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Help with Italy itinerary (18 days: Rome, Umbria, Puglia, Amalfi?)

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We just booked tickets into Rome and out of Naples at the very end of August (most of travel will be in September). My husband and I have been before (our travelogue: http://www.hitherandthither.net/2005/06/travelogue-italy-june-2005.html), but this time we will have a 3 yr old and 6 mo old along. We're avid travelers and have done a lot with one child, but obviously we'll be going slower this time. The goal is to enjoy good food, culture, and some beaches (but not so much the historical sights/museums).

Could use help with itinerary and especially transportation advice. I'm concerned the transportation logistics will make this too ambitious... but would love help! Hoping to move around more at start and then end with relaxing week of staying put at beach.

Thinking perhaps:
August 23-24 arrive Rome
24, 25, 26 (3 nights) Rome

August 27 Car north to Umbria / Tuscany
27,28,29,30 (4 nights) Hill towns in tuscany area (day trips from either agriturismo or base ourselves somewhere like Siena with a couple of day trips?) (is 4 nights enough? or should it be 5 and we split time between bigger town and villa?)

August 31 or 1st Drive south to Puglia
31, 1, 2, 3 (4 nights) Puglia (possible stops: Matera, Matarea, Lecce, Otranto, Polignano a mare, Monopoli, Locorotondo, Alberobello) Thinking Matera plus one shore base like Polignano?

September 4 (7 nights) Drive to Positano and settle into apartment for week. (But should we cut it to 6 nights? And if yes, to which part would we add extra night?)

September 11 Head to Naples airport and fly out in afternoon.

Thoughts? I haven't actually researched the driving/transportaion yet...

Thank you in advance!
Ashley

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