Please help me plan our itinerary - Lots of questions!

I find it easier to answer your question than guess at the question that I need to ask you. First, have you put pins on the map so that you recognize the relation and distances? With jet lag and everything I would spent the first night in Milan. Remember the airport is about an hour NW of Milan. You would be lucky to be in car rolling south by 7 pm. Firenze would be a long drive and Bologna only a little shorter. Both are very accessible via train and Firenze is about the last place I would want to be driving at night with jet lag. You can be sure of getting the Italian welcome home gift about a year later as a reminder of your trip. Rent the car in Firenze.

Thanks, Frank. I didn't mean to imply I wanted anyone to guess at what questions to ask me! I just had asked so many questions on my original post, about each leg of our trip, it was too long for the board to post it. Pins in a map is a great idea, I didn't realize the airport was so far out. (Malpensa?) We also considered hiring a driver from the airport to our first destination, simply because of the jetlag, the not needing a car right away, and the unfamiliarity of the area. We did the same thing last time we were in Italy, flying in to Rome late, renting a car, and driving to Montepulciano. It wasn't bad, we'd do it again, but only if we were going to need a rental car right away. But no reason to rent a car if we did the CT first... So still not sure where to start...

After arriving in Milan at 5:50 pm, I wouldn't want to have the hassle of getting to the Cinque Terre by train that evening. And while, when I finally did spend time in the city of Milan after years of using it only as an arrival airport, I did enjoy the city very much, you already have enough places to go that you don't need to add it to your list for this trip. I'd say to begin your trip by taking the train to Florence (or Bologna, if you decide to add that, in which case, after spending time in Bologna, take the train to Florence). Upon leaving Florence, pick up a rental car for your time in north/central rural Tuscany. From there, head to the Cinque Terre; we've driven there, from Tuscany, with no problem, parking the car at the central outdoor lot in Monterosso (one trip) or at our hotel in Monterosso (Villa Steno, another trip). But you could also drive to La Spezia, drop your rental car there and take the train from there, if you like. Then get yourselves back to Milan by train or car to end your wonderful vacation. Keep in mind the recent severe flooding in the Cinque Terre; I don't know how much that will impact what you planned to do in there.

Thanks, Lexma. That makes good sense to do it that way. I think I'll post my other questions for the other parts of the trip on separate posts, rather than try to post them all on one. I should probably have done this from the beginning, but don't have a ton of experience on the board like some of the more seasoned veterans! It's terrible about the floods in CT and other regions of Italy. We will be sure to check it out as we make our plans. We'd still like to support the towns all we can.

you don't want a car for CT or Florence you need to narrow down where else you want to go I would only suggest a car for Tuscan area Milan has some amazing sights that should not be missed, since you are flying in and out of there do not miss them, give Milan a day or two give CT a few days and Florence I would give 3-4
Lucca and Pisa are a close connection between Florence and the CT if you are interested

I think Milan is worth at least one day. Although different from a lot of Italy it is worth taking a look. I have taken the train from Monterosso to Milan and you are looking at about 3 hours. Trip from CT to Florence is not much better. You might be best to fly into Milan, spend a night there, train to CT, train to Florence, rent a car, explore Tuscany, train back to Milan from Florence.

Billie, when I fly into a city in the late afternoon, I plan to spend the night there and get an eary, refreshed start the next day. Malpensa is about an hour from Milan, and you can easily take public transportation (shuttle or train) into Milan from the airport. I would suggest you spend the night there (I even pack a change of clothers in an outside section of my suitcase so I don't have to open it the first night). I agree that you won't really need a car until you want to daytrip away from Florence (trains and buses are very reliable in the area, and everyone gets to see the countryside instead of the driver watching the road).

Thanks, everyone, for your help. It sounds like starting off in Florence (or Bologna) is about the best route. We will consider staying a night in Milan and seeing some of it, but we have such a short window of time we will be in Italy, and there is so much that we want to do, we have to pare things down rather than add things in. Right now we are thinking: train to Florence, train to CT, rent car after CT stay, then see Tuscany region. I appreciate everyone's help... it helps clear up all the muddle in my head!

Thank you to everyone. We've decided to stay the first night near Milan airport and rent a car the first morning after a good night's rest (Thanks, Zoe, for the idea of having an extra set of clothes packed already to make it easier - funny how simple ideas like this never occur to me!) We plan on ending our trip in C.T. somewhere, as it is closer to Milan for our trip home. I appreciate everyone's help - thank you!

Billie, If you end your trip in the C.T., I'd suggest drropping your car in La Spezia, and then using trains into whichever of the five villages you choose to stay in. If you decide to stay in Riomaggiore, it's only about about 9-minutes from La Spezia. Use trains from there back to Milan prior to your flight home.