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Barquito
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I single hand my boat some. I have a tiller pilot, but, it could fail. I understand I could heave-to in order to lower sails. What I don't understand is how the boat would stay hove-to if I lower the jib. Wouldn't the boat tack once the sail starts coming down?
 

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If the purpose is to lower your sails, I would lower the main 1st. and tidy it up. The backwinded jib and the tiller put over should keep you hove-to, while you do that.

I heave-to to reef when I'm alone. I can take my time. Makes life easy.
 

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are you trying to drop all sail? I sheet the main in tight and lock the rudder. That will keep you pointed nearly directly into the wind and barely moving. I then drop the jib and tidy it. Once that is down you can drop the main. The whole time, until you have the main almost dropped. The lashed in main will keep you nearly pointed into the wind and not moving much.
 

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Most boats will heave-to on the main only. The rudder will be pulled over hard and try to drive the nose of the boat into the wind. The main sheet will be eased a little bit. As the main sail gets some drive the boat will come up and the main sail will lose power, letting the boat fall off again.

My boat lies hove-to a little better on main only than with main and jib. It is useful to get into hove-to using the jib because having the two sails fighting slows the boat down faster. However once you are there it lays at a better angle (about 40-50 degrees off the wind) using main only.
 

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I single-hand quite a bit.

I reef when hove-to with the jib up.

If I need to drop the jib I do it either when on a run and it is blanketed by the main, or if I have a downhaul rigged it will come down when close-hauled and I don't have to leave the cockpit.

The main I drop when coming in after I get under power and head to-wind.
 

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We used to sail a Cape Dory 27, also an Alberg design similar to your Bristol 27, and hove to regularly to lower the sails. The procedure was good practice for us and I found it kept us from making a mess of things by dropping sail too quickly while trying to manage the motor.

We never tried to heave to under main or with the main, at all. We didn't have lazy jacks or any kind of main wrangling system, making lowering and flaking the main one of the primary reasons we hove to in the first place. We would generally let the main out, heave to under headsail alone, start the motor, lower and flake the main, then let the headsail out and motor in while we dropped the headsail.

The key, in my limited experience, is not to have too much momentum when you heave to. We would get close to the wind, sheet in the headsail, let out the main, then tack but leave the headsail backwinded and let the main fly out with the tiller lashed off. The boat should settle in and let you do whatever you need to do.

I found it's also helpful when you have seasick passengers, the motion is a lot more comfortable.

We also hove to so we could reef easily.

I also hove to so we could make lunch...

I'm lazy, I guess :(
 

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Dreamer -

Are you able to accomplish this w/o a tiller pilot?
Yes, I use a turn of line around the tiller tied off on either beam with enough tension to hold the tiller and still move it by hand. I have a type of tiller tamer as well but it eats line rather quickly.

With the tiller manageable I can lower sail and secure it. I'll lower a section, stop the halyard, secure sail, repeat until down. I don't worry about flaking it until I get back to dock. Then I flake it at the mast followed by the leach. I don't have lazy jacks either.

My boat is light and easily changes course by me shifting weight or a wake or a shift in breeze, so I am often making corrections with my foot.

This is what I do when coming in, it works in light air and calm water on lakes or behind a break. In heavier air, heave-to.
 
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