On the second day of the Steeplechase the racers can either follow the Intracoastal Waterway or take short cuts across mangrove patches or mudflats (thus the name Steeplechase where in Merry Ole England the race was from the start line to the Steeple that was visible above the trees -- any route that you wanted to take, be it over fences, bushes, through creeks, or whatever).

However, for the Key Largo Steeplechase, there is still two obstacles that must be addressed and there are two options:
1) Sail deeper into the Bay and more westerly and then go through a narrow creek in the mangroves called the Bogies. Out of the past 18 years, twice this route was used to take a victory. It is very narrow (about 4 boat widths wide) and if the current and wind are against you, you are doomed. No room to tack or anything. Paddling is the only answer, but not a very good one.
2) The Intracoastal has two magrove creeks to navigate to get to the wide open waters of Blackwater Sound and the last 4 miles to the finish line. The first creek is not too long and not bad to navigate, but Dusenberry Creek is quite long.
No matter which way the wind is blowing when you enter Dusenberry the wind is on the nose all the way through the creek. And the current is also usually against you.
Now, the creek is about 50 or 60 feet wide which allows you to tack up the channel. But how you do this is pretty important.
First, the current in the middle of the creek is much stronger than the current at the side of the creek (where there is much friction and often even some eddies that will help you upstream a bit. So, this tells you that you want to stay near the sides of the creek as much as possible.
Next you need to know about the "Rule of 90" where wind likes to cross a land-water area at 90 degrees. Howevever, with this small an area, it will not make it, but it still will try to head into the mangroves at some degree.
This means that if you can stay near the sides of the channel you will get a lift from the wind (albeit you will certainly have to pinch to stay there) and you will have a much slower current against you.
So, the secret is to rush across the middle with full speed and when you reach the other bank sheet in hard and pinch along the bank.

I have passed this little gem along to most of the sailors in the race, but most seem to forget about it. I even use this in my seminars when we are discussing wind and currents.
Also, I only raced the Ruff Rider once, but used this technique on the start of the second day and won the race. So, it works.

Good luck,
Rick