If you are going to Italy go to Venice during Carnival.
If Venice is normally magic, in this period of time you will feel like you are in a fairy tale, transported back at the time of the Dogi!
The Costumes you will see are so elegant and beautiful that you will want to wear one too! And you actually can if you like! There are places in Venice where you can rent one.
You can check the official calendar here and book one of the event you would like to attend (there are plenty!):
www.carnevale.venezia.it/en
There are parties and shows in the streets of Venice or in Piazza San Marco and inside most of the hotels (my favorite hotel in Venice is the Danieli). No need to go the day of Martedi' grasso, when there are too many tourists, I suggest going there any other day during the week.
In the hotels, if you like you can reserve your high tea or dinner like in the Baroque Period and take a class on how to dance the Minuetto:
Keep your eyes open when you walk in the streets of Venice: not only you will see people wearing precious costumes all around you...
...but you might end up finding unique boutiques like these:
(Photo: Pot Pourri, Calle dei Fuseri, Venezia)
(Photo: Bottega Veneta, Venezia)
Although I love so much the costumes in Venice during Carnival, I don't wear one since I was 10, but I recently bought this beautiful handmade Venetian mask, which I wore with a little black dress (this is more my personal style, chic but simple).
(Photo: Casanova and Enrichetta handmade in Italy masks)