In my experience, the wind usually lays down to some extent at night. If you're sailing or running at displacement speed (5 to 8 knots), have a late, leisurely dinner before departure. Make the crossing in the dark - there's not much to run into. Your arrival should be after sun up allowing your harbor entry with full visibility. This is important particularly going to the Bahamas as you will be able to see the coral heads entering off the beaten path anchorages.

Joe McCall's comment is really #1. I would expand that to include winds from NW to N to NE an East depending if you ate power or Sail. If Sailing and winds are 10 or less I might go with NW wind. I've cleared in at Cat Cay many times, taken deep draft vessels in with no problems in good light. Important to have a good printed Cruising Guide for all the Bahamas.

Many working people get trapped by schedule. You take the time off from work, then the weather gets questionable. It is hard to make the decision not to go when the time off from work has been set. I've been there, particularly having to get back to home because the leave from work is drawing to a close. In the end, the outcome will be much better if you choose not to make the crossing or call the boss and tell them you can't get back on time. There are always better options to forcing a bad weather voyage.

The title focuses on the Gulf Stream, but the four things to consider apply to any blue water trip and probably the Great Lakes. However, in my personal experience crossing the Gulf Stream, number five is: NEVER cross the Gulf Stream if there is currently or a near term forecast of wind over 5 or so knots from north of an imaginary line East to West anywhere along the planned route. This is because the current in the Gulf Stream, along the US East Coast up to North Carolina, is at least 50 NM wide and runs from South to North all the time with a speed of at least 2.5 knots (I have seen it greater than 5 knots). Even a steady wind of 10 knots out of the north will pile up surprisingly large waves, and as the wind blows faster, the wave period becomes progressively shorter and the waves start to break. A steady 25 knot wind out of the northwest or northeast can make the Gulf Stream very nasty. However, a 10 knot wind out the south on a sunny day is idyllic. As always, the most dangerous piece of equipment on a boat is a calendar. The distance across from Palm Beach to West End in the Abacos, is about 56 NM. The distance from Miami to Bimini is about 46 NM. Don't forget to account for the considerable drift your boat will have to deal with.

Also don't lose out on "OK" conditions waiting for "perfect" conditions. Each year I read posts about boats waiting in Florida for better weather to cross while other boats are enjoying the Bahamas. From many points in Florida it's only a long day sail across and even a bumpy ride can be fun. There often seems to be a mindset that you should only head across when everyone else leaves. Know what you, your boat, and your crew can tolerate of course, but don't wait forever!