with a friend to celebrate getting my Maine Sea kayak Guides license. We launched at the Rockland Harbor Boat Launch at about 8:30 and paddled the three miles to Owl's Head.
After a rest and a bite to eat we paddled to Hurricane Sound, set up camp on a MITA island campsite at around noon (can't remember the name but it's in the guidebook) and spent the rest of the day exploring the area, including a stop at Hurricane Island,where I visited the HIOBS where I went in 1972 and Carver's Harbor. We got an early start the next day, and were back at Owls Head by about 10 am and the landing at 11:00.
The crossing from Owls Head to Huricane Sound is almost exactly 9 miles and even when visibilty is good you should follow a compass heading as the shore of the island does not contain any visible reference points which are visible from Owl's Head. The key to this trip is watching the weather. It was dead calm on our morning paddle out and a mild breeze (5 knots or so) on our paddle back. The calmest times are in the morning. By noon, a southwest breeze of any where from 10 to 15 knots usually picks up in the summer.
I couldn't tell from your post whether you were planning on doing the whole trip in a day or were planning a two or three day trip. It's an awfully long distance to paddle in a day (24 miles, 18 of which are essentially open ocean)although I'm sure others have done it. Better in my opinion to use two days, assuming the weather forcast is favorable. Have fun and be safe.
Touring Kayak Paddles
Full Size Sail Rig
The Kayak Wing
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