Paddling Islesboro to Stonington is a pretty big day, and currents matter, but it is pretty. I've typically gone around the South end though, not the North. Far more Islands and interesting waypoints along the way if you go around Pendleton Point, then on towards Spruce, Butter, etc. There are some camping options along the way too.
The crossing from Eagle to Deer Isle is not insignificant, and involves current and boat traffic. I encourage good preparation and caution for anyone doing crossings like that.
(This message, by the way, typed on the north east end of Islesboro, where I happen to be visiting my folks tonight.)
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