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Rome, Florence & Milan In Late December


My friend and I would like to visit Italy in late December. Our tentative itinerary is like this:

1) Arrive in Rome by plane, 17th December Wednesday. Leave on 22nd December by train to Florence, on 22nd December

2) Depart Florence on 24th December and take a train to Milan.

3) Possibly travel to nearby places like Como, Venice by train

4) Depart Milan and return home on 31st December

My main worries are not being able to secure reservations on the trains as the Christmas week is a peak season in Italy? Would trenitalia operate on days, like Christmas Eve and Christmas? Do you think it would be a problem even if I book online in advance?

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You will have absolutely NO problems buying your tickets as you go, at each station, from either the window or the automated machines. My wife and I spent 21 Dec through 30 Dec in Italy this last Christmas, and this was ideal, with no crowds, no trouble getting any ticket we wanted, and no need to purchase in advance, and thus lose a little flexibility in your itinerary. We flew into Milan, spent a day there, spent two nights in Venice, 2 nights in Florence, and 3 nights in Rome, flying out of all Rome. All by train. Have a great time; Italy is certainly magical off-season, too. Buon Natale!