Hey there. I'm a
power guy, but watch the wind carefully.
I've noticed that approaching cold fronts provide the best opportunity to have a smooth
passage. This is only true if the front is fairly well spent by the time it gets to
Miami. A strong cold front will blow through quickly and provide a strong north wind before finishing the crossing.
A strong front is one that remains on a line relatively north and south or NE to SW. Often, fronts get horizontal in mid
Florida, die, and reverse themselves into an air mass of humid stagnant air. A sailboat may have to
motor in that.
So, waiting for a day after an East wind makes sense depending on the strength of the next front. I think if you see a weak front, it's better to wait more to get the wind veering from the west and maybe NW, so you can sail well.
You probably know about No Name harbor on the southern tip of Key Biscayne. Most sailboats hang out there for a short trip to Bimini and you will do OK to go when the bulk of them also go.
I don't enjoy Bimini much. It's a long way to the Berrys, which are great!
I go from
Lake Worth inlet to West End. The Abacos were great, but were now hit hard by Dorian. My last trip was with a friend in a sailboat that went about 6 kts. We hit some
weather, but it was very doable.