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Honeymoon in Italy: Venice, Tuscany/Umbria, Rome?

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Hey all!
I recently got some great advice on this forum from a bunch of people and have made modifications to booking our honeymoon in October. I'm looking for some final advice before finalizing plans and started a new thread since these are completely different questions and updated locations. Due to hotel availability/pricing/advice here, this is the plan of our trip:

Some questions below...

Our Honeymoon - October 9-21:

Arrive: Milan Linate Airport (10/9 at 11:00AM)
--high speed train straight to Venice--

Leg 1: Venice (3 nights, 10/9-10/12)
--depart Venice, train to Montepulciano area, stopping in Bologna along the way, not sure which train this would be or if it's worth exploring Bologna a bit?--
--pick up rental car in Montepulciano for next 4 days to explore? not sure what website to use or which town to pick up?--

Leg 2: Tuscany/Umbria (4 nights, 10/12-10/16)
--hotel not booked yet, looking to stay in central area for day trips, maybe Montepulciano? unsure of how overnight parking would work with our rental car in Montepulciano?--
--day trips to Siena, San Gimignano, Perugia, Assisi?--
--depart Tuscany/Umbria, drop off rental car outside Rome, then train in to avoid Rome driving?--

Leg 3: Rome (4 nights, 10/16-10/20)
--train back to Milan in afternoon for early morning flight--
Depart: 10/21 9:00AM from Milan

FULL MAP OF TRIP:
http://bit.ly/MYQcgH (green markers are priorities, blue markers are "nice to see",) agree with this?

Thanks so much everyone. I really appreciate all the help I've got here, you're helping me make the best possible trip for myself and my wife-to-be!

Dan

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