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Asleep at the wheel
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Welcome aboard! Do you have alternative propulsion (either an engine/motor or paddles/oars)? If so, having someone aboard is less of an issue on a boat that size.

For your first day, pick a day when there is essentially no wind. Go out a bit and drop the anchor (if you don't have a dock). Practice lashing the tiller in the middle of the boat and deploying and retrieving the main sail (the one on the boom). Don't worry about the jib (the foresail, or the sail at the front). For this you'll need to know what the halyard is and where it is on the mast, and where the topping lift is (if the boat has one). Be sure to release the main sheet (the thing that controls the angle of the boom) before you raise the sail. If there is any wind, make sure that you are upwind of the boom. Then push the boom out to one side (or let the wind catch it) and play with the main sheet. Learn how to cleat it off and how to uncleat it quickly. Haul in the anchor, get back to the dock or onto your trailer. If you manage all of that without doing any damage to your boat, yourself, or the other boats in the area, it was a great day. Go celebrate.

The next time, pick a calm day (2-5 knots). Repeat the process above. Note carefully that hoisting the main at the dock can pose problems when there is wind. Get away from the dock, and point the bow into the wind before you raise the sail. Remember to release the main sheet, too, or the boat will heel as you raise the sail. If you feel it leaning a lot, you forgot. Release the sheet and finish raising the sail. Practice sailing across the wind, being sure to tack (i.e, turn the bow into the wind, and you can start this by pushing the tiller over hard so it points at the same side of the boat as the sail). You may make a bit of leeway (i.e., get blown downwind from your starting point) as part of this, but it will keep you in the vicinity of the dock/ramp in the event you have problems. Point the boat back into the wind, lash the tiller, drop the main sail, and head back. If you have accomplished all of this without harming your boat, yourself, or anyone else's boat (or anyone else), then it was a great day; go celebrate!
 

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Asleep at the wheel
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3,016 Posts
Desert, I hope it is useful. For the record, I've only been sailing 2 years. Don't take anything I say as gospel! :)

Is your boat in the water? Is it already rigged (i.e., the mast is up)? Will you be keeping her in the water or on a trailer? Is the jib (also called the foresail or head sail) a roller furling (i.e., it wraps around itself or one of the stays/wires that holds up the mast) or is it a hank-on jib (meaning you put it on and take it off every time you use it)? You'd know if it is a roller furling jib because there is a drum-shaped device about the size of a small cottage-cheese container near the bow. The sail will likely also have an edge made out of a sacrificial material like Sunbrella, rather than being all sailcloth.

The reason I ask is that I find it easier some times to fly the jib than to fly the main. I have a roller on my Allmand's jib, and will have one on the Albacore if I can ever get the time to work on her. The roller makes it easy to put the jib away, because it "just" rolls up. You don't have to worry about flaking the sail, tying it down, etc.
 

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Asleep at the wheel
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3,016 Posts
Good luck! Smart to take it slow, learn how to back up the trailer. Have you tried stepping the mast and rigging everything? You can do a lot of what I suggested, except actually raising the sails, while the boat is on the trailer. You can also figure out how the mainsail fits in the boom, check out the mast tracks and envision how the bolt rope or slugs will go up the mast, etc., in the driveway. Just don't try to raise either of the sails in the driveway.
 

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Asleep at the wheel
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3,016 Posts
Depending on the winds, the oversized sail may be needed (I assume it's a 150 or some other form of genoa, which is basically an oversized jib), but for now you may be more comfortable with the smaller sail simply because if you damage it you know you have a decent back-up sail. Not that I expect you to damage the sail.
 
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