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What are the hardest parts of planning a trip to Italy?

We are a family of four with two kids, ages 15 and 12. We’re planning a 10-day trip to Italy this October. We will fly into Rome and fly home from Venice, and we’re hoping to visit Rome, Florence, and Venice, while also spending three days in Tuscany.

What do you think are the hardest parts of planning a trip to Italy? What are the smartest ways to organize it?

There’s so much helpful information on this forum, but I’m not sure I’ll be able to keep track of all the details.

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