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Italy with 2 parents, 4 young adults and a 5 year old

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As you can see, we have a mixture of ages and interests. We are just beginning to plan our trip to Italy in May 2015. I am looking for any tips you are willing to provide. My top questions would be:
1. What exactly should we see? The young adults will be with us for 10 days, then we will continue on our own for another 10 with the 5 year old. We don't want to rush our trip, so have to narrow it down from the 5 cities we have (Venice, Rome, Florence, Sora (my husband's birth town) and Positano).
2. I am thinking we should be looking for apartments rather than hotels. Is airbnb the best resource for this?
3. Any other advice you can provide us for this type of group would be appreciated!

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