Great hiking in Acadia. The bus service makes it easier to get to different areas. You can spend quite a bit of time there and get to see many of the sailing areas you'd encounter on your boat.

You might consider a day trip or overnight to an island Jan. There are several. In my area of Penobscot Bay, Monhegan would be a great day trip. You'll get a sense of the sailing waters on the ferry boat out the 10+ nm's out to the island. Plenty of hiking trails, very interesting island and people. Do an overnight if you can.

Many islands in Penobscot Bay to the MDI area, have daily ferry service. If you have bikes, that's all you need. For a sailor, this may give you the best sense of cruising the area.

There's endless hiking in my neighborhood of western Penobscot Bay in the Camden Rockport area. The towns own miles of public trails on the shore as well as the mountains that overlook the bay.

As far as lodging in any of these areas, start with the usual web stuff until you find the areas you want to stay. Then refine by going to local sites.

Check Craigslist for vacation housing. You may find some single night places reasonably priced. There's always something on short notice. Location will determine price obviously.

If you find an area (Maines coastline is thousands of miles long and encompasses a small country for places to go), post again, someone nearby will likely have good recommendations.

Nice website, I've just had a look.