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NYC to Prague; Prague to Italy

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We're planning a 12-day trip in mid-May. There are 4 of us traveling--1 will already be in Europe and 3 will be coming from NYC. Two of us are using frequent flyer tickets and 1 is buying a ticket. We're looking for alternative ways of getting to Prague, given that the FF tickets seem to require lots of layovers and stops and the purchased ticket seems like it will be a fortune. After Prague, we plan to go on to Rome and Florence. I'm trying to coordinate 3 different versions of the same trip (the 2 FFs, the 1 paid, and the 1 who's already in Europe) and I'm so confused I can't think straight.

Here are the questions:
--Would it make more sense to fly to Frankfurt and then take the train to Prague? About what is the cost per person?
--What is the best way to get from Prague to Italy and it is best to start in Rome or Florence?Large international carrier? Regional airline? Camel? There will be 4 of us traveling together at that point.

Any and ALL suggestions are welcome! Thanks for any info you can provide.

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