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27 Days in Italy

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My Family and I are planning to spend the month of August in Italy, our itinerary is as follows:

July 30 Fly into Rome
July 31 Fly/train ? to Pisa
July 31- Aug 2 - Pisa
Aug 2 -5 train to La Spezia visit Cinque Terre
There not sure how to travel through the 5 cities Is by bus or train or a tour ?
Aug 5 Cinque Terre to Milan by Train.
Aug. 6 - 20 - 15 days Tours with Go Ahead Tours
City to visit are Milan, Como Lakes, Venice, Florence, Assisi, Sorrento, Rome
Aug 20-22 Explore Rome
Aug 22 Fly/Train to Palermo
Aug 22- 26 Explore around Palermo
Aug 26 fly/train to Rome
Aug 27 Fly home

Does this look like too much to do or is there better place we should visit, it's my husband, my son who is 14 and I travelling, we like to visit museums but not every day, we enjoy the beach and also like to just walk around and take in the town. While we are on our own the first and last week we are looking at staying in Airbnbs. I would welcome any tips you have to offer.

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