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Like I said, we've paddled Muscongous and parts of Penn Bay for a lot of years, have gone as far as Eastern Egg in terms of out there. If you are including that stretch in your trip, feel free to email me. We don't know Stinington well, usually have gone out to Muscle Ridge for an archipelago hit. But we are pretty good from Pemaquid Point to the (oops) WESTern portions of Penn Bay.
We have a group among which we have discussed the theory of doing the paddle out and ferry back thing to Monhegan (I got my Mon.... mixed up first version), but we have never been near having the critical mass of paddlers and skills to make the trip viable. So we never made it to the details of how to get the kayaks back.
to Islesboro (not Isleford--different part of the coast) is a good place to cross--it's about 1.5-2.0 miles to Flat Island then another half mile to Islesboro. Turn south then paddle down the west side of Islesboro to Grindle Point and Gilkey's Harbor--you can camp at Warrens Island State Park--
if you want to do a circuit trip, continue to Pendleton Point at the south end of Islesboro, the paddle about 7 miles up to "the narrows" portage across(about 100 yards) to the west side and back to Saturday Cove. Or go north, paddle around Turtle Head down the east side portage across the narrows and back to Saturday Cove. Another alternative is to paddle from Wadsworth Cove, near Castine from the east side of Penobscot Bay.
If you want to paddle up the coast cross at Saturday cove, go north around Turtle Head (north end of Islesboro)then cross to Wadworth Cove/Dice Head then across the mouth of Castine Harbor, down the side of Cape Rozier then about 1 1/2 mile to Pond Island (Penobscot, not the Pond Island in Blue Hill Bay)where you can camp--from there it is an easy trip to Deer Isle.
The only trouble with Saturday Cove is parking--it used to be open to all, but the last time I was there, a sign was up saying parking was for local residents only---that was in 2008 it may have changed or may not be enforced. Alternatives are Lincolnville Beach and Bayside (about two miles north of Saturday Cove) I have paddled from the mainland to Islesboro many times. It gives you an open water-sea island paddling experience but is not the epic that paddling to Vinalhaven from Rockland is. If you want further info send me a private e-mail