Help with route for road Trip, NYC, PEI, Quebec, Montreal & Chicago.
 

Not long back from an incredible Christmas/New Year driving from Dallas to Memphis, Nashville, NOL back to Dallas and points in between. It was an amazing trip and I fully intend to do a TR BUT we find ourselves returning to the US this August (late August into September). We have a function to attend in NYC and will spend 5 nights there. This will be our 4th trip so this will be about spending time with family and friends for the 5 days and eating and drinking 'like locals'. We will then have 3 and a bit weeks to go for 'a drive'. We have previously driven from Boston and up but will do the bit between NYC and Boston that we only saw on the train and some places we missed / loved previously. We would love to go as far as PEI then down to Quebec, Montreal and then Chicago for our flight home. We have been to Niagara Falls, so don't really 'need' to revisit but certainly may. As we arrive into NYC and out of Chicago we are mindful and accepting of the one way drop off fee re the rental car, but have decided that the cost is worth it to not go 'backwards'.

I'd love to hear your thoughts on routes, stops, inns, B&B's etc. We love scenic drives/ walks, local food and wine. Thanks as always.

Check the mileage. PEI is the outlier. Start with Quebec and the goe west. You might want to add Toronto to the mix. Maybe spend some time in the Thousand Islands area on your way to Toronto.

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Check rental car rules about crossing the US/Canadian border. Not too long ago I picked up a Fodorite in Burlington VT who had ferried across Lake Champlain after taking the train from Montreal south to NY (not NYC). So you could fly to Burlington, cross the lake and take train to Montreal and do a Canadian car rental. Or you could fly to Montreal from NYC. I think you have done plenty of New England traveling. The drive thru Maine into New Brunswick is kind of long and boring. PEI is wonderful to explore. If you want to visit Nova Scotia, the eastern coast is best, Cape Breton is a spectacular drive, drive across to the Bay of Fundy because it's interesting. I liked the Annapolis area. We did this trip in August and discovered things like fresh peach juice and wonderful desserts in tea rooms.

Quebec City and Montreal are wonderful. But I don't think you would enjoy the drive from PEI to Quebec City. But you have enough time.

I agree with others that getting to and back from PEI will take a lot of extra time. What is it that attracts you to this destination?
I am also not sure what you mean about having traveled before from "Boston and up."

A few thoughts.

if you want to see the area between NYC and Boston, then I would suggest you take the train from Ny to New London C T. Then rent a car or uber/Lyft and visit Mystic/Stonington CT. There is a nice maritime museum/ village there ( Mystic Seaport), and Stonington is a cute town, if it is Saturday there is a farmers market near the town dock in summer in the velvet mill the rear of the year.

Then drive/Uber to Newport, RI and visit the mansions. Head to nearby Providence and fly to your next destination. If you want to see Maine then either take fly or take the train to Portland, ME. There once was a ferry from Portland to Newfoundland or Nova Scotia,but I think that might not be running. Something to check out.

I answered on the Canada forum yesterday. I think the safest rental would be from Montreal after taking the Amtrak Adirondack from New York Penn station. I only take my own car across the border with a paper from my insurance company that says I am insured in Canada.

<<Not too long ago I picked up a Fodorite in Burlington VT who had ferried across Lake Champlain after taking the train from Montreal south to NY (not NYC). >>

you did indeed, Frosty. Twas I. And it worked great. I did have quite a long wait at Lake Champlain waiting for the ferry, but that was no hardship really. And actually the Adirondack line does go to NYC and thereafter DC. The train that tomfuller is referring to is the one i caught but in the opposite direction. One train a day, leaves NYC at 8.15 am and arrives in Montreal at 7 pm.

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I rented a car in Pittsburgh this past Fall, and returned it in Pittsburgh. I had no problems crossing the border. I had checked with the rental agency and they said that it was no problem.

Thanks for you speedy replies. I'll look into all suggestions, including rethinking PEI, we may even not decided until we're on the road. We will only book accommodation a few days out from each destination, except NYC and Chicago.