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Single handing a sailboat is somewhat or maybe a lot related to size. Very large boats usually even electric everything, AP furling sails and so on... Equipped as such... size may not matter much for single handing.

The less than long LOA boats when equipped with all the "assists".. furling sails, reefing lines led aft, self sailing winches,
line stoppers, powered winch for halyard, windlass, AP and so on can be easily single handed... As you drop away these feature to a more "manually" controlled boat single handing becomes more of a challenge and may be almost impossible.

The short length boats are usually not suited to all the power assisted devices... skipper has to do more and more by him or herself... like steer to the eye of the wind to raise and lower sails.


If the boat is large enough to have the power devices.... then it can be single handed. Once underway in stable conditions... all one does is hold the course with the helm
 

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if you plan on keeping the boat, might as well make it your own and modify it so you can sail it single handed when ever you want. then when you do have company you can have them lighten the load so to speak and let them feel like their helping while you smile and enjoy the company.
Run the lines to the cockpit install a down haul or splurge for a furler its an easy winter project that you can spread over a few winters making your boat "Yours". Either way get out and enjoy it even if its just a coffee in the cockpit on a afternoon off.
 

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She is spot on regarding get your lines situated:
so you can comfortably and safely control the boat all from the cockpit area.
run the mainsheet, the boom vang, and the topping lift all centrally, on the boom if posible,
Then you can hold/control the tiller & mainsheet in your back hand
You have your for'd hand to work the jib sheets, and also the vang out haul, or topping lift to depower when a gust hits,
and also at the ready to power up in an instant,all from right where you are helming solo.

As the sailor gurl said, when you are comfortable controlling your baby solo, you can invite folks an let 'em feel like they are helpin but you are confidently in control ! a song I remember once said, "the canvas can do miracles" this is SO true, & so much more true when you can do all the controls by yourself confidently and comfortably.

Spirit , my 26 ft. sloop & I came down from Lake Superior, Duluth Mn , we DO NOT miss the ice, now we are on the Mississippi at Grafton Il. down bound for Mobile Alabama. and the gulf 2018.
 

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Hi,
Some tillerpilots are relatively cheap and handy. I used to use a simrad tp-100 on a Dufour 1800 and it is great!
Cheers
 

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Had a small CD. Outboard was a sometimes thing.
Time to go sailing Yaaaa
Hank on jib, secure halyard and run sheets.
Pull main up on the mooring. Leave that sheet loose.
Go back to cockpit and start engine.
Go forward and drop mooring pendant.
Go back to cockpit and power off. If engine fails tighten main sheet and sail off.
Once got some room around me set boat on a near reach and secure helm.
Go forward and raise jib.
Go back to cockpit and tighten jib sheet.
Going home same in reverse.
Just make sure you have good stopper knots on all running rigging and you’ll be fine. Would note didn’t modify boat. Reefs/halyards at the mast. In someways easier. Nothing to jam. Think for anything 36’ and under still may be the way to go.
 

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N - that was a lovely read. Thank you so much. When I was working and had two or three days of no call or other responsibilities I would sail east for a day the west to get home. First wife thought I was nuts. Sometimes saying I was going golfing was easier than saying I was sailing by myself. Even now my favorite times on a boat is being the only one on deck. So Love night sailing. That pamphlet brings it all back. Now you got me thinking about doing my next passage alone.
 

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If you have ropes run to cockpit, you can also add a clutch to the mast.
I did this for the main halyard and it's golden when reefing.
You can premark mark them both places, cockpit and at-mast.
 

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Without autopilot you put the main up first (even in your berth or mooring) and then the boat always will come up into the wind if you don't have a hand on the tiller. Then u can raise the jib. Then you get gojng by back winding the main by pushing the boom to windward till the bow falls off.
This is awesome. I'm looking to single-hand a smaller boat sometime maybe this week and this is exactly what I needed to know, thanks!
 

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I would def rig a jib downhaul and run it to the cockpit. Doesn't take a lot of hardwear (mostly one block at the foot). turn into the wind and get the jib down. Also, even if no autotiller, rig a poorman's tiller tamer with some spare line and a bungee.
 
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