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Best place to take a new traveller in Italy? Plus cheap airfare questions.

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I am planning a trip for next year for myself and my boyfriend. I have done a fair amount of traveling (semester abroad in Rome + a few odd trips to Ireland), he has never left the country. Oddly enough, when I was in Rome, I didn't see that much of Italy, but rather used it as a jumping off point for other cities in Europe.

What would be a minimum suggested amount of time to go for? This trip would serve (somewhat) as a compromise between staying in the States indefinitely and going off to backpack in Europe for a few months. I have been wanting to go long-term backpacking for a very long time and find the idea of scaling it back difficult. I don't know if I would be able to talk him into taking off work for more that 10 days - is that sufficient?

Also, regarding the absurdity that is the cost of air travel: I don't live the greatest of hubs for international travel (Pittsburgh). I was wondering how good of an idea it was to try to save a few bucks by busing up to New York and flying out of JFK to Dublin, which seems to be pretty cheap, and then catching a cheap flight from Dublin to Italy - probably Pisa or Milan. The whole Pittsburgh - Italy trip would end up taking about two days. Is this insane? Doing this would save about $250, but would tack on an extra day at each end of travel. Is that an absurd tradeoff?

Honest advice is most welcome. Thank you in advance!

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