There are lots of options with lots of trade-offs.
The rational for the Bermuda route
is threefold - #1 it gives you a nice place to recover and repair after your gulf stream
crossing, #2 most folks are trying to get over to 65W before hitting the trades and Bermuda
is at 64 40W so a natural turning point (although a little further north than ideal), and #3 Bermuda for some reason does not often get destroyed by hurricanes, so it is possible to leave a bit earlier, potentially avoiding the start of the winter lows, and then sit in Bermuda until after the hurricane
season is well and fully over.
The primary rational for leaving from Norfolk/Hampton roads is that it provides the closest gulf stream
crossing, a relatively narrow gulf stream, and a turning point in the gulf stream so you can often pick eddies with favorable current
. From here you can certainly pick a decent weather
window that will get you across the stream and into warmer weather
. And if you don't have an ICW boat
(mast or draft) this is a sensible departure point.
Charleston is further south and thus typically (but not always) has less punch from lows, and has a decently close gulf stream crossing. It makes some sense if you can and want to use the intercoastal from Hampton to Charleston, but this tends to take more time than simply jumping offshore from Hampton.
The trip out from Florida
along the various islands to the Caribbean
is 1000 miles upwind. Many people find it hard going, but some like it. I think it depends on your perspective about motoring (lots of it) and what your desired time frame is for getting to the Caribbean
- 1000 miles upwind can take 30 sailing days or perhaps 3 months if you spend 2 days ashore for each day sailing
plus the couple weeks getting down the icw
- while offshore from Norfolk takes 6-10 days in total.
The historical offshore route was to head
out to 65 w at about 26N, which is usually just above where the trades start and then to head due south. But that can ge a good or bad routing depending on the specific weather pattern in place. The year, the past 2 weeks it was a generally bad routing and it was better to stay W longer. The offshore routes are a hell of a lot easier now with the various weather tools available (primarily gribs) to fine tune the routing. If thinking about this trip you owe it to yourself to learn how to get gribs and how to practically understand and use them to make routing decision offshore.
However, to balance that, you have to understand that weather forecasts are notoriously inaccurate past 48 hrs and if heading offshore to the carribean
you will likely encounter some sort of weather surprise. You simply have to be prepared for and able to deal with whatever is thrown at you. This can be uncomfortable and hard work (by any of the routes), but it is a challenge and an adventure. If you (or your crew) absolutely don't want to be uncomfortable or to work hard I would suggest you simply not do it - not by any of the routes. But if you are up for a challenge and an adventure I would suggest it could be a great moment in your life.