Being asked to write about cruising on the coast of Maine in less than a thousand words is a little like being asked to write a single volume history of The World. It can be done but the result is likely to be so general and lacking in detail so as to risk being pointless.
What I can tell you in very few words is how much I have enjoyed cruising Maine over the past 36 years. I love Maine so much that in my younger more foolish days, I used to sail overnight to Northeast Harbour from Saint John on long weekends just for the pleasure of spending a night in that beautiful harbour. The coast of Maine runs, by the way, (north of) east and (south of) west. So if you are heading towards Cape Cod you are, in cruising parlance, heading west. If you are heading towards the Bay of Fundy you are heading east.
Speaking of Northeast Harbour, there might be a more beautiful and yachting-friendly community on some coast, somewhere, but I don't know of it. Mount Desert Island (MDI), on which it is located, is better known for Bar Harbour but Northeast Harbour is the preferred yachting destination. It has a combination of spectacular scenery, shelter, magnificent 'cottages', the proximity of supplies and services, public gardens, walking trails and the absence of shore-bound tourists that makes it the choice. When heading west from the Maritimes, it is on your route and it is the gateway to the Maine that we have all heard about. For those crossing from Nova Scotia, Mt. Desert Rock makes a great waypoint on your way to MDI.
This is not to suggest that there is nothing of interest between West Quoddy Head (the eastern-most point of the USA) and MDI, about 75 nautical miles away. But, notwithstanding Roque Island with its magnificent, and seemingly very out-of-place mile-long, white sand beach, much of Maine east of MDI is, given the fog, tidal range, currents, and cold water, so similar to the coast of the Bay of Fundy so as to be less of interest to me. I usually by pass it unless there is some reason to dawdle.
Rocky, bold eastern Maine contrasts with the low beaches and inlets of western Maine. This gets to the point of this brief missive: the coast of Maine is diverse in so many ways: wealth, population, topography, scenery, weather, temperature, boats to be admired and cruising appeal. No matter your taste, you will love it.
The so-called mid-coast of Maine, which I would define as bounded by Schoodic Point in the east and Cape Small in the west is the most popular cruising area. When heading west from MDI, which is just west of Schoodic Point, there are a range of cruising options: head offshore; pass inside the outer-most islands through Merchants Row; pass through Deer Island and Fox Island Thoroughfares on the way to Penobscot Bay; or head more inland and accomplish the same objective via Eggemoggin Reach. No matter which option you choose, and that may be dictated by wind and fog, you are sure to see more interesting yachts per square mile here than anywhere including the large engine-less schooners that take passengers on week-long cruises that are a postcard trade-mark of coastal Maine.
Whether it's the fishing villages of Stonington and Carver's Harbour, the summer communities of North Haven and Buck Harbour or the towns of Camden and Rockport, the range of shore-side experiences both simple and sophisticated is almost endless and the protected anchorages countless. Even further west is Muscongus Bay. It is often bypassed because of its half-tide rocks but the inside passages, islands and towns including Port Clyde and Friendship, home of the famous sloops of that name, are beautiful too. The area between Pemiquid Point and Cape Small with its famous rivers (Damariscotta, Sheepscott and Kennebec) is my favourite cruising ground though. Booth Bay Harbour is located here and despite its tourist reputation it should not be missed. It has great restaurants and a most hospitable yacht club. And on it goes.
And we haven't even touched on Casco Bay and points west of Cape Elizabeth where the coast is so remarkably different: low, flat beach with inlets allowing access to interesting towns and shelter. Within five miles of one another, for example, are Cape Porpoise Harbour and Kennebunkport. The former is a working harbour with lobster and fishing boats always on the move. The latter is more yachting oriented and 'tony' with its entrance 'guarded' by great American-plan hotels and estates such as that of President Geo. H.W. Bush. The two harbours and the associated towns also could not be more different.
This portion of Maine is only a little over two hours driving time from Boston so evidence of wealth and 'civilization' abounds. This is either appealing or not as the case may be. But a constant from West Quoddy Head to Kittery is lobster pots. Maine has a 12 month lobster season and pots abound. In some places it looks like one could walk ashore on the buoys. This is the 'down-side' of cruising in Maine. Avoiding lobster pots can be stressful and tiresome. That and the requirements of US Customs & Border Patrol with respect to cruising permits and the associated reporting that are much more onerous than those imposed upon US yachts cruising in Canada (a pet peeve of mine). But I digress. Despite these short-comings, Maine is a magnificent place to cruise and I encourage it whole-heartedly.