We are traveling to Italy in September for 2 weeks and want to go to Cinque Terre, Tuscany and Amalfi Coast. What is the best itinerary for these destinations and where should be fly in to?
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Chicago
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Fly into Pisa or Florence and out of Naples or Rome whatever you can afford.
From Pisa you can train to whatever town you want to stay in Cinque Terre.
From Cinque Terre you can train to at least Florence and figure where exactly in Tuscany you want to stay. Then from Florence you can train to Salerno the closest town to the Amalfi Coast.