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Help in Planning Train Schedule Milan/Florence/Rome/Milan

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We are flying in and out of MXP in October 2015. We will need to get from MXP to Florence for 3 nights. Then we leave Florence and will need to take the train to Rome (staying near the Spanish Steps) for 5 nights. Then taking a train back to Milan for 2 nights ... Then home. We are flying from the US. We will not be checking luggage. How long should we plan to go through customs? And based on what I've read I should buy our train tickets in advance to get the best price. How far in advance should we buy them? Can you please give me advise on this, how to do this, how much time to allow once we land in MXP to make sure I choose the right time for the train? There are two of us traveling. Your help is appreciated. Thanks!

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