My husband and I have spent time in that area each summer for over 20 years.
Finding a nearest launch point could be challenging. Owls Head itself does have a park, but the beach is at the bottom of quite steep, tall cliffs. No launch point there - my husband and I have scouted it out. As you go further along the coast, towards Rockland, you can see even on a Google map that it is pretty much private homes and roads.
The nearest sure launch point for that trip is either Birch Point State Park further south/west, or going from a public launch in Rockland itself. Either means adding at least a couple of miles to the trip, and picking your damages between a more concentrated current to cross or messing around with commercial craft that are not expecting a kayak to be in quite that spot.
kayakmedic is dead on re the timing - in Penn Bay you have until 10am before things kick up in a way that increases the challenge. Most of this crossing in is bona fide open sea. That means dolphins, it is not rare for them to accompany the ferry from Rockland out, as well as a usual minimum of 4 to 6 ft seas.
One option that people consider is to paddle out and ferry back. But the ferries in Maine do not just keep running until everyone is back home, and even assuring space for one person and a kayak for the last trip of the day could require a reservation. They are small and operate in a much more restricted fashion than those in the NY and CT. In Maine is is not at all rare for an outsider to have to spend an overnight in their car on even the bigger island like Vinalhaven, because they did not understand the local system for assuring a space in the line for the return trip. We met one guy, a UPS driver, who kept ad apartment and a dog on Vinalhaven because he got stuck over there so often.
I know of one guy in Friendship who has a long time habit of this kind of trip, ten miles out to an island, once a month. But he starts at something like 4am and has not always been able to make the trip even with that timing and very careful planning.
Touring Kayak Paddles
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