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

I'm not aware of any travelworthy food options you would find in NB or PEI but not in NS.

Allow half a day at Pier 21 i.e. its that good. If you have any family ties, I suggest visiting the archives on the main floor. I did and found my mother & two sisters on a boat from England to Sain John, NB in 1948.

I'd skip New Brunswick (really - it's just alot of trees) and throw in another day on PEI. The Delta Prince Edward is right on the waterfront and within walking distance of lots of restaurants & entertainment. I'd also vote for taking the ferry from NS, it's a nice break and the drive from Wood Islands to Charlottetown is quite scenic. You can also stop for a walk on the Basin Head Beach along the way (the "singing sands" referred to by another poster).

For me, the real "flyover country" is not places like Nebraska or Wyoming, but rather Newfoundland, Nova Scotia and Prince Edward Island, as I have come within 7 miles of each of those provinces, but have never been on the ground in any of them. Come September 5, I am remedying that. I've taking 9 days to travel from St. John's NL to Cleveland OH by surface transportation.

I fly to YYT on September 5 and will stay there two nights. On September 7, I am setting out for Cleveland, taking the 13+ hour DRL bus ride to Port au Basques. I am booked on the overnight Marine Atlantic ferry to North Sydney, NS; upon arriving there I am taking the 0835 Maritime Bus service to Halifax. I'm just going to spend one night there, and then take a bus at noon on Saturday 9/9 to Charlottetown. I'm going to spend 4 days on PEI, and then on Wednesday 9/13 I'm going to bus down to Amherst NS to meet up with VIA Rail's Ocean train (I have a sleeper cabin booked). This train only runs 3 days per week. At Montreal, I'm booked to connect with Amtrak's Adirondack train, alighting at Schenectady, NY, where I have a scheduled 56 minute layover to connect to the Amtrak Lake Shore Limited, which reaches Cleveland at about 0353 on Friday 9/15.

Interestingly, were I to stay on the Lake Shore Limited to Chicago (where it terminates), one more train connection would get me to either Los Angeles or the San Francisco Bay Area, or either Seattle or Portland (one train, the Empire Builder, splits at Spokane and serves both big cities in the PNW).

When I get to PEI I will have visited all 50 US states and 10 Canadian provinces plus Yukon.

I can't wait.