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Apart from getting pickpocketed in Venice, my Italy tour went fairly well. Unfortunately, I spent a couple hours canceling my credit cards, but luckily my wife was there so we just used her cards for souvenirs, food and what not. Anyhow, despite the downs, there were a lot of ups like taking a gondola ride, going to the beach and seeing lots of beautiful women (don't tell the wife). great food, nice hotel, and a wonderful experience all around. 
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When I told my grandma I wanted to go to Italy, she sent me a brochure for PerilloTours, a place that specializes in Italy tours. I thought it was weird at first but then I read the brochure and was like, "well that's interesting," then the next thing you know I'm going to Italy six months later. We got a whole bunch of discounts and saved a lot on our tour of Italy. The accommodations were exquisite and we had a ton of fun. So, in conclusion, listen to your grandma!
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