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I bought the SanJuan 33S that I referred to a while back ( here - SanJuan 33S knowledge ) well worth the money IMO.

thanks to those that chimed in on that thread, so far so good, I have had her out out in light wind, 2-4 knots and in 12-15 knots w/ gusts of 22-24 (per the anemometer)
So far she has had good manners and I am learning her nature as we go. The main sail is huge compared to my cruiser and the biggest issue I have with it is trying to flake on the boom 🤯 it has a rope luff and having the whole sail ‘free’ is a handful
The self tacking jib-is a mystery- I believe it was rigged incorrectly but I have never seen one nor can I find good pictures of the setup. I can only find one 33S for sale in the world but have yet to get pictures of the fore defect to compare.
I have tried to rig like a main sail traveler but that doesn’t work smoothly and quite honestly, seems labor intensive, which would be counter productive to having a self-tacker to begin with.
It has a radius curved track, a center car with 2 blocks, a block that connects to the clew of the sail. There are pad eyes at either end that also have blocks attached. A single line runs from the cockpit to the port pad eye block then to the port car/block then to the block at the clew, then the starboard car/block then to the starboard pad eye block and back to the cockpit. Does this sound right?
My mind tells me that you should be able to trim the car on the track same as a traveler and there are small pulleys under cat but no lines, when I attempted to add controls it really complicated things…🤔. If any one has any experience with these beasts I would sure listen to some input. I’ll try to get some pictures if that would clear it up any
Thanks
Cloud Sky Boat Naval architecture Boats and boating--Equipment and supplies
 

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In the Eastern Caribbean, it was a rare day when we, and most of the other cruisers, didn't have at least one reef in our mains. It is certainly much easier to shake out a reef when sailing than to tuck one. Consider sailing reefed until you can furl your reefed main easily.
 

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I'm looking at your neighbor boat with the black sailcover on the Main. The guide lines you see above the furled main, might be worth trying it, it will "stack" your main, so one less chore when lowering it.

If you mostly singlehand, keep the self-tacking jib arrangement. I don't like them, except when singlehanding it, then I love it.
 

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The rope luff is more suited to rolling the main. If you want to flake the main on the boom you might want to consider getting a sailmaker to convert it to sliders so that the luff of the sail remains captive on the boom, particularly if you are flaking it by yourself.

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Adding either lazy jacks or a stack pack will make handling a luff bolt rope mainsail much more difficult. Either of those simply make raising and lowering a bolt rope sail way harder.

As others have rightly suggested, the most effective and least costly option would be to have a sailmaker add slugs (slides) to your mainsail. This will greatly simplify raising, reefing, dousing, and flaking the mainsail. The slugs will keep mainsail on the boat and attached to the mast.

That is exactly what I have done with my mainsail. Within weeks of buying my boat, I had slugs added to the mainsail. A few weeks later I removed the lazy jacks because they made single-handing wildly more difficult. My boat has a similar rig to the San Juan 33s, except my mainsail is roughly 50% larger and weighs in a little over 100 lbs.

Based on my experience, once you add slugs, flaking the mainsail solo gets quite quick and easy even for an old guy like me. The trick is to start by 1) checking that each of the flakes between the slugs falls to opposite sides of the sail at the luff, 2) that you have sail ties in you pocket or hung on your neck, 3) that the mainsheet is tight and traveler is hard over to the side that is opposite from the side where the sail is on the deck, and 4) that all of the sail is on the deck on one side of boom.

Then, standing on the opposite side of the boom from the sail on the deck, starting from the clew of the sail make folds that results in parallel folds that line up with the folds at the mast. Once you are roughly a quarter of the way up the sail, tie on a sail tie and keep moving up the sail adding sail ties as you go.

Once you get used to it, your life will be much easier.

Jeff
 

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Or install the slides and a Dutchman system.
I like the Dutchman System for really big mainsails on cruising boats where the sheer weight and size of the sail, makes sail handling a lot more difficult. Conversely, this is a pretty small and light sail. The cost to add the system, and modify the sail and the sail cover to allow the use of a the Dutchman System would be disproportionately expensive relative to any gain in ease of use. I respectfully suggest that with a sail of this weight and size, it becomes just a matter of practicing flaking the sail before flaking the sail becomes second nature and no big deal.

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I understand what you are saying Jeff. But as a fellow older sailor, I would have a much tougher time single handing my 33 footer without the Dutchman system. I guess I am spoiled.
 

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I understand what you are saying Jeff. But as a fellow older sailor, I would have a much tougher time single handing my 33 footer without the Dutchman system. I guess I am spoiled.
Jim,
I see nothing spoiled about that. Raising and flaking the mainsail, and spinnaker raises and drops are the hardest things that I do on my boat. I have been very fortunate to be able to do these things at my age and know that there will come a time when I cannot do these things on my own.

My wife is still annoyed with me over an incident that occurred while I was flaking the mainsail during a summer cruise. A really big powerboat wake hit the boat while I was flaking the mainsail. I typically hang onto the boom with one arm wrapped over the boom supporting my weight and keeping the flaked portion of the sail from unraveling. I had not properly cleated the mainsheet, so the boom rocked out over the rail on the side of the boom that I was standing on. I ended up riding the boom out over the rail and then back aboard again. It was no big deal to me...All in a day's work, But as my wife pointed out, "Someday your luck will run out, and you won't be that lucky." She is of course right. I am not in my 60's anymore, and so need to be careful and should not be taking those kinds of chances.

Which is all a long way of saying, I fault no one for taking any measures that makes sailing easier and more comfortable for them as a way to keep sailing as the sand pile gets larger at the bottom of the hour glass.

Jeff
 
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Once the mainsail luff is attached to the mast with slugs the lazy jacks or a stackpack is the next step to making the mainsail manageable. The stack pack is just a sail bag incorporated into the lazy jack system.. with that you just have to drop the sail, the lazy jacks guide the sail into the bag, and you just tidy the sail a bit and zip it up. When reefing the stack pack contains the loose Sail so there is no need to lash it to the boom.

A stack pack makes classic mainsail handling a breeze.

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As others pointed out, have slugs installed on the mainsail luff and keep the track lubricated with Sail lube or the equivalent. Older and light weight sails are easier than new or heavy cloth sails to handle. You probably don't have heavy weight sails on your boat. The self tending jib is a complication. Does it have a boom? Our staysail has a boom and mostly I like it. It all depends on how well it was rigged and how you use it. If you single hand in very close quarters then you will probably come to like it more than if you sail in more open waters. In a moderate sized sloop such as yours, I would probably not go for a self tending jib. But if it's set up well it may work great. We have long had the rule to not change a boat until we have used it a lot. Sometimes what at first seems like a better idea really isn't .
 

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Why do lazy jacks make single handing more difficult?
I don't think anybody said that. (Or did I miss something?)

Lazy jacks for the most part make sail handling easier short handed. I have heard the argument that when hoisting the sail the battens can get fouled on the lazy jacks, but I would suggest that is more of a technique problem than an inherent flaw in the lazy jack system.

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Why do lazy jacks make single handing more difficult?
I think I was the one who said that lazy jacks make short-handed sailing much harder and removed the lazy jacks from my boat after sailing with them for a short period of time.

But my issues were that lazy jacks keep the sail close to the boom, but that comes at the price of a number of inconveniences. During raises battens tend to catch in the lazy jacks. Similarly they cause the sail to bunch up at the gooseneck making it harder to use two line reefing.

Proper sail care requires flaking or rolling the sail. That is much more difficult with lazy jacks in way, and gets almost impossible single-handed.

With the type of mainsail with a bolt rope instead of slugs that the original poster has on his boat, there needs to be a prefeeder a couple feet below the entry port and lazy jacks prevent the prefeeder from working.

Jeff
 

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I don't think anybody said that. (Or did I miss something?)

Lazy jacks for the most part make sail handling easier short handed. I have heard the argument that when hoisting the sail the battens can get fouled on the lazy jacks, but I would suggest that is more of a technique problem than an inherent flaw in the lazy jack system.

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Jeff said so above. Or maybe that’s not want he meant? I agree that they make things easier. Mine will snag a batten unless I keep the boat pointed the right direction but like you say, that’s technique.
 
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