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Itinerary help - Venice, EMR, Tuscany

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My boyfriend and I have 9 nights in Italy in late August/early September, and I'm trying to figure out the best itinerary for us. We are skipping Rome on this trip due to lack of time and our goals - we want to trip to be relaxing, have beautiful scenery and very very food-centric (we are total foodies). We will probably do some cultural activities but it won't be the central focus of our trip. We are also flying in and out of Milan - I wish i could have done open jaw Venice and Florence, but the trip was booked with miles so we were very limited.

Given our goals, we are planning on 2 nights in Venice (I've never been and it's one of his favorite places) and then split our time between Bologna and Tuscany. This is the tentative itinerary I have - would love to get feedback.

Tue 8/27 - Arrive MIlan around lunch, take train to Venice and arrive early evening
Wed 8/28 - Venice
Thu 8/29 - Venice for most of day, head to Bologna by train in evening
Fri - 8/30 - Day trips to Modena/Parma (?), night in Bologna
Sat - 8/31 - Day in Bologna, night in Bologna
Sun 9/1 - Morning train to Tuscany, rent car, afternoon/night in Tuscany
Mon 9/2 - Tuscany
Tue 9/3 - Day trip to Florence, night at our base in Tuscany
Wed 9/4 - Tuscany during day, in the late afternoon drop off car and take train to Milan, overnight in Milan
Thu 9/5 - Morning flight back to US

We also need to figure out our base in Tuscany - we've heard it's great to have a car to explore the region, but also thinking it'd be convenient to be near a train station and not TOO far from Florence so we can day trip there easily. Also would want to get a good idea for where to rent our car when we're coming from train from Bologna (it also should be a convenient drop-off point).

Thanks so much for the help!


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