Winter months you have a good chance of hitting a cold front with strong winds that, if you're in the Gulf Stream
, will be opposing the direction of the currents and result in big, steep, nasty waves. Risk increases the closer you get to FL
Summer to fall you enter hurricane
season. Careful attention to forecasts and a bailout plan can usually deal with that but better to avoid if you can.
So, best times to go; fall when hurricane
risks decrease but before winter fronts increase OR late spring after fronts decrease but before hurricane risks increase.
Other than the above mentioned weather
issues you will be in the trade
winds with a downwind run all the way. You will also have a current
with you most of the way. How much depends on the route
So final answer, the best weather conditions are when you have no conditions IE normal trade