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Traveling to Europe with 14, 16 for the first time in June 2016

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We are planning a trip to Italy in June for 2.5 to 3 weeks. This will be the first trip for us with our kids 14, 16. I have never been but hubby has. Not sure what places to visit and stay. We like to travel slow and the less touristy the better. However with that said we love history and know that Italy is full of it. So we don't want to rule out all the amazing historic sites. Originally we were thinking about flying into Milan and starting at Lake Como with renting an apartment. Then moving south flying out of Rome. Or flipping that and flying into Rome leaving out of Milan. Hoping to visit AC along the way too. Any help would be awesome.

Thanks!

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