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First timer to Italy help!

Flying into Rome,staying 3 days, next not sure if we should take train to Genoa or Lucca time allowed 2days or some place else on way to Milan. 3 sons ages 18 to 23 with be us. If Lucca thought we could rent car to see winery in Tuscany and Florence. Genoa visit a winery and the cinque terre area. After Milan by train and end in Venice. Looking for help and ideas with young adults. Once in a life time trip trying to make it the best i can. Trip is this spring. Thanks in advance for your advise.