Bellagio!  If you are flying into Milan it is an easy trip to Bellagio on Lago di Como.  You can take the train to Como and a boat to Bellagio.  It is a beautiful boat ride around the lake.  The boat makes a number of stops in small towns as it makes its way to Bellagio.  The other option is to take the train to Varenna and the ferry back to Bellagio (it is about a 10 minute ferry ride).  Both boats are very comfortable.  Once you are in Bellagio there a lnumber of excellent restaurants and fun shops.  You can hike around the town or take the boat to neighboring towns to walk through villas or enjoy scenic hikes.  Some people prefer staying in Varenna, but I am a Bellagio girl myself.

Cinque Terre - especially if you like outdoor activities.  You can hike if you are energetic or take the boat to go from one village to the other.  My favorite village is Vernazza, but it is not easy finding accomodations there.  You can stay in Monterosso, which has more roms available and more restaurants and visit the other villages.

If you are going to Venice stop overnight in Verona.  If you are taking the train to Venice you will stop in Verona anyway.  You can have a quiet, relaxing evening before you experience the crowds of Venice.

Italy is full of cities worth a visit. I'm not saying that just to advertise Italy, but I'm saying it because every city has a unique, beautiful and interesting aspect. Venice is amazing for it's architecture, and connection with water. You are on a city build over 1XX islands, connected by bridges. And all this was done before the industrial revolution, after the barbarians invaded Europe.
You may not want to miss the Italian Alps. Cortina and Santo Stefano are both good places by experience, by I'm sure any other town on your way by train will be just as great.

You should visit some of the smaller towns like voltera, Montalcino, Montepulciano, Cortona and Lucca.  Avoid San Gimignano - it is packed with tourists and tour buses.

my fist trip was in italyyyyy, in perfect place such Umbria....
fresh air e everithing is green---- with my friend we have reserved an splendid castkle of 13th century http://www.todicastle.com/
my vacation was amazing!!!
umbria is fantastic

Hello Steve,
For me you should go to Verona, which besides being a beautiful city is the famous Arena. In addition if you like the writer Shakespeare and you read “Romeo and Juliet” you can find the house of Juliet in Via Cappello where tourists come from all over the world to see. If you want I suggest an Italian site so you can see the city: http://it.wikipedia.org/wiki/Verona
Fanny Perlene

You can't go to Italy and not go to Rome.