Any input on Revised Itinerary for first trip to Ital

So, is this what you are saying?
Rome - 4 nights
Florence- 3 nights
Vernazza-3 nghts
Montepulciano- 4 nghts
Siena- 2 nghts

The allotment seems ok but a little too much moving around for me but maybe you like to travel faster and do not mind all the checking in and out of hotels. Keep in mind that 3 nights is only 2 full days.
I might skip staying in Siena, although I love Siena but do it as a day trip from Florence and allot those nights somewhere else.
My main concern thought is getting from Siena to Pisa for the flight home. What time is your flight?
Also, do not count the day of arrival and day of departure as you usually do not have any time to do anything other than get there and get home.

Monday we take the train to Cinque Terre, most likely staying at Vernazza (it's Memorial Day that Monday, hopefully not an issue).

Exley, what are your travel dates? What we observe in the U.S. as "Memorial Day" does not correspond to anything similar, date-wise, in Italy.

Your point is taken on the busy agenda, but I'm hoping we've we've worked it out so that none of the travelling takes up more then half the day if we get early starts. The drive from La Spezia may be the exception. Our flight out of Pisa isn't until 8:15 at night, so I;m not concerned about that. We may even try to sneak a peek at the Tower if there's time.

I suggest combining your Florence and Siena days, staying in one city and day tripping to the other. I also see that currently your days in Florence are over a weekend. If museums are important to you, they're likely to be more crowded on the weekend (and one Sunday a month is free admission, Which can create a real zoo).

I have one other thought, which admittedly reflects only personal preference. I've had too many surprises on Italian trains to travel to Pisa on my flight day by train. I would be more likely to come in the night before, and plan on touring from Pisa on the day of my flight. Lucca is a nearby destination that's very nice.

I think it is a good itinerary. Your final day Siena to Pisa venture is reasonable unless there is a sciopero (strike). You can find out in advance at this site. You should have plenty of time to see the tower and have lunch.

I think it sounds good! Most of your stops are 3 or 4 nights. You only have one 2 night stop. IMO, this is a very comfortable itinerary. Enjoy!

There is nothing like Siena after the daytrippers leave, I love that you are giving it two nights. You can always take a short daytrip if you have time (aside from Pisa), but Siena is a great city with as much history as Firenze (but peaked about a century earlier).

Thanks to everyone for the great input. Kathy - I meant to say Liberation Day, not Memorial Day. Laurel - Thanks for the strike link. That will come in handy!