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Help planning multigenerational family Italy tour

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Hello! I'm in the beginning stages of planning a trip to Italy summer 2017. We'll be traveling with grandparents in their 70's, parents who are 40-something, and kids ranging in age from 11-16. There will be 12 people in our group. Between the age ranges, differing interests, and number of people in our group we are leaning towards taking an organized tour. We'd like a trip lasting 10-14 days. I'm a little overwhelmed about where to start but we are taking this trip to celebrate special occasions including milestone birthdays, anniversaries, and graduations so I want the trip to be wonderful for everyone. I'm thinking a Rome, Tuscany, Florence, Venice trip would be perfect. We have a healthy budget so if we decide on a tour group we'd like one that includes nice hotels in good locations, comfortable transportation, but a relaxed schedule with plenty of opportunity to see things on our own. We'd prefer meals to eat most meals on our own and take our time. Is such a trip possible with some sort of tour...we mainly are hoping it would make the logistics of the trio physically easier on the grandparents.

I'd also be open to other suggestions on how to plan a trip like this...I'm just not even sure where to begin. Is there a way we could comfortably organize a trip like this on our own??
I should add that our grandparents are originally from Italy and are native speakers so that will definitely be helpful...our mother does have knee and hip issues and we'd like to make the trip as enjoyable for her as well. They really are excited to share their home country with their grandchildren! Any suggestions, advice, or insights will be SO appreciated!

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