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Cheap...I would leave NYC by 10/1 as the weather starts getting rough and the temps pretty cold offshore after that. You want to be in the Chesapeake by around 10/15. NYC to Chesapeake is a minimum of 5 days...weather permitting.
We left the Chesapeake one year on 11/15 and froze our butts off for 2 weeks...so it can be done but I do not recommend it especially w/ kids.
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