Of course it’s best not to sail at or close by the lee-too easy for things to go wrong. If you are sailing deep and slow (usually coming back in to the channel) have your crew press the boom out acting as a preventer. Make sure everyone is aware that keeping the boat flat is paramount to anything else.
Best to sail high (not deep downwind) to keep the boat moving as fast as you are comfortable with as the jibes will be much easier the faster you are going. When we are coming back in and there is breeze-we like to jibe back and forth with the main farily taught as you enter the jibe but as soon as it goes slack when crossing center line, you let out a lot of main sheet (have the crew grab the vang and throw the boom across as you jibe-it lets you know when the boom is crossing rather than waiting for it) and when the boom crosses, be prepared to drive down deep and then back up-kind of an “S” turn as you jibe. This lets the boom get across, keeps the boat flat and then lets you head up as you sheet in.
This is probably the toughest maneuver to get right-it’s a serious timing and feel thing. Good thing to practice outside away from everything. The faster you are going when starting to jibe the better. If for some reason the boat slows down, stop the jibe, head back up and get some speed on.
We always opined that it was much easier with the kite up, even if you are not flying it perfectly or at all.
Try this on a northerly: Sail a little farther up the golden gardens beach. Do one last spinnaker set on starboard like you always do (or jibe set) sail for a bit, jibe early for the trailer parking lot, sail all the way to the parking lot, nail that last jibe and run down the channel deep and crouched in. If you can't get all the way down the channel, you have to heat up a bit and jibe again.
If you have to sail with two sails, I think I would have been running deep, with the main mostly out (do you have a stopper knot in your mainsheet?, more people should). If you have to jibe, you must heat the boat up a bit and have the crew throw the boom over mid jibe.
That channel is very difficult.
Like Alan said, everyone has been on the breakwater regardless of their skill level. Bundy was just there last year. Brian and I have been there numerous times, and although we are getting better at running the channel, I am sure we will be there again sometime.
There were many times earlier on when Brian and I were seriously considering short tacking up the inside from the south entrance. That would be harder with more opportunity for capsize as coming in from the north (assuming you are already wet and tired). Just too many short tacks in traffic.
Alan gave us that same advice several years ago. Frankly, unless the wind is light, Brian and I have not had the nerve to try sailing in with the chute up even though it makes perfect sense. Maybe we will start trying it more. Other than that, we do pretty much what Alan says... sail high enough from the end of the breakwater on port that will allow us to put in one gybe east of the fishing pier... well to windward of the fishing pier so your next line puts you inside the channel.
This gybe puts you on starboard clearing the fishing pier sailing slightly deep, but not directly down wind. At this point we concentrate on keeping our speed up and are on heightened alert, ready to do anything to keep the boat upright. For you, that means steering as if you have the chute up... ie heading down if you start to heel to leeward and heading up for the opposite. These will be very small and very quick corrections. Do not be afraid to sail fast... fast is safer. Power boats will get out of your way, but you notify them to please stay clear.
Did I mention that you need to keep your speed up, sailing slightly deep? You may or may not be close to the breakwater at this point.
When it is windy, gybe onto port every time you get more than 1/4 the channel width from the breakwater. My philosophy is that if you gybe too close to the dock there will be quick assistance (of course you want your mast to clear the dock when you flip... cheaper that way). As you get deeper into the channel it seems that you can also sail a bit deeper since the wind has a tendency to lighten up as you go in.
By the way, your crew should help you keep an eye over the stern for puffs as you get deeper into the channel... always nice to know. At some point, after a couple gybes, you should be able to make your last gybe onto port, take a deep breath and aim for somewhere close to the I-14 dock.
It does get easier (and more automatic) the more you do it. While you are out on the sound, practice a bunch of high speed gybes. After Brian and I got the hang of that, things got easier coming into the dock.
Have fun and do not sweat the crashes!