You can readily go from Port Jeff to
Maine with just day
sails. Plenty of good places to
anchor or take a mooring/slip if that's your preference. From Port Jeff, I would go to Fisher's Island and
anchor in the east harbor. A long day gets you to the
Cape Cod Canal, where you can anchor near the entrance (I like Wings Cove) or go a little further into Onset. If that's too far for a day there are plenty of shorter options: Dutch Harbor, near
Newport is nice. Skip Cuttyhunk because 54' is too big for the inner harbor, and the outer harbor can be rough. Make sure to time the currents at
Cape Cod Canal. If you want to go up the MA coast, Scituate is a decent stop, or Warren Cove, Plymouth for
anchoring. Then Marblehead, Salem or Gloucester MA are fine, but I prefer the Manchester Yacht Club in Manchester by the Sea. Then New Castle/Portsmouth NH. York Harbor, ME is beautiful, but check if it's a little tight for your
draft. Then you're up to
Portland. Not sure you'll have time to get further up the coast with your constraints.
Get a copy of 'A Cruising Guide to the Maine Coast' by Curtis Rindlaub and Hank & Jan Taft. One of the best guides I've ever seen, and covers everything.