Yes, I think it's good to see different areas in Italy, as they are all beautiful yet have such a different 'feeling'. I was one who was overwhelmed by Rome on my first visit and could not wait to get out of there. I've since been back several times and really grew to appreciate it's charms.

If you stay in Venice only, you could day trip to Verona, Padua or Vicenza.

Most of the tour books do a Rome, Florence, Venice combo in 10 days. Fly into Rome, out of Venice. If you could arrange guided tours of Rome and Florence, you would, IMO, optimize your time there (someone else buys tickets, etc.) and end up in Venice with no cars and only magical buildings seemingly rising from the canals.

OR Fly into Florence and rent a car to a Tuscan base of your choice and end up in Venice.

Hey, I like the idea of starting in Rome and then heading to less crazy destinations! We will definitely do open jaw tickets. It would be nice to end up in Venice. As I said, I am not a huge fan of Florence, so prefer to skip it. If we decide to do Rome to Tuscany and then pick up a car, would anyone recommend training to Florence or Chiusi (sp?) if our destination is the Montepulciano area? We could drop the car off there and then train to Venice to end, maybe. I don't want to spend the whole trip in one place and do day trips. This may be her only trip to Italy.

The only issue with departing home from Venice is that the flight out will probably be super early in the morning, and getting to the airport might not be super easy at that hour. It's easier to catch an early flight from Rome on the way home I believe.

I am travelling to Rome in 2 weeks and then taking a train to Chiusi. I am renting a car from Aesserent,
They are right across the street from the train station. I have not rented from them before, but they have great reviews from those who have. They have been great to communicate with via email, and are very prompt in responding.
<[email protected]>

One more note. Chiusi is only a few kilometers from Montelpulciano, and not far from Pienza and Montecino.

Sorry, actually Montepulciano is about 12 miles from Chiusi.
From Montepulciano, you are close to many great hilltowns, ie, Pienza, about 5 miles, Montelcino about 15 miles, and you will find many, many, other great towns when you get lost.

easy enough for me to say ... what do I have to lose? ;)

But I would fly into Venice, spend however many days seems right to you (or your friend - ask her daughter) and then go straight to Rome for the remainder of your time in Italy. Fly out of Rome.

I know, I know - there is so much more to Italy than Venice and Rome, but for a first timer, you can't go wrong with those two. And you could include day trips too.