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Enough time to make it Fiumiccino to Milano Centrale via train?

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Hi there, I apologize for positing what seems to be a common question but I have a few different details.

My bf and I will be arriving in Fiumiccino from Split, Croatia on Iberia at 16:20 p.m. We are both US passport-holders and we will be checking baggage.

We need to get to Milan that evening, as we fly out from there to the US the following day at 4:30 pm. I'm using the ItaliaRail website which combines the Leo Express train and the high-speed from Rome. It seems we have two options:

One: Leo Express departs Fiumicinno at 17:27 and arrives at Tiburtina at 18:15 and from there a train to Milano departing at 18:29.

One: Leo Express departs Fiumicinno at 18:27 and arrives at Tiburtina at 19:15 and from there a train to Milano departing at 19:29.

Taking into account the entire customs process and bag delay, which train would you take? There are no later trains. I'd obviously prefer the earlier one to have a little bit more time in Milan before bed but I want to make sure I have enough time to make it.

Thank you!

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