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Revised Itinerary/Draft 2: Milan, Venice, Tuscany, Rome help

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After thinking more about my last post and doing airfare research, I am going to be booking a round trip, nonstop flight to/from Milan with Emirates for two weeks in October and have also added a few more days to our trip. Although I'm not too interested in Milan, the nonstop flight to Milan was $400 cheaper than other nonstop flights that would have gone to Venice or Rome, so the cost savings ($800 for both me and my fiance) is worth the hours we'll have to spend on the train getting from Milan to Venice, then Rome to Milan. Plus the flight is only 8 hours vs 15-20 hour flights. I would rather spend more time on a train than have a terribly long flight or layover/connection.

Since I will be flying into and out of Milan, can anyone offer any advice on the draft itinerary below? I would like to fly into Milan, then train to Venice for a few days, then rent a car for Tuscany (day trips to Siena, San Gimignano, Montepulciano, Florence, Orvieto etc), drop it off in either Orvieto, or Florence, then train to Rome ( or just drop off the car in Rome at the Rome Tiburtina station) for the remainder of the trip before taking a train to Milan on our departure day for our flight home. We both agree that we would prefer a rental car to have the freedom to explore Tuscany without adhering to any particular schedules.

*My question is, where should I pick up the rental car after Venice and before Tuscany? Also, are there any places we should stop or stay overnight to make the Milan/Venice, and Rome/Milan portions of the trip more bearable/fun? Milan/Venice and Rome/Milan seem so far from each other so I was wondering if there's anywhere we should stop in between those. Lastly, since I added a few days to our vacation, how many days would you put for each place?

Here is the current draft itinerary:

Day 1 Oct 5: Departure day flight 10:20 pm JFK to Milan
Day 2: Arrive Milan around 12 pm, immediately train to Venice to arrive around 4-5 pm
Day 3: Venice
Day 4: Venice
Day 5: Leave Venice, rent car somewhere then drive to agriturismo in Tuscany, not sure where yet (perhaps near Pienza, Siena, or Montepulciano?)
Day 6: Tuscany hilltowns
Day 7: Tuscany hilltowns, possible Florence or Orvieto day trip
Day 8: Tuscany hilltowns
Day 9: Leave Tuscany, drop car in either Orvieto or Florence, train to Rome, (or stay in Tuscany 1 more night)
Day 10: Rome
Day 11: Rome
Day 12: Rome
Day 13: Rome
Day 14: Rome
Day 15: Oct 19th Train to Milan in morning, 4 pm flight Milan to JFK

I'm torn between leaving Tuscany on Day 9 or Day 10.

Thanks in advance for your help!

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