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when to buy cheap tickets to Italy, especially open jaw

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Is it still advisable to buy airline tickets 6 months in advance to Europe to get the best prices?
Does purchasing tickets open jaw, let's say fron New York to Pisa, and from Venice to New York make a difference? I would think they are always more expensive no matter when you book. Instead of a multi-city search, if you search one way for each of these does it make any difference?

Do you think it is too late to plan such a trip now for September? Would a travel agent get the best deal?

Thanks

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