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Train tickets

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We are travelling by train from Rome to Florence on June 18th. There will be 5 of us. Would it be better to purchase tickets now online through Trenitalia, or wait until we are there and use a kiosk? We will also need to get from Florence to Venice later in the week. Or, is there another travel option I'm not considering? We aren't too worried about a particular time, other than preferring to leave in the morning. Thanks!

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