I'm looking for a 1-2 week expedition on the Maine Isl. Trail that would be for a couple of intermediate to advanced paddlers looking to avoid crowded campsites, day sailors, yachts, noisy campers, and cell phones! Also trying to find Maine kayak outfitters who rent glass boats for the expedition. We're used to paddling the big waters in the Pacific NW (Vancouver Isl., San Juan Isl., Glacier Bay Alaska, etc) are interested in exploring the MIT for the summer of 2010.

Any suggestions from fellow experienced paddlers?

Can I ask, have you joined the Maine Island Trail association? I think they might answer most of your questions in terms of difficulty level and crowds... campsites for many of these are reservable. Website is http://www.mita.org
I am frankly a relatively inexperienced paddler, but I know that sea conditions can change radically in the Gulf of Maine, and tidal bore can be surprisingly large (not that far from Bay of Fundy).