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Italy trip - play by ear or book everything in advance?

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Two week trip in Mid/Late May. Flight and hotel in Rome is confirmed. I'm torn on how much additional advance booking I should do. Will be travelling from Rome to Florence, Como area, Venice. I want some flexibliity for side trips in Tuscany or possible changes to our route, but am worried about hotels being sold out. Is it easy to change reservations or too much trouble and stress once you are there? I realize there isn't a lot of wiggle room on a 2-week trip, but wondering what you experienced travelers think. Thanks everyone...

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