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2 week trip to Europe (france, italy, switzerland & greece) HELP?!

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Hello

My family is planning to go on a 2 week trip to Europe mid-June to early July. (it's very short due to work schedules) My dad wanted to go to these four countries for the trip: France, Italy, Switzerland & Greece.

So I have a couple questions

1) Are four countries in 2 weeks feasible?
2) Do you have a timeline/guide on how which one we should go to first etc. (and if anything, where you would recommend going in terms of cities -- for france, we're most likely going to see Paris, Italy.. .maybe Florence & Venice, Switzerland... I honestly have no idea & Greece.. probably Rome)
3) if you have other suggestions or places that we must definitely see for these cities/countries, let me know.
3) in terms of transportation, what would you recommend? It's a family of three people. so would taking the train be better or renting like a car?
4) And if you recommend the train, what kind of tickets do we get/how can we get them in advance? (I live in America if that helps..)

Sorry there's a lot of questions... planning such a short trip to a huge place is a bit overwhelming..

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