I guess it all depends on what your goals are... Ottawa, Montreal, and Quebec are all great cities, so barely spending a day in each seems a tad rushed, but then again I read once of a traveler who had breakfast in Bratislava, lunch in Budapest, and dinner in Belgrade, which sounded wonderful to me-- so if that's more the kind of experience you're after, it could be a blast. In that case, my only advice is to play lots of good music loudly in the car!

I would highly recommend not skipping the Cabot Trail. I did the trail back in 2022 and it was one of my most memorable trips, an incredibly scenic drive with tons of great hiking and sightseeing opportunities. The people in Nova Scotia are also incredible.

Ur not missing much in Nova Scotia

Be sure to investigate the one way dropoff charge from Chicago to New York and also the insurance, etc. for the Canadian portion.

I love a road trip. Have a great time.

Then that's what you should do. You're really giving little time to both Chicago and NYC, both amazing cities and you could easily spend a week in each. Ditto Boston, which is much, much more than the Freedom Trail. Personally, I'd limit my Canadian and US travel to one region in each, aka, British Columbia and Alaska plus Washington, Oregon and - maybe - Northern California or Canadian Maritimes plus Quebec (you can skip Ontario for this trip) plus New England and NYC. That would give you much more quality time in each and give you a true flavor each region. I'm biased because I live New England, but I feel that international travelers often have no idea how rich in history and culture New England is (not just Boston). YMMV, but that's my suggestion.

They usually have concrete barriers, at least as far as I can recall the 99 does. I've driven most highways in Southern BC and from your itinerary really only that stretch between Pemberton and Lillooet on the 99 is one I'd describe as "difficult", but doable. Some people don't like the road between Revelstoke and Golden, but for me this one is fine. Just that the roads here are not like the freeways in the US or highways in western Europe. I guess basically most of our highways are single lane a lot of the way, with hair pin turns and switchbacks, steep grades over mountain passes. If you are ok with those types of roads you should be fine. They are all in decent shape.

I think if you wanted to fill some time and didn’t mind a pretty considerable drive then driving up the St. Lawrence River from Quebec City to Edmundston (which is BEAUTIFUL - and I’m pretty confident something not many Canadians even know that) and then looping down past Fredericton to Sussex to Alma (you take highway 114 past Sussex - it’s a slower road but the view of the bay is incredible) is something you could pack into a day - but it will be a long day.

Fredericton and Saint John are missable for sure - there’s nothing significant to see in either place (Saint John has a site called Reversing Falls but it’s nothing interesting at all unless you want to stand there all day and watch the tides reverse direction and even then……).

From Alma, depending on what you want to do, you could get a parks pass for a day or two which is $10/day and lets you hike some trails in Fundy National Park (Third Vault Falls is always a pleaser). I’d recommend going to the Holy Whale brewery in Alma, if that’s your thing.

From Alma, you have a good base to either camp or grab a motel on the water for a night and then head out the next day to Hopewell Rocks (this is the classical “Bay of Fundy” location). There is an entrance fee to get down to the rocks of $18 dollars. In my opinion worth the price of entry - MAKE SURE YOU GO AT LOW TIDE IF YOU CAN ONLY PICK ONE TIME TO GO (they have a tidal calendar on the Parks NB website which shows when the tides are high and low). The tides cycle every 4-6 hours - if you have time to kill coming back and seeing the opposite tides can show you how dramatic the change is, but if you don’t want to wait that long I’d recommend low tide only as the site is much more dramatic - wear shoes you don’t mind getting muddy.

After Hopewell rocks you can do a 180 and start your drive back to the Maine border. There’s nothing interesting to see up towards Moncton unless you want to go as far as Shediac.

If you have the time, a stop in St. Martin’s to see the sea caves and potentially a small portion of the Fundy Trail Parkway is a good thought (essentially the opposite side of Fundy National park from where you were but this part is privately owned - good views up to Salmon River which has a cute little suspension bridge over a river with a spectacular view but is a bit out of the way).

Again, Saint John is missable, don’t bother getting off the highway. If you want a scenic drive along the Kennebecasis River then take Gondola Point Arterial road off the Highway to Gondola Point road and drive it until it links back up the highway before continuing to Calais.

This all could be jammed into 2 horrible days or 3 more reasonable days:

Day 1: Quebec City through Edmundston to Alma (big driving day) Day 2: Hike the trails in Fundy National Park and see Hopewell rocks (more relaxing) Day 3: Drive to St. Martin’s and explore for a bit then hit the highway to Calais, Maine (gives lots of leeway depending on how early you want to get to Maine - the border crossing is usually deserted AND YOU GAIN AN HOUR CROSSING INTO MAINE FROM NEW BRUNSWICK)

I think this gives you much better scenic options without stretching yourself too thin. While it’s my great pain to say skip Nova Scotia for this trip - I think it’s in your best interest.

DM me if you want more details. I loved every minute of the East Coast.