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ITALY -Need help with itinerary - # of days in each city

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I'm a mature woman, traveling alone planing my trip to Italy around a 3-weeks working on a vineyard (Gotta give me props for that at 55+!)

I'm planned out the itinerary below to sandwich these 3-weeks hard work at the vineyard with stays in a number of cities. I have no idea if i've allotted too much time in any one place, or if I'm including too many towns + cities.

Could really use the benefit of an experienced traveller of Italy insights and input about this schedule:

NYC-Venice - Sept 1
Venice - Sept 1- 6
- Allowing day for jet lag, Sep 2nd is annual Regatta + the Film Festival is that week)

Florence - Sept 6-9
- it's on my way to Vineyard - no lag + only short train - 1 less day?)

Siena - Sept 9-30 (3-wks vineyard in Siena reg)
- Have weekends off - Planning day + overnight trips to Siena + other towns in Tuscany

Rome - Sept 30- Oct 6
-Could 6-nights possibly bee too much? So much to see!

Amalfi - Oct 6-11
- Is a week too long or is Amalfi? Or is it good home-base for bus to other towns?

Naple - Oct 11- 15
- Flying out of +exhausting to travel from Amalfi and get on international flight same - Is 5 Days in Naples too much?

SHOULD I CUT SOME STOPS, CONSOLIDATE STAY, SPREAD OUT? DOES THE ORDER MAKE SENSE. Surprise it's sill in mid 70's in Oct - though is would be cooler...is that a factor to consider?

As always, thanks for you help

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