Our Sailing Plan - Maine to Chesapeake...Thoughts?

[Reluctantsailor]

So we spent the last to nights going over the cruising guides and charts mapping out our plan for May. We realize that weather and such may alter these plans but we are willing to be flexible. We have a month to sail from Belfast Maine to Chesapeake that being said we are not in a rush and if we only make it to New York or Boston in that month we are okay with that...we don't want to risk weather or push ourselves this is suppose to be fun...we have based our plan on sailing 30-35 NM a day sometimes more sometimes less. Our Hunter's hull speed is 6.5 and we figure we will have to motor somewhat. Does that seem reasonable?

We plan to leave Belfast first week of May (I know it will be cold but we are canadian and if we didn't sail when it was chilly we would never sail). Here is our planned stops some have more than one listed because the stop tha night would depend on the weather...any suggestions or ideas are appreciated...

Rockland, ME (not that far but we thought it will be cold so do smaller legs)
New Harbour or Pemaquid Harbour
Five Islands
Cape Elizabeth or Biddeford Pool or South Portland
Cape Porpoise or York Harbour, ME
Newburyport, MA
Salem, MA
Plymouth
Onset
South Dartmouth or Westport, MA
Newport RI or Point Judith
Fishers Island, NY or Niantic, CT
Branford, CT
Norwalk, CT
City Island or Throgs Neck
New York/New Jersey
Atlantic Highlands, NJ
Manqasquen Inlet
Atlantic City
Cape May
Delware/Chespapeake city

THen we would find a marina to haul or boat out for the summer and come back in mid October to sail the Bay and head down the ICW. But like I said if due to weather or other issues whereever we are at the end of May we will have to stop and come back later in the summer fro a week to sail her farther. Does our plan seem doable should we try to do more NM in a day or less....have we missed out on a good place to see or anchor? Thoughts?