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All of this depends on the wind.
Shouldn't be a problem if you take the outside route. The inside route is for small power boats. The distance is roughly 105nm depending on routing. If you can figure that you'll average a very conservative 4knots with prevailing south westerlies, then it should be roughly a 26 hour sail. This is based on a very direct offshore routing, west of Giant's Tomb, west side of the Watchers, east side of North and Long Island, east of Papoose Island. Great water the whole way AS LONG AS you stay east of North and Long islands. Be advised, you could be in for some serious swells coming off of Lake Huron if we get any sort of sustained (3 days) high (15knots+) winds from the west. This would be outside the normal pattern though.
As a 2 week trip, it's more than doable. I would allow for 3 days of passage each way which would give a week with your friends.
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1978 30' Hughes Northstar 1000
1964 20' Bertram Moppie