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Venice to Milan with my family this July

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My two week vacation in Switzerland and Italy is nearly all planned and reserved thanks to the fodors community! All that remains to be booked is my rental car from Venice, which we plan to drive to Tuscany, where we will explore for several days. I want to return the car somewhere near Milan where we will stay for two nights. We have a 3pm flight out of MXP. I reserved the Last Supper viewing for 9:45 am the day of our departure.

I am traveling with my husband and two young teen girls (ages 13 and 14).

What I need help with:
Where do i pick up rental in Venice and where best to return it in Milan. Where to stay in Milan so that we can make the visit to the Last Supper and best make our way to the airport for our 3pm flight. Do we taxi to the airport on Wednesday the 27th of july or take a train or bus. For 4 of us, should we just do a taxi, or too much traffic.

A recommendation for hotel for a family would be great too!
Thank you

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