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Boston-PEI-Quebec (or Montreal) drive

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We are flying from Texas to either Boston or Portland, and then driving to PEI for a few days then to either Montreal or Quebec for a few days and then back to Boston. We had never been in that area so do not know the best kinds of transportation or actual driving times when you account for traffic and slow, windy roads. We would like to stop somewhere along the New England on our way up. I have been doing research but it can be very confusing especially about taking a ferry or a train. So:
1) Boston or Portland?
2) What seaside town would you choose if scenery and a lobster roll are very important? and scary roads are to be avoided.
3) Are there any trains that would be efficient?
4) What about ferries?
5) Montreal or Quebec? or possibly both?
thank you, p

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