Hi and thanks for asking.
I have made the trip a bunch of times on a variety of yachts. Of course, those were all before the
current health crisis.
First consideration is air
draft and
water draft. Over 65 ft airdraft is out of the question for any
interior transit.
Water draft over 6 is difficult though I know that 7 ft can make it carefully.
Currents from NY to Norfolk, VA are favorable but weak. South of Hatteras, along the near shore, the
current may run south as a counter current in many places. I have found it a bit random. Getting onto the shallow continental shelf makes for a very bumpy ride with the choppy seas.
Bucking the
Gulf Stream is horribly slow. Some times
boats will sail out to the other side of the Stream and enter the
USA via a
Bahamas transit, really the long way around!
If you can do it:
NYC to Norfolk, a couple days of straight sailing.
Norfolk to
Beaufort, NC inside, about 5 days and very pleasant.
Beaufort to
Florida with stops in Charleston, SC or Jax or Cape Canaveral if you feel the need to stop. Easy in/out is a major factor in picking a layover. Probably 7 days of sailing plus layover time.
I use
www.ventusky.com to plan my
weather windows. There are plenty of other sites, too. You are looking for a NW
wind. A NE
wind is likely to be stormy and very uncomfortable though fast.
Norm
Averisera