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Crossing to the Bahamas vs. 'weather'.
MAY-JUNE & Sept-October (sans tropical cyclones) are generally best.
Equinoctial (change of season due to jet stream shift) N-NW gales blow from late Oct through Nov., and again from late Feb to end of March.
The enhanced (NE at a steady 20-30kts) trade winds are found from mid Dec through March.
Summertime when the humidity is high will usually produce 'serious' thunderstorms .. which for some reason usually begin at ~4PM
*** NightOwl has already stated the 'best' time to cross the Gulf Stream - 2-3days 'before' a cold front (with an approaching high pressure zone 'behind' the cold front), and with the S-W winds that will 'retard' or 'stop' the trade winds ... typically about every 10-15 days during wintertime and about every 15-20 days in summer (and there aren't many T'storms).
Typically a slow moving high pressure cell, from the west & moving 'over' Florida will bring 'benign' conditions ... and that can happen 'anytime' during the year.
El Niņo/La Niņa can 'change' all the above.
Fall/Winter/Spring of 2015-2016 (El Niņo) had only 3-4 brief 'weather windows' of moderate to 'benign' sailing 'across' the GS from Early Nov. through the end of April.