Progressive sailing trip - possibilities for summer

There is a post elsewhere for an event in Oregon that I would like to attend. However, with everything else on my plate, I cannot see going 2500 miles round trip for one event.
The thought occurs that if we created a succession of events, it might draw a crowd...
Suppose we start in Big Bear Lake, spend a few days, on to something in northern CA for a few more, then maybe finishing at Waldo Lake?
10 days sailing spread over three locations? Yahoo!
Maybe we organize around existing events, like a race in Ventura CA, then move on north afterward.
There are places in the southeast I would also like to sail, and if I dropped by Nashville en route, my kids would be all in.
Does this make sense to anyone else?