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Need help with Hudson River Valley itinerary

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I'd love some help with a preliminary itinerary to the Hudson River Valley. I'd like to spend 6 nights and need advice on how best to arrive, where to rent a car, and how to pace the trip. We're from Austin, TX, so am wondering if I should just fly to LaGuardia and rent a car, or if its better to take a train from NYC to a stop in the lower valley, rent a car and proceed. We'd like to tour FDR site, eat at CIA if possible, eat well, see some art, visit a winery, maybe see a play, really, just enjoy a "best of" the valley trip. I'd like to spend a couple of nights in Rhinebeck, but am not sure where else to sleep. I've read some other posts and there seems to be alot of worthy stops. Any ideas on pacing/transportation/priorities welcomed.

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