Go in September, it is the best month. Never in August. Land, drive, arrive in Venice. Book your tickets for the Venice Film festival in advance. Yes, you can go. Yes, you will see George Clooney.
Take a boat to the Lido di Venezia. Eleven km of beach.
Eat here. Risotto al nero di seppia, trust me.
Drink a Spritz in the shadow of the pine trees.
Go see a movie. Say hi to George Clooney.
When the festival is over, drive or take a train to Lucca to see the candle night. But try to be there one day before, for the repetitions. It is magical and not crowed.
Stay awhile. Rent a house.
River Cafe Cookbook or this Italian one.
In town buy bread and pizza bianca here and ice cream here.
After head north to Liguria. Everyone wants to go to Cinque Terre. If you never did, stop here. If you know it, visit Alassio also. The beach there is one of my favorites. Gorgeous. Eat ice cream here.
One of the best hotel of this region is in Camogli.
When you have to, and only then fly out of Milano. But stay an extra day. Just after the holiday the city is at his best. The people are finally relaxed, and everybody is outside catching up. A chiacchierare. Sleep here. Or in the new W. Eat here. And of course shop at 10 Corso Como, Max&Co and Via Montenapoleone before leaving.
Done! Ciao, Have a great weekend everyone.