I am sailing from Michigan to Puerto Rico this fall and I am too tall to go the ICW below Norfolk. I plan to come out the NY harbor about mid Oct and get down as far as time allows me before returning home for a month. I hope to make Virginia Beach.I plan to be back at the boat Nov 25. I do not wish to sail accross, but through the Bahamas. Looking for best jumping point and info about outside Cape Hatteras.
If you're too tall for the ICW you are probably not going to have a good time in Virginia Beach. I stage in Little Creek, usually Vinings Landing Marina (walking distance to grocery, West Marine, close to Norfolk International Airport).
It's three or four days from Little Creek to Abaco. What is your Admiral's objection? If you're heading to PR
don't give up Easting too readily. The further North you can get East the happier you will be.
Heading South inside the Gulf Stream takes time and attention. There will be sections at Hatteras and into Florida where you will have foul current. From Little Creek if you cross the GS at 135T to 68dW (ish) you can be in PR
in 10 or 12 days.
That time of year, you'll want to choose your rounding of Hatteras carefully.
There's considerable risk to this route, and some like Don Street will insist that one should never round Hatteras inside of the Stream... I disagree with him there, I think leaving from the Chesapeake and running down the beach is an acceptable risk if you're patient enough to wait for the right weather...
I know that Jon, like me, has made this rounding many times. I suspect he has done it more than me. It simply isn't a big deal. You can see the fronts coming down from the Great Lakes. There aren't many surprises there. From Little Creek to clear of Hatteras is less than a day on most boats. You'll have lots of good weather data available before leaving. Even if the conditions are poor you won't have to wait for more than a couple of days for it to clear unless something really ugly is happening, which is relatively rare.
More information about the familial restrictions you are working under would help us give you more useful ideas.