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Italy - May OR September??

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My husband and I are trying to plan our next trip to Italy! We want to go to Rome and the Amalfi Coast this trip... We could go for 2 weeks mid to end of May OR mid to end of September. I know now I can get the time off in May but won't know if I can get the time off yet for September. Airfare seems about the same for those times. Any advice would be appreciated! thanks!

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