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Planning a Trip to Milan ending in Florence

I am planning a trip to Milan in March of 2025. We have 10 days and want to visit Milan, Verona, Venice and end in Florence by day 8. Any suggestions on when to train and when we should rent a car. We are looking at 1.5 days in Milan, then train to Verona.. Stay one day in Verona then travel to Venice. Stay in Venice for two days, then travel to Florence. We want to visit Florence to visit a winery we know, and other time visit possibly cinque terre and montepulciano.

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With all due respect, given the time required to travel from one place to the next, you won't really have time to visit the CT, and in any event, March is a bit early for that. All of your other cities are efficiently reachable by train, except for Montepulciano. A rental would be most efficient for that. Given the low legal limit for blood alcohol, any winery visits should be done either by a day tour, a hired car and driver, or by a designated driver. Remember that all drivers in your party will need an IDP.