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However running with the front may be another story.
MY experience is with long distance open water racing in small boats (dingies).
Nothing in my experience is so far showing that big boats are any different, except that they are harder to sail :)
Gulf Stream is another story and it is another consideration. I wouldn’t go into any “stream” if weather runs against it regardless of the size of the boat unless I have no choice.
In ideal conditions, depending on a center of the front (we are talking about big weather fronts, such as nor-ester) wind will build up and seas will build up then wind gradually shifts clockwise (We are talking about eastern US). In my experience, very limited, mind you, seas will shift accordingly to wind. And subside quite fast afterwards.
It is possible to run with the front, if front moving in the same direction and with about same speed. Normally fronts are faster; however there are two-three days until front overtakes you.
In fast boat it is quite possible to overrun a front. You get into some lumpy seas with wind suddenly dying or shifting ahead. Then you get a hit with the front again and again.
Again, with my limited experience, if you continue to move and front overtakes you, and front is moving in the same direction, seas are getting beneath quite fast. If you run ahead of it, or your direction and front’s direction are on splitting course, then seas may get confusing for quite a while.
Now, I hope I provoked someone with a real experience to weight in. :D
 
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