Thanks, everyone for your feedback!
Snoozeman: I am probably not booking Alaska or anything long for this year. I will need to accumulate some vacation time, but who knows? How late is "too late" for Alaska - I see repositioning trips in September in various places, so I wonder if Alaska more or less shuts down then. I should really look at schedules, huh?
In the shortish term I am looking at Alaska and possibly a 3 day repositioning cruise to see how I like "at sea" days.