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Europe in 5 month

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Hi, my wife and I are in the initial stages of planning a 4-5 month trip to Europe from Boston US.
Starting next December (2015), we would like to see the following countries (not necessary in this order):
France; Belgium; Germany; Vienna; Prague; Budapest ; Italy/Sicily; Greece; Turkey; Cyprus Israel.
We were thinking to start in France or Germany and end our trip in Israel to be able to relax somewhere on the beach.
I would appreciate any advise I could get from this Forum on planning such a trip.
What should we look at to cover all the logistics of such a long trip?
What cities should we visit in each country and for how long, is it worth it to go some of them?
We are not thinking of a trip on a shoestring budget, as we are not that young (late 50s). and would not have the stamina for staying in hostels, but we would like to have it on a moderate budget and get a good sense on what should we expect for expenses.

Thank you all.
Greetings from Boston.
Michael.

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