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Trip to Europe October 2016

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Hi,
I am heading to Rome in October of 2016 for my brother's wedding. I am hoping to take off two weeks to explore more then just Rome....but want the best advice to where to go and how to accomplish this in an affordable way. I'd love to see Tuscany, Venice, Paris, maybe Greece? Looking for best flight times to purchase.....best set up for getting the most out of this trip.

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