Mike,
This is very ambitious, but looks doable with the right planning and conditioning. To date, the most miles I've done in one day is 29 on the water!
Here is that trip.
It was pretty rough at the end with the wind and I didn't have a sail setup then, wish I did.
Currently, I could probably do there and back without much additional training, but the additional days would be taxing.
I really like your plan though and this could be a special trip, very rewarding.
If I had a little more flex with work and kids I would be all over this. Maybe I can plan on 2019! Another thought would be to get some promotion or sponsorship on this event, maybe have the proceeds go to a local charity like HOW or something.
PS
If you do some training or wanna hit some offshore action this summer, I could be down. I've been out a couple times this summer. Only like 8 miles or so straight offshore, but nine mile bank could be a fun day!
Cheers,
Todd