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Final details of Italy Itinerary Advice needed

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I have most of our itinerary done but we have a few last details to work out and would like some advice on a couple of things. Here's what we have so far:

Fri May 29, Depart California LAX 8:45am
Sat May 30, Arrive Milan MXP 8:30am, train to Venice
Sun May 31, Venice
Mon June 1, Venice
Tue June 2, Venice
Wed June 3, Depart Venice, Drive to Montalcino
Thu June 4, Tuscany
Fri June 5, Tuscany
Sat June 6, Tuscany
Sun June 7, Tuscany
Mon June 9, Depart Montalcino, drive to Orvieto, train to Rome for one evening
Tue June 9, Depart Rome FCO at 10:0am

My first question is regarding which route to take from Venice to Montalcino. Should we drive along the coast through Ravenna and then go inland to Montalcino? Our hesitation to this route is that we already live on the coast in California, although we realize every coast is different and uniquely beautiful. Personally I love the Mediterranean! Or should we stop in Parma (or somewhere similar) even though the route is a little less direct because we really like good food, and cheese especially :) We just want to be sure if we go to Parma that we will really have the opportunity to see and try lots of cheeses and that a quick stop is feasable. We're not too concerned about the time either location takes since we have all day to get to Montalcino as we want to enjoy this day just driving south enjoying the views with a short stop or two. Neither one of us is really into spending much time in museums and such, nor do we like to have things too scheduled. We are more the kind who just enjoy being there eating, drinking, absorbing, relaxing.

My next question has to do with our one evening in Rome. I have been before and have seen all the major sites, however my friend has not. She knows she won't see much in this one evening but we do plan to have a walk around town to see the Spanish Steps, Trevi Fountain and the Pantheon, as well as have a nice dinner. I have narrowed our hotel stay down to two locations. One is right near the Spanish Steps, the other is closer to the Trevi Fountain. Does anyone have any feelings about which area is a better for one night? Or are they so similar that I should just choose based on hotel preference?

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