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trip of a lifetime advise

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My hubby and I are celebrating our 30th anniversary in the fall and wanted to plan a 2 week trip to Italy.
What are the must see's in Italy, we don't have an agenda yet and are trying to hit most of the beautiful spots. We like food and wine, countryside and nature, not so much into big city hustle, but do want to see some of the sights in Rome.

Has anyone done Lake Como to Sorrento, Rome to Venice and Florence in two weeks?

What's the weather like in north and south in mid October?

We are hoping for a romantic trip - Florence looks beautiful, what about Como area, is there enough to do in Cinque Terre to stay overnight?

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