Venice or Milan

Michael is absolutely wrong about no nightlife in Venice. You just need to know where to look. On the weekends the young crowd gets together to hang out at the plaza near the Rialto Bridge (before the fish market). Music blairs as everyone hangs out in the open plaza surrounded by many small bars. We stumbled across the area by accident and stayed to hang out with the locals as everyone was having such a good time.

Venice all the way, no way would I ever have taken any of my daughters to Milan as it's really nothing special.

If your boys are old enough to want a city teeming with nightlife, Venice is not it. The population of the entire island is only about 60,000. After about 9 pm, it turns back into the small town that it actually is. There are a few places (noted above) that do have some nightlife for the locals and some tourists and maybe they'll be fine with that. If your boys are under 18, Venice would probably be a lot more fun for them. Milan is big and urban, with lots more young people.

It's important to know what your boys' interests are.

My boys are 23 and 21 - they are all about night life!

But Venice is sooooooo cool, with or without "nightlife" as we know it. Milan is a big city wth old buildings. :-) Snottiness aside, they will find places to hang out in Venice. How late? Maybe 2300 or Midnight. But during the day, wow!

23 and 21? Um, Elizabeth, your boys are no longer teenagers. :-) Venice is definitely not known for its nightlife (except during Carnival), but it is indeed beautiful and they would probably enjoy it. (It's one of my favorite places.) But have you considered Bologna? There's a huge university there and it's a great place to visit and very, very hip. I wouldn't drop Venice, but maybe you can add Bologna? And it's considered to have the best food in Italy.

I had an opportunity to attend a conference in Milan late last year. My initial scanning of the internet for things to do left me somewhat dubious. I went anyway and absolutely LOVED Milan. Very walkable, easy to get around on the subway, loads of things to see. Great people watching too. Also, easy to do a day trip to Como or Venice. Enjoy!

On the other hand, Milan is the fashion center of Italy, and presumably full of hot young supermodels.

For young men, I think Milan would be much more appealing. Previous comments are correct. Venice shuts down aside from a small area just across Ponte Rialto, which is very happening. Milan is a big gritty city, but has young population, is easy to get around and has endless beautiful Italian women and fashion to look at for their age group. If you choose Milan, be sure they bring fashionable clothes. It's easy to spot American tourists. They are the only ones under 50 dressed sensibly (to us at least).