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2 Weeks in Italy in early October, part due

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Since you all were so helpful the first time around, I thought I'd post another few questions...we've nailed down our itinerary: Milan (1 night), Venice (3 nights), Florence (3 nights), Sorrento (4 nights) and Rome (3 nights) - please, no criticism on the scant time for each city...this is what we had to work with.

We'll be traveling primarily by train, utilizing buses, as necessary. Sorrento received 4 nights because we want to do Positano and the Amalfi Coast, Pompeii and Capri. According to a B&B in Sorrento, the ferries will be running to Capri and Naples when we are there in mid-October. No ferry to Positano from Sorrento, so I'm hoping we'll be able to take a local bus and get on and off. Will this be doable? Should we spend one night on Capri (Aiano Bed and Breakfast looks lovely)? Or just take a day trip from Sorrento?

Has anyone done a Tuscany/Wine tour with Alessandro Cammilli (he's extremely highly rated with Trip Advisor)? Alternatively, has anyone taken the Best of Tuscany Tour with Walkabout Florence?

Any other advice would be much appreciated.

Grazie!

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