Sure I'm biased, but with good reason and experience. First Larry, there's not much difference, time/distance wise, to making landfall in southern Maine. With your boat, if you can hit a good southerly (odds are in your favor), it would be an easy overnight and a sweet sail.

Once you're in Penobscot Bay, wind direction and strength are not the issue they are on the coast. You can go up the bay, through the bay, around the bay, through various beautiful sails. And you can move through to the MDI area if you have the time even with winds that might keep you pinned down in southern Maine.

The old rule of thumb to allow 2 days going southwest to 1 day going Northeast is a good planning tool. This is the time to enjoy points south, always being ready to launch off on a north wind or better yet, a hot westerly off the land.

With your schedule, think about leaving the boat just in case. Take advantage of good trans options, planes, trains and buses from the Penobscot Bay area.(perhaps leave the boat in well protected Rockland for a return the following week). Also very good connections here for picking you up at the boat and getting you to nearby Owlshead airport or even Portland for the train or bus.

Penobscot Bay is an easy commute to points south thanks to these public trans options.