Last week I came back from a 6 day buying trip. I went with a girlfriend, for her this would be her first trip... for me this would more times than I have fingers.
The plane trip itself was exhaustive as we had to transfer 2 times and had some unexpected layovers. Once we got there we hit the ground running. We hit Duomo, Monte Napoleaone and Spiga right away. Those areas are really the center of the world when it comes to shopping. They have like 3 Prada shops in the same block! Italian made stuff is generally cheaper than in Canada and when you factor in all the various taxes and duties, we still come out like 30% cheaper than Holts.
I really like Bottega bags despite the brand being older, I found one that wasn't all old lady like and snapped it up. I must say this trip I was the ideal of self control, I only bought a few things. My GF on the other hand went hog wild. For fear of reprisals from her husband, let's just say she did very well.