Caribbean - tips and hints

[RickG]

September is the stinking hot month in the Caribbean. The tradewinds lay down and you can get a lot of southern component. The rest of the year is nice. A sun shade definitely helps during the height of the sun. Definitely looking forward to getting back on the boat and the PR/Virgin Islands this month.

Cheers, RickG

[chesapeakesailor]

Hi Everyone - looking to make a trip from Annapolis to St Thomas. Most folks doing the same are leaving early November but my schedule really only allows for a late January or early February departure. Some high level questions:

1) If there is a more specific thread for this topic on weather planning going down to Caribbean please point me to it? Thanks
2) What is the best place to find weather pattern data to compare a November voyage to a February voyage?
3) What is the consensus on best place to cross the Gulf Stream? Most seem to agree Cape Hatteras area...
4) How East to go before turning South if the generic prevailing wind and ocean conditions for those two months occur?
5) Any other major considerations I should think about regarding weather.

I will be on a 54 so more comfortable than a 33.

Thanks!