I'm not sure why more people don't. Having done it, I can attest it's a good way to sail Maine if you aren't a full time cruiser. There are some risks, not the least of which, you may end up living here.
Stumbling on this ad for moorings in Bucks Harbor, it got me thinking what a great way this is to break out of the typical range most owners are confined to because they don't have or want to spend the time onboard to get to a new cruising area,... and back.
This enterprising young lobstermen will set a new mooring for you, there's space in Bucks Harbor(well protected). The annual town fee is 40.00 dollars(not a typo). You'll pay for new tackle, yearly inspection, you're all set. http://www.penobscotlobstertours.com/moorings.php
Why Bucks Harbor? It has a lot going for it. Getting here, you stay right on 95(little summer traffic), get off around Searsport. Is that about 5 1/2 hours from Boston?
Long drive? No! Not to be sailing in a world class destination. Round trip from Boston in your boat would take a week(if you're lucky), with few or no stops, and you'd do most of it under power.
Bucks Harbor is at the mouth of the Eggemoggin Reach. That means you're ready to sail(sail, really sail) in most any weather to a near limitless number of new destinations, within a few hours. Penobscot Bay and east to the MDI area are connected and mostly protected. There's a near natural loop around Penobscot Bay(which Bucks Harbor is on), that can take advantage of almost any wind direction.
You could also rent a seasonal mooring from Bucks Harbor Marina(you'll need to rent dinghy space and maybe a parking space from them anyway).
Walking up the hill from Bucks Harbor several years ago.
Not the only option, many harbors in Maine can be turned into a seasons(or more) home base for your boat. We used to drive 8 hours to some Maine harbors where we kept our boat. With some long weekends, a couple weeks vacation, we'd spend a month onboard sailing to some wonderful destinations on this coast. Our kids never complained about those drives.
When in Bucks Harbor, you can walk up to "The" store, and sit outside for breakfast. It's a quiet place.
Good public trans options exist up to the Penobscot Bay area, you don't even need a car. Anybody else doing this now or in the past?