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Prague to Vienna then maybe Trieste then Lake Como

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I'm planning a trip for 2016 for a large group of my immediate family as well as some extended family. It would comprise 6 middle aged adults, 3 young adults and 2 teens.

We are hoping to cover a lot of ground since this will be a first trip to Europe for many and only the second trip for the rest of us. We know that we want to start by flying into Prague and finishing in Lake Como area (flying out of Milan). But the in-between is the question.....

I'm suggesting to the group that we do four satellite cities with four day stays at each for a total of 16 days. Perhaps Vienna, Trieste, Salzburg, Munich, somewhere in Switzerland as the in between places.

There is a great deal of interest in WWII history as well as anything historic as well as being outdoors (walks, biking, views, etc).

We are hoping to find accommodations thru VRBO. We did this when we were in Italy in 2011 and got a great apartment in the heart of Florence. Loved it!

Here are the questions:
What is the best way to travel with a group this size for this proposed route?
Would it make more sense to break it into two satellite cities with a week in each (and then do day trips from there?) given the logistics of hurding cats through Europe?
Is there a place or route that is a must see?

Because of the teens, we will have to go during the summer months, is there a better time than others? Words of advice? I do know that it is the worst possible time re: crowds, etc but I can't see a way around it.

Any help, suggestions or ideas are appreciated. We are super early here just trying to figure out the big idea logistics right now.

THanks!!

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