The odds are in your favor that you'll have a southwesterly wind so you could free the sheets outside Rockland Harbor, and head due East. You'll likely beam to broad reach straight for the Fox Islands. There's a good chance you could sail all the way through, but stop for a few hours, or overnight and go into North Haven, hike Vinalhaven, spend the night in Perrys Creek or a number of other harbors in the area.

Sail on eastward through the Fox Island Thoroughfare and back into Penobscot Bay. Carry your heading, due east, into the the Merchant Islands off Stonington. Spend as much time as you can threading your way through these wonderful islands dotted with fine anchorages.

You could do this route in a few days nicely, or easily spend a week and rarely need your engine in prevailing summer winds.

If you have the time, keep on going through Jericho Bay toward Mt. Dessert. Too many places to list really and I can't think of any I would avoid. Even over hyped Pulpit Harbor will likely surprise you with it's beauty.

This route can be made either side of the Fox Islands as well, taking advantage of slight slants on the southerly breeze. It's a route for sailors.