How late can I head down to the Chesapeake

[Muaddib1116]

I've been planning to go south to the Carribbean this year. My plan has been to Jump from Newport down to Bermuda at the very beginning of November, then Bermuda to the Carribbean. For a variety of reasons, I'm considering hopping down the coast to and then working East. I would go through Long Island Sound, through New York City, down the New Jersey coast and then up through the C&D canal. I'm just curious, is it feasible to start that trip at the end of October/beginning of November?

[Benz]

Sure, people start this trip into the beginning of December. It just gets colder and colder. November still carries the risk of tropical systems, especially as you go south.
Insurance companies as a whole don't like anyone going south of Cape Hatteras before Nov 1, so there's a pileup of boats in Hampton and Norfolk waiting to jump to the Bahamas shortly after. Early November is the traditional big yacht exodus from Newport, so your timeline is right when lots of folk are doing it.

[maine50]

The Salty Dawg rally to Antigua & also Bahamas ( 100 plus boats usually) start after Nov 1 so lots of boat movements from New England the last 2 weeks of Oct. We left Stamford (western Long Island sound) and motored directly (Via East River) to Bay Bridge tunnel/bridge (Hampton Roads)in 48 hrs. With a 50ft boat you should be fine just watch the weather closely and allow extra time so you can pick your transit days. If you skip D & C canal route and go directly to
lower Chesapeake you can save yourself days assuming you have a crew so you can do overnights.