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Czech Republic, Austria, Italy trip

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Hi all! new guy here.

Me and my family are planning a trip to Europe from the US for 3-4 weeks. it will be their first time there, and they are quite excited. but, they don't seem to have a grasp about how to... go on about it. sure the flight and all is being planned and such, and I just might be the most knowledgeable.. but I need help.

We want to land in Rome, explore Italy, travel (by car) to Austria, explore and then travel to Czech Republic, and explore. A question that arises: I (myself) will be staying in Czech Rep. for a few more days after while they drive back to Rome for the return flight at the very end.

Question: Is it possible to get such an flight plan (for me) that has my plane take me (with family) to Rome, but my return flight flies to US from Czech Republic? I am not too knowledgeable when it comes to this.

Question 2: I know traffic is very much alive in Europe. How long are drives from Rome to Vienna, and Vienna to Prague? Estimates, of course.

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