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Whoops I forgot to add this one - since you and your family is not into travelling much or should I say out of Skagway - do it from your livingroom or wherever.  This guy is a Canadian and did a trip from Alberta, Canada up the Alaska Highway up to the Yukon and then into Skagway, Alaska and back to the yukon into Whitehorse, Yukon and then on to North Alaska.  Really good photos of sites along the way.  Armchair travelling - cheap as you can get.  At the very least - it might help you in making a decision one way or the other.  Happy sailing!