Hmm, thanks for the input. Regarding the toll for the bridge - I'm fine paying the toll to visit another province - although the toll is steep enough I think I want to spend a little more time there than the few hours the previous itinerary had. I understand that Sydney and Moncton aren't really for tourists, I was just planning on spending the nights there as convenient in-between points to split up the driving (also in the case of Sydney vs small town, it's hard to beat free as I have points lying around that I wouldn't otherwise have a use for). That said, if you've never been to the region and you don't know when you would be able to return, you would really drop PEI and NB entirely to focus on Nova Scotia? I mean that certainly appeals from a less-driving POV. We love exploring different foods - does that change anything in terms of where we should be visiting?

How about this:

Day 1: travel, arrive in Halifax (YHZ) late night.
Night 1: Halifax
Day 2: Halifax area (Citadel, pier 21)
Night 2: Halifax
Day 3: Nova Scotia (Peggy's Cove/Burntcoat head/Grand Pre)
Night 3: Halifax
Day 4: Nova Scotia (Halifax -> Sydney)
Night 4: Sydney
Day 5: Nova Scotia (Cabot Trail/Cape Breton)
Night 5: Sydney
Day 6: PEI (Cape Breton -> Pictou -> Charlottetown)
Night 6: Charlottetown
Day 7: New Brunswick (Shediac, Hopewell Cape, St. Martins, Saint John, maybe Saint George depending on time and how we're feeling)
Night 7: Saint John
Day 8: New Brunswick (ideally hit the Bay of Fundy locations at a different time of day to see the tide)
Night 8: Moncton
Day 9: Moncton -> Sackville -> Fort Beausejour -> Burntcoat Head -> Dartmouth
Night 9: Dartmouth
Day 10: travel, depart YHZ in the morning