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Originally Posted by SportsJunky
If you are going to visit Florence (we loved Florence) from Milan, I'd recommend stopping in Modena which is on the way. The Enzo Ferrari museum in Modena was worth the time. There is a second Ferrari museum that is more focused on just the cars. I'd recommend it as well.
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I'll second Modena, but for a different reason. The food there is incredible (really, anywhere in Emilia-Romagna you'll find the best food in Italy). Stop in for lunch at Hosteria Giusti (they essentially invented balsamic vinegar) or dinner at Francheschetta 58 (Massimo Bottura's more affordable little sister to the best restaurant in the world, Osteria Francescana which is also in Modena).
If you're going to Modena, I recommend stopping in Bologna as well, 20 minutes away. Bologna is 38 minutes from Florence on the high-speed train. Bologna is a very cool town. Very medieval looking and the food there is amazing also. Tortellini in Brodo is my favourite dish and it can be found in my places.
I've been to Venice, not really my thing. Really crowded, food is not the best. Pisa I thought was a waste of time.
If you're going up to Lake Como, Lugano (Switzerland) is a very cool city to stop in. Maybe a 30-40 minute drive from Milan. We spent four days in Lake Como and on our third day we went to Lugano and liked it so much that we spent our fourth day there as well. We also went up to Bellagio and took a boat up the lake. It feels to me a lot like you're in B.C. around that whole region except the cities and towns have a lot more to offer.