I think this works, but would like feedback. Second week of September visiting Boston for 3 nights. Driving to Bar Harbor for 2 nights. Should we stop overnight along the way and, if so, where? It looks like a prety long drive. We will then have 2 more nights. Should we stay in Maine and fly out of Portland or head back to Boston and spend 2 nights in Cape Cod or 1 night in Cape Cod and our final night back in Boston? Obviously, the air fare is cheaper round trip to Boston. I've planned three-week trips to Europe easier than I seem to be doing with this. Thanks in advance!!!

Boston to Bar Harbor is about 5 hours if you take the freeway, no need to stop overnight on the way. From there I would head down the coast and stay wherever suits your fancy...Saturday nights in early Sept might encounter some full-up coastal places but the rest of the week should be a breeze.

Southern coast of Maine (Wells or Ogunquit) is an easy 95 min drive to Boston/Logan, so fly out of Boston if it saves big bucks...just don't choose a morning flight if you're staying on the Maine Coast the night before.

I would skip Cape Cod - too much driving. My suggestion would be Boston - Bar Harbor (no need to stop on the way) and then spend a night or 2 along Maine coast (Wells or Ogunquit area as previous poster suggested). Depending on time and day of outbound flight, might stay final night in Boston.

Portland is quite close to Boston - take the less expensive airfare - and many flights out of Portland end up requiring an additional connection for your trip.

Thanks for the reply. If we wanted to take the coast and sightsee along the way and stop overnight, what would be a good stopping point. We will probably take the freeway on the way back.

The southern coast of Maine has some beautiful towns like the Kennebunks and Oguiquit which I always think of as summer house type places. There are nice shops and great restaurants and these are popular places to weekend. Portland has a fun Old Seaport part of town but it is a city. Boothbay might be a good choice because this area of Maine is more rural with roads to explore. If you look at a map of the coast, Rt 1 is wonderful to explore from Brunswick to Ellsworth but requires driving out on some of the points such as Pemquid Point. This is slow but picturesque driving. When you leave Bar Harbor you might consider stopping in Camden for lunch - the harbor is probably the prettiest in Maine. I'm not sure when the windjammers head south. Boothbay would be a good place for restaurants and a place to stay. (This assumes freeway to Bar Harbor, taking the slow route back to Boston.) There is too much to see in Maine. The Cape has beautiful sand beaches while Maine has the rocky, craggy dramatic coastline. I would skip the Cape and spend more time in Maine.

I'd say either get an early start on that 4th day and make your way up to Maine, exiting in York to Coastal Route 1 and continuing up to Bar Harbor. Or, instead of that 3rd night in Boston, head north on that 3rd afternoon, stopping in Southern Maine for that 3rd night, maybe Ogunquit or Kennebunkport. You'll find a place that catches your eye and even beachfront should be affordable if it's not a Fri or Sat. Get there before sunset!