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Beginning to think about Hudson Valley drive -- need to know some basics

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Hullo, my dears.
My SO and I are thinking about doing the Hudson Valley Drive and I need some info for a starting point. I've bookmarked a bunch of HV websites and read some threads here but nothing answers my questions so far. Hope you guys can help:

1. We can go in August. Would that be a good time?
2. We're starting in Toronto and want to end up in NYC for two or three days, then drive home. How long would we need to do this reasonably well, stopping for overnights, seeing sights, etc.
3. Would the drive home be a different route (eg different sights to see, places to stop) than the drive down?
4. We would be driving in a tiny sportscar that would have room for about two small duffel bags in the trunk. I'm not used to packing light -- will I be able to manage?

Is there anything else you think I might need to consider before starting to plan in earnest?

Thanks
gtg

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