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Tuscany, Venice, Bologna

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How does this itinerary sound?
Fly into Milan train to Venice - stay four nights since arrival date you really do not get much done due to jetlag (coming from U.S.). Then rent a car drive to Bologna and stay three nights, drive to Tuscany and stay five or six nights, back to Milan stay over night before flight home

We will be 2 adults, 19 and 17 yr old. We have been to Europe before, Paris, London, Italy
2001 we visited Rome, Venice and visited family in Sicily (I speak Italian)
2011 took a Med cruise visiting France, Malta, Italy, during the stops in Italy we visited Pisa, Rome, Palermo, Naples

Children were little when we visited Venice and they have an interest in seeing it again as they only remember bits of it

Husband is a chef and Bologna has been on his wish list a long time and also interested in visiting Parma and Modena, hence the car while in this area. should we make Bologna city center our home base or stay on the outskirts and visit Bologna. We do like being in a city center and be able to walk to dinner whether it is Bologna or a city nearby

Tuscany - We are thinking of staying near Siena, probably just a little south of the city so that we can visit both the Val d'orcia area and the Chianti region. Will probably do a day trip to Florence. I have been before but no one else has and they have an interest in seeing some of the major sights but we do not want to stay in the city

Hotel / B&B / villa rental - we are open to all options. Most important to us are that the rooms are air conditioned, we will be visting at end of June or sometime in July, and have internet access as I need to check in for work once per day.

I know we will need two rooms or a two bedroom apartment / house, etc
Recommendations for Bologna and Tuscany area?

While I would love to stay in Montepulciano everything I have read seems to say that you have to walk downhill to get to the restaurants and shops meaning that you have to walk back up steep hills to return to your room. I am not sure if husband's knees can handle the steep hills all the time and why we are considering staying elsewhere

Throw into the mix that brother inlaw and sister inlaw may want to join us, they have some mobility issues an hills will be hard on them

Given this information any suggestions on places to stay in Tuscany and Bologna?
Any city recommendations in Tuscany that we should consider?
Trying to narrow down where to stay then we can concentrate on searching for places to stay

Thank you

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