Found the trip plan that I had drawn up. FYI I live in PA so it would be doable to drive to Portland, ME in a day...

Day 1: Halfway to Portland, ME
Day 2: Complete drive to Portland
Day 3: Sightsee in Portland, board ferry to NS
Day 4: Sightsee in Yarmouth, NS; stay in Yarmouth.
Day 5: Lunenburg, NS
Day 6: Halifax
Day 7: Open (en route to Cape Breton)
Day 8: Cape Breton Island & Cabot Trail
Day 9: Wolfville?
Day 10: Yarmouth?
Day 11: CAT Ferry to Bar Harbor, ME.
Day 12: Bar Harbor or Camden, ME
Day 13: Bar Harbor or Camden or Boothbay
Day 14: Halfway Home
Day 15: Home