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Italy itinerary - input needed, please!!

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Hello! I’m in the beginning stages of planning a trip to Italy. We’d like to go in April or May 2018. We love history, museums, architecture, art and scenery. I’ve been to Venice and Rome in the past. We will have two weeks (arriving day 1, departing day 15). I have a rough idea of an itinerary, but would appreciate any input and insight. We would like to see Venice, Florence, Tuscany (Sienna, Volterra, Cortona, Montepulciano, Etruscan sites and hot springs) and Umbria (Assisi, Orvieto).

I’d love to see the Dolomites and this is where I’m stuck. I don’t want to completely rush the trip, but I don’t think we will return to Italy in the future so I don’t want to regret missing it.

Here are my thoughts:
1 - fly into Venice, drive to the Dolomites then drive to Umbria then Tuscany, drop car in Florence and fly out of Florence
2 - fly into Venice, drive to the Dolomites, drop car in Florence, visit Florence, rent car again, drive to Tuscany, then Umbria, fly out of Florence (dropping car at airport)
3 - fly into Florence, see Florence, rent car and drive to Tuscany, then Umbria, drop car in Florence, train to Venice, see Venice, rent car at train station, drive to Dolomites, drop car at airport, fly out of Venice
4 - fly into Florence, drive to Tuscany, then Umbria, Dolomites, Venice, fly out of Venice
5 - fly into Florence, drive to Tuscany, Umbria, drop car in Florence, train to Venice and fly out of Venice – leaving the Dolomites out completely :(

Thank you for your help!

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