In a 20 footer you're not going to go around Monomoy so I assume you're going West to the canal
then across the Bay?
I'm assuming no cuddy so no place to sack out while your relief takes the helm
. I would say def. doable in a series of day hops. Easier if you have a kicker
and a bit of fuel
would be a must and once you get downeast the fog
may be more of an issue than anything else. If you do it, write a book about it. It would be a good story.
I have an O'Day Mariner in Chatham and have planned a down east cruise
in a bigger boat for years so I have a good mental picture of what you want to do.