Mark Matthews responds:
There are all sorts of sailing styles, for all sorts of people and all sorts of vessels, and, like so many other things in the sport of sailing, opinions abound on the one right way to do something. When it comes to raising and lowering the mainsail, there are a multiple of factors to consider. Are you leaving from a mooring, a slip, or a dock? Is the wind light, strong, or in between? Is the current a factor? How about traffic from other boats? Also, do you have a standard mainsail setup, or are you using one that furls on the boom or furls into the mast?
Typically, if your boat has an auxiliary engine, you get off the dock or mooring with the mainsail still stowed in its non-sailing position, yet ready to deploy (with the sail cover removed). Then you can use the engine to motor into the wind keeping minimal way on for steerage. Once the boat is heading into the wind, you can raise the mainsail by attaching the main halyard securely to the headboard of the mainsail; releasing the tension on the mainsheet, the cunningham, and the boom vang, and then taking another look up to see that the halyard isn't twisted around anything, you're basically ready to hoist. Essentially you want to keep all the tension off the sail (except that exerted by the halyard) until the sail is hoisted, then you can apply the outhaul, cunningham, vang, and backstay.
One caution about hoisting the sail: it should all be done carefully so that in the event something snags, you'll have the chance to keep damage to a minimum. If you find yourself cranking and cranking on the winch to get the sail up, something is wrong—stop or you could cause serious damage to the sail, the halyard, or one of the fittings. You might also run the risk of getting the sail stuck halfway up, which is a situation that can lead to disaster.
If you've been able to keep your boat headed into the wind long enough, you'll get the mainsail all the way up. Once the mainsail is up and the halyard is sufficiently tensioned, you have the option of falling off the wind or getting the headsail hoisted while the boat remains into the wind. The headsail should go up in a similar fashion. If you're dealing with a roller-furling headsail, many sailmakers suggest loosening the halyard tension while the boat not being used. This prolongs the life and shape of the sail. If this is the case, you'll need to retension the halyard to suit the given conditions, preferrably after you unroll it. (Remember, if the backstay is over tightened, it can some times be difficult for the upper furler to rotate, so ease a little backstay tension if the one on your boat is adjustable.)
As far as taming the mainsail goes, many sailors find that lazy jacks or a similar system are an effective way to keep the sail under control when raising, lowering, or reefing.
If you have auxiliary sails, like a mizzen, you can hoist that after hoisting the headsail. You may also want to take a look at the articles in our Learning to Sail section for more information.
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