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About getting out of a leeward slip, first, Jay Fitzgerald's book covers this. It's best to head out when one knows there's a calm. If it's 5 am with signs of the wind picking up later, then do it at 5 am. It helps to learn a lot about the weather and all the ways to forecast it for the given area and pricerange.
I've been in this situation on an engineless C&C 27, as a part of Sail Transport Company, which was in the works in Puget Sound a few years ago. The boat's flipped around in the early morning before the wind picks up so the bow faces out. This helps with someone on tiller as one or two on the dock bobsled her out of the slip by the stanchions and pull on the bow and stern with a couple lines, with each line around a dock cleat in the process. There was like a 15 knot southerly in the main channel of Puget Sound, and the slip opened to the south in Shilshole Bay Marina. The mainsail was set, but I don't remember how reefed it was. There was a self-casting line secured to the port bow cleat that looped around the cleat at the end of the dock across the channel between docks in the marina, so like 50 feet one way, 100 ft loop. In between puffs, one would haul that bow line as the other was on main and tiller, didn't take much muscle or a winch or handy billy, and when the bow was far enough out for the main to drive her forward in time, the casting line did it's job, and I think the loop was then pulled the other way. I guess this would really depend on the friction and shape of the cleat or piling, the angle of the loop, and the friction of the line. I don't remember if she had that yuloh sculling oar on her yet.
Last edited by limpyweta; 04-15-2013 at 08:12 PM.