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You could do maybe a few days in Tuscany and a few days in Rome. I wouldn't try to go to Venice or amalfi coast.
Milan was doable in less than a day. I suggest going to Florence for 3 or 4 days. I was in Milan for 2 days and wound up leaving the second day and doing a 12 hour tour to Lake Como.
I found Milan quite boring to be honest; you’d be better off flying in/out from there and taking a train elsewhere as other posters have said - Tuscany, Amalfi, etc.
If you’re going to be flying into Milan, I would recommend Turin and Florence. Turin is an hour train ride from Milan. One of Italy’s best kept secrets. Florence is about 3-4 hour train ride. A classic must-see if you haven’t been
Do it! I would spend a few days skiing in the alps if there is snow. Many other options within 3 hr of Milano. Florence and Venice are both 3 hr away.
Also not sure how cheap is cheap, but if prices are similar, I think there are other more interesting European spots to hit this season. What about Vienna, Munich, London?
Trust me spend the extra time in Florence! Do not spend more than 2 hours in Pisa.. Pisa is not the nicest of places, and the only thing to see is the Leaning Tower. I spent 3 days in Florence and then took a train from Florence to Cinque Terre with a stopover in Pisa (jumped out took a cab to the Tower, which was about 5-10 minute drive from the station). If you walk from the station with luggage it will easily take you 30+ mins, so the 8 Euro cab is worth it. Feel free to PM me for more italy tips. I’ve been through the whole country and my family is from there, so happy to help!
@M1 I think you can get a valuable Italian experience in that time if you have the energy and use your time well. That being said, of course you won’t get the whole country in 5 days, but you can still have a worthwhile trip.
I did Florence and Tuscany in 5 days. Totally doable and the perfect amount of time. Skip Pisa (from what I read) very touristy. You can day trip to Tuscany from Florence- highly recommend wineries: Casa Nova and Casa Emma.
Thinking next week
I would stick to Tuscany/Florence and cities north. Rome might be much especially if you need to get back to Milan for flight home
Additionally, you could stay in the north and do Venice, Turin, and the Asti/Alba region (wine). All manageable by train within 5 days
Italy is not a city it is a country. You can not do Italy in 5 days. Maybe 2-3 cities but then you would not see or experience much
Pick 2, maybe 3 cities. You cant do italy in 5 days.
@PWC2 I like Milan but I would not waste more than 1 day. It is a nice airport to come in if you would like to explore northern italy as there are direct flights from US
I would recommend 2 days in cinque terre, 2 days in Florence and 1 day in Milan (on the back end so you can catch flight back from there)... if it’s cheap, do it!
Thanks! Just booked this. Considering Florence/Pisa, and researching the other city I would do. Milan I would see in passing/ would just sleep there as of now. Traveling w non consulting friend who checks in bags 😆