone on the board had a compelling reason why one would be better than the other.

Thanks

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