Sailing upwind

Jan 22, 2008
22
Catalina 275 15 Bellevue, WA
Hi Team,
I have a 2015 C275 (Hull 16). It has the small self tacking jib (Doyle) that came with the boat and a new Doyle main with a stack pack.

I love this boat for so many reasons...mostly that I can single hand it (with my auto tiller) and its easy to bring non-sailor friends out and let them take the helm while I do everything else. My favorite spot in the world is standing sideways on the second step of the companion way watching the lake and helping my friends steer the boat with gentle coaching.

The issue is that I can't get the boat to sail up wind closer than like 50 degrees off the apparent wind (I have a full complement of Raymarine gauges es that came on the boat when I bought it 3 years ago.

I have tried all kind of trim on the jib and I can't quite get it to sail any closer to the wind. Is this just the nature of this particular beast or am I doing something wrong?

BTW, while I appreciate all of the help here, I must disclose that the name of my boat is "Twenty Questions." Irronic?

Thanks in advance.
Mike
 
Jan 11, 2014
13,947
Sabre 362 113 Fair Haven, NY
How old and in what condition are the sails? Old stretched and baggy sails will not point as well as new sails.

The boom should be centered, this will place the traveller car above the centerline. The jib should be trimmed so that the upper and lower tell tales are breaking at the same time. The leeward telltales should be streaming aft. Achieving this trim will require adjusting the jib cars. This may not be possible with a self-tacking jib. The line described by the jib sheet should bisect the angle at clew. This will apply equal tension on the foot and the leech.
 
May 17, 2004
6,108
Beneteau Oceanis 37 Havre de Grace
I don’t know about the 275, but 50 degrees off the apparent wind shouldn’t be normal. 50 degrees off the true wind would sound more reasonable, so you may want to confirm you have the instruments set up to show what you expect. What happens when you try to go higher than that? Does the jib or main start luffing? Do the telltales go in wonky directions? Does the boat just get slow?
 
Jan 1, 2006
7,934
Slickcraft 26 Sailfish
There could be many causes. Davidsailor26 asks good question. Those answers will move the ball forward to maybe a remedy.
I start with an often neglected problem. Is the bottom clean and smooth? Dirty bottoms are slow and boats going slow don't create enough apparent wind to point.
You can also look at the tune. Forward mast rake won't want to point. About 3 degrees aft rake is more like it.
 
Nov 20, 2025
28
Alden 60' Schooner Killybegs
All good advice but I think the elephant here is the self-tacking jib. You should understand that your self-tacking jib almost certainly comes at the cost of limiting performance. There might not be much more to this mystery than that. Assuming your jib is limited to 100% or less, you just aren't going to get the best windward performance in lighter air where a larger genoa might be called for. In lighter winds you're just underpowered up front.

50 degrees is not ridiculously low. It is just too low for your boat which is probably capable of closer to 35 degrees with the right sails, conditions, and trim though you would want to back off of that to make decent VMG. But honestly, 50 degrees is close to what I would expect to see with a self-tacking jib unless conditions were ideal for it. You can't control your draft and the size of your headsail is limited.

You can probably squeeze out a little more windward performance but just recognize that your rigging probably imposes some limitations that no amount of fine-tuning will overcome.

I have a mate who loves his self-tacking rig but he also has a couple of snatch blocks on the rails that let him break out his deck sweeper in lighter conditions. He is still almost never as efficient as possible but it's good enough for him.
 
Jan 1, 2006
7,934
Slickcraft 26 Sailfish
The Alerion Express 28 has a "Self Tacking Jib" and is a pretty good upwind boat. Mostly those boats have the Hoyt jib boom - which is either an asset or liability depending on your point of view.
I'm not familiar enough with the Catalina 275 to comment on its "Self Tacking Jib."
 
May 17, 2004
6,108
Beneteau Oceanis 37 Havre de Grace
The Alerion Express 28 has a "Self Tacking Jib" and is a pretty good upwind boat. Mostly those boats have the Hoyt jib boom - which is either an asset or liability depending on your point of view.
Other model Alerions are rigged the same way, and I’ve lost enough races to them to agree they can point just fine. :banghead:

Plus they look nice doing it.
 
Jul 19, 2013
390
Pearson 31-2 Boston
This video has some detailed discussion of sail settings for cloehauled performance.
 
Jan 1, 2006
7,934
Slickcraft 26 Sailfish
Maybe it's just me but I get no sound on that video. But I'd be interested in what is being said.