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Help needed with itinerary - Florence, Cinque Terre, Montepulciano

I wonder if anyone could please offer some wisdom on our travel plans?

As part of a wider (slower!) trip in Italy, we have four nights between leaving Florence on a Wednesday morning and arriving in Rome on a Sunday afternoon.

We have two nights booked in Montepulciano (Wed and Thurs), and are considering spending Saturday night in Manarola on the Cinque Terre. Friday night could be in Siena or we could stay in Montepulciano for a third night.

My questions are:

1) Does that seem reasonable / doable? (I know its quick but I'm not sure if/when we'll ever get back so we're keen to try and see all these places, even if just fleetingly). Or are we being to ambitious / greedy, and should we drop plans for the Cinque Terre?

2) Are we better visiting those places in a different order, in terms of transport?

3) Where would you recommend staying on the Friday night?

4) I would prefer to arrive in Rome by train, rather than car, but am unsure where to drop the car when Rome-bound from La Spezia. I could hire the car in Florence, drive to Montepulciano, then return the car at La Spezia before catching the train to Manarola; after leaving Manarola should we take a train from La Spezia all the way to Rome? Or am I better to keep the car parked at La Spezia until after Manarola, and then return it to Florence or Pisa on the Sunday before jumping on a fast train to Rome (bearing in mind not all car hire locations wil be open on Sundays). What would be the least complicated route?

Thanks very much, in advance.

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