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Venice to Cinque Terre to Tuscany/Florence?

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My head is swimming. What with Fodors, TripAdvisor, and Rick Stevens I am going to go looney toons. Can someone help me put these pieces together?

We're going to going from Venice to Florence to Rome. For now, I'm trying to concentrate on the middle leg. We want to see the Renaissance art of Florence but also want to experience the rural nature of Tuscany. A vineyard visit and biking, for example would be idyllic. My daughter also wants to see Pisa, even if it means standing in line to climb the tower. Keeping in mind that we'll probably be on the train, would you recommend staying in Florence and somehow getting to the Tuscan countryside or staying outside and training into Florence. (And if we do that, would it be better to get a rail pass?) We're planning on spending 2 or 3 nights in the Florence area. I have seen a great tip on this forum that public transport seems to assume people go from the small towns to the cities in the morning and v.v. in the afternoon.

To further complicate matters, my daughter would like to catch Cinque Terre on the way from Venice to Florence. So we're planning on training from Venice to CT for one night and on to Tuscany Florence.

I suspect, this is trying to do too much with too little time. On the other hand, I'm hoping the training shows us someone of the countryside though we'd like to experience more of the "natural" Italy.

Ideas?

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