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Northern Italy Planner's Block -- Help!

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I have a dilemma. Because of some arrangements made last year, my wife and will find ourselves in Italy for sixteen days in early Spring, arriving and leaving through the Venice airport. Obviously, this is not a terrible dilemma. We had been looking forward to this return visit to Italy for some time. However, we have as yet made no other arrangements for our stay, and I keep "blocking" when trying to do so. We have previously enjoyed wonderful visits to Venice, Florence, Tuscany (Chianti region) and Rome. There are so many places we would still like see, some new to us, some not, but I'm unsure, both time-wise and physically how much we will be able to do. Of course, we want to "see it all!"

A very rough itinerary has come together so far. To limit the number of lodging arrangements needed, as well as packing and unpacking, I picture three nights in the Milan area, four in the Lucca area, six in S. Tuscany/W. Umbria, and two nights in Venice:

Day 1 Arrive in Venice -- Train to Milan area
Day 2 Milan area
Day 3 Milan area -- Lake Como and/or Lake Maggiore, Lugano
Day 4 Train to Lucca area -- Pavia stop off?
Day 5 Lucca area -- Cinque Terre
Day 6 Lucca area -- Florence day trip
Day 7 Lucca area -- Garfagnano, other ?
Day 8 Drive to S. Tuscany/W.Umbria -- via Pisa, Siena
Day 9 Tuscany/Umbria
Day 10 Tuscany/Umbria -- Perugia, Assisi
Day 11 Tuscany/Umbria -- Orvieto?
Day 12 Tuscany/Umbria -- Day trip to Rome to visit friends
Day 13 Tuscany/Umbria
Day 14 Drive or train to Venice -- (from ?)
Day 15 Venice
Day 16 Leave from Venice

Does anybody out there have a rational, fail-safe itinerary to recommend?
Recommendations on where best to base in each of these areas?
How about favorite towns, lodgings, sites, or other specifics in the vicinities?
Something else I should know about?

Thank you! I value and appreciate your experience and advice.

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