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Amalfi Coast... Early September or middle to late October?

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My husband and I are planning a trip to the Tuscan hill towns and the Amalfi coast. We will be traveling with friends who prefer escorted tours for a number of reasons. We are looking for a tour which goes to the above places and maybe 1 other. Gate 1 travel offers tours to the Amalfi Coast, Tuscany and Rome or Venice. The problem is all the dates from mid Sept to early Oct are booked.
We have the option of a trip which will put us in Sorrento around Sept 10th, or one which will get us there Oct.21st. I am worried that it may be rainy and too cool towards late October. Any suggestions on which date would be better, considering weather and crowds?

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