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30 day europe trip HELP!

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Hello all,

I am from new york, i am looking to do a 30 day tour of europe. Some places i would like to visit are santorini, athens, mykonos. from there i would like to go up the coast to croatia, cross over to italy start in milan and work my way down italy, cross over from sicily to ibiza. I m not sure if this route makes sense. Also i do not know how much time in each place i need to spend and how long it takes to get to each place. How do i book hotels? do i book it in advance or hen i get there ? how do i know where to book the hotel? and for what days ? how many days in each ? how do i get from one place to another? SOMEONE HELP!

thanks :)

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