I've got one-day conference in Boston the first Tuesday in June. I've never spent any time in New England outside of a couple trips to Boston and Martha's Vineyard, so I'm thinking of flying into Logan on Saturday, and then spending Sunday and Monday heading up the coast in Maine.
Since I've never been in that area, and know very little about it except for some basic geography, so I'm interested in ideas and suggestions that would match well with such an abbreviated itinerary. Interesting locales or towns, points of interest, etc.
Some thoughts follow, keeping your time constraints clearly in mind. I wouldn't recommend spending time in weekend traffic
anywhere on U.S. Route 1 except where necessary or interesting (largely, IMnsHO, only once past Brunswick).
I-95 north, get off the highway at York (exit 7? not certain). The Route 1A "loop" is a short but pretty drive; stop and see Nubble Light (Cape Neddick). Pick up US 1 again at the 1A / 1 merge at Cape Neddick and continue NE to Ogunquit via Route 1. Stop in Ogunquit, where there is a shorefront paved walking path called
The Marginal Way. One mile long, runs along and above the rocky shoreline; worthwhile. Lunch in Ogunquit, walk the broad beach there for a bit if so inclined. Leaving Ogunquit I would take Route 1 north
only as far as Wells; use 9/109 west to get back on I-95 and proceed to Portland via I-95 to your presumably pre-arranged lodging. That pretty much eats up your Sunday right there.
Portland has changed a lot in recent years. It has become very much "gentrified". Locals / natives displaced "outward" by wildly escalated property and housing costs in Portland often (and not in jest, I assure you) now call it "Portlyn", a sarcastic hybridization of Portland / Brooklyn (...you get the picture from whence a great many of the newcomers originate).
There is a harbor tour in Portland that's interesting, providing some narration of history and future waterfront plans, seeing a fair amount of the area from the water (weather permitting, of course). That would consume much less time than a sail. Fwiw, I grew up on the water but still enjoyed that harbor tour. I frankly don't find much in Portland to be of any particular interest to me, although "upscale shopping opportunities" certainly now abound. There are numerous decent restaurants in Portland. Or, after your overnight in Portlyn, you could check out, then drive to Freeport (LL Bean), Brunswick (Bowdoin College) or Bath (Maritime Musuem). The Botanical Gardens at Boothbay are also beautiful. I wouldn't range further afield than that, since you will presumably need to travel back to Boston on Monday. You'd obviously have to pick and choose among the assorted time consuming ME itinerary options. So many choices and places, so little time.
Just some random (alleged) thoughts and ideas; hope some of it helps.