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Is this realistic... advice?

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Aloha all,
New to the site, so hopefully I am posting my questions in all the right places. My husband and I are from the U.S. and looking to take a 2-month backpacking trip across Europe from end of July to end of September.
So far the plan is this:
Ireland - 7 days (rental car) Dublin to Dingle to Galway and back
Scotland - 5 days (rental car) Glasgow to Isle of Skye to Inverness
England - 5 days (subway/tour bus) London
Belgium - 3 days (rail/walk) Brussels flower carpet to Bruges
France - 9 days (subway) Paris to Bordeaux to Burgundy
Switzerland - 6 days (rail/??) Geneva to Grindelwald
Italy - 11 days (rail/walk) Rome to Florence to Venice
Austria - 3 days (rail/walk) Vienna
Poland - 3 days (rail/??) Krakow
Czech Republic - 3 days (??) Prague
Germany - 4 days (rail/walk) Munich Oktoberfest
My husband and I are both in our early 30's and this will be our first trip to Europe!
Any advice on best mode of transport/hostels/favorite hole in the wall diners or must-do trails? Also...any tips on which electronic devices we should bring and best ways to Skype family throughout trip? All responses will be read and greatly appreciated.
I've noted above in parenthesis what we had planned to do w/transportation...is there more than 1 rail company, that part seems so confusing to me.

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