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NE Itinerary - Late September

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Please help with a 7-8 night trip this September. I've read quite a few posts, but there are some specific things that interest us. I know early to mid-October would be a better time for leaves, but due to schedules, the only alternative would be a trip starting no earlier than 10/17 and I think we might miss the color by then. For this trip we're looking at Boston, NH, and ME.

Places of interest:
Martha's Vineyard, Cape Cod, Nantucket
NH - Jackson, Sandwich, White Mountains (Mt. Washington)
ME - Portland, Acadia, Rockland, Camden, Kennebunkport

WIndjammer Cruise
Leaf Spotting
Lighthouses (Portland Head Light)
Whale watching
Freedom Trail
Duck Tour
Boston neighborhoods - Waterfront, North End, Beacon Hill, Back Bay, Public Garden

My initial thought was to fly in and out of Boston, but the fare isn't significantly different if we fly into Portland and out of Boston. I haven't checked how that would affect a rental car, but it would save a little time. It appears that we would be better off doing weekend nights in Boston and weekdays in smaller B&Bs.

Any thoughts on these lodging options? We prefer smaller inns and independent hotels over chains.

Boston - Charlesmark Hotel, Newbury Guest House, Harborside Inn, Clarendon Square
Maine Coast - Berry Manor Inn (Rockland), Hartstone Inn (Camden), Camden Maine Stay
White Mountains - The Inn at Thornhill, Inn at Ellis River, Darby Field Inn, Notchland Inn

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