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Montreal and Quebec City in August

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We'd like to plan a trip to Montreal, Quebec City and some destinations between/nearby. We had hoped to go in September, but we have some conflicts then, so August is more available. Several questions to help me get started.
1) Does it matter when in August? We're pretty flexible for the month, is earlier or later better, weather-wise, crowds-wise etc.
2) I originally thought we'd fly into Montreal, stay 3 or 4 days, get a rental car, do some touring, go to Quebec City, drop off the car, and then fly home from there. But it seems that flights from Quebec City to Washington DC go first to Montreal. Is it better to go to Montreal, train to Quebec City, THEN rent a car and make our way back to Montreal and then fly home?

I'm sure I'll have itinerary questions when I get these basics covered, but this will help me get started!

Thanks, as always,
Alice

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