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Autopilot as second crew member
I singlehand my 42-footer in the Caribbean and consider my below-decks autopilot my second crew member. Yes, it's an energy hog, but a wind vane will not work if there's no wind. You need to be able to trust your autopilot not only to go on deck to handle sails but also to be able to go below to use the head, fix a sandwich, sleep on long passages, etc. I use the autotack feature all the time, but to be honest, I try to plan my passages to minimize the need to tack at all.
Roller furling headsails are a necessity in my opinion, and your plan to use a Gale Sail which hanks on over the furled headsail is a good idea. The question of furling main or slab-reefing is a purely personal decision. I personally elected to go with slab reefing with a single line so I don't have to leave the cockpit to reef.
Other things to consider: Can you get the dinghy on deck by yourself? Do you have a way to hoist the outboard to attach it to the stern rail? Can you use the radio without leaving the helm? A remote command mic or handheld VHF should be on your equipment list. And be sure to wear a harness and use the tether whenever you are out of the cabin. If you go off the boat, even if tethered to the boat, you probably won't be able to get back aboard. Wear a knife on your harness.
For more discussion about safety while singlehanding, check out The Great Lakes Singlehanded Society - Home Page
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Last edited by aerie; 01-06-2010 at 04:40 PM.