Hi all,
I first put this in another area till I realized that it did not really address the question that started the area, so I re-post it here. Sorry for any confusion.
I wrote this first back in 2016 and have recently edited it further for a friend. Please come back with questions/comments/thoughts.
I would hope this would be helpful to anyone thinking about new sails, though much is directed to cutters.
Dick Stevenson, s/v Alchemy

Sail Plan, Alchemy, 2016                            (edited 12-19)
Notes: the following plan is for a Valiant 42, a true cutter –(meaning mast almost amidships)- but may also apply to a double headsail sloop, often known nowadays as a cutter-rigged sailboat. The following plan is “optimized” (my judgment) for offshore sailing where sailing well is balanced with the ability to easily handle sails shorthanded over a wide range of wind speeds and seas conditions. All sails (except asym) are of various weights of HydraNet Radial. All construction is radial. (Choosing headsails—and their construction--for a sloop, even double headsail sloops, calls for different considerations). I am also happy sailing at 80% or so of the boat’s potential, especially off-shore. It is in squeezing out that last 20% that damage to boat and/or injury is most likely to occur.
We are very happy with the following:
A high clewed jib topsail of about 110%.
A robustly built staysail (on a roller furler), low clewed and of working size.
A main with 5 battens, good roach and 3 reefs, the third reef deep and approaching a trysail size.
An asymmetrical spinnaker- what I call our “offshore asymmetric spinnaker”- about 1200 sf (about 2/3rds the size and heavier built than many might recommend) made of 1.5 oz nylon, flat cut and serviceable from ~~60 deg off the wind to DDW (see article on this sail for details).
This sail combo has covered our bases for many years and approaching 70,000 miles and there is nothing I would do differently right now.
There are 2 other essays which will augment this one, the first describes the “offshore asym” while the other describes our use of a whisker pole, written in hopes that our methods will diminish the trepidation that many skippers have toward using a pole, especially husband/wife teams. (If reading this in the OCC Forum, both essays are posted in the Forum.)
Headsail choice
Random general thinking:
With regards to headsail choice, the difference in jib clew height and sail size matters much less when close hauled than it does the farther off the wind you go. As well, a smaller jib matters less if the skipper is comfortable getting out the asym when wind gets light and AW is at or behind a close reach. Then there is the skipper’s proclivity to use his jib/genoa reefed. A deck sweeping jib/genoa reefs far less successfully in a number of ways to a higher clewed sail. A skipper that needs the jib/genoa reefed often (and/or deeply reefed) will be much happier with the more symmetrically shaped sail (higher clewed). There will be much less need for jib lead/car adjustment and the sail will be shaped better for upwind sailing not having all that sail rolled up and bunched together down low. Finally, I believe there is little loss of speed using a high-clewed jib, say a 110, where the leading edge remains the same and only the amount of sail area changes: far less important for up-wind sailing. This is particularly so when paired with a 100% low-clewed staysail which catches the deck level wind when the wind is forward abeam. (True cutters have enough space -J length- forward of the mast to allow both sails to “breath” properly and produce drive.)
I would not call this high-clewed sail a yankee, but rather a jib topsail: I think of a yankee as a smaller sail. (The meaning/definition of yankee, similar to that of a cutter, both with their romantic overtones, has led to abuse among those who want to romanticise their products to facilitate sales and has led to the definitions becoming fuzzy in use: hence my use of the awkward phrase ”true cutter”). Abaft abeam (or even up to a close reach), use of an asym can make up for the headsail size in light air. (Actually, I use my asym for apparent wind of 60-70 deg to DDW- see description in paper: “Alchemy’s Offshore Asym”). That said, it is also clear that down-wind the above sails alone (without the asym) can move the boat nicely when using the pole in any winds over ~12 kn true.
Close hauled sailing, there is a range, say roughly 12-20 knots true, where the boat starts to feel uncomfortable and over-powered (this depends to some extent on temperature: we have been very surprised by how much more powerful a 15kn breeze at 40F/5C degree is compared to 70F/20C). One is tempted to just sail comfortably, if a bit more slowly, with the staysail alone, which, in calm seas, is a delight, but with chop, swell or more, there just is not enough “punch” to shoulder through the seas. This is where I sometimes reef the jib. If not far to go, I often opt for just going more slowly and comfortably and roll the jib up completely as reefing headsails works, but always leaves me a little unhappy. Above that wind range, the jib is usually fully put to bed and the staysail alone is used. This allows the jib topsail to be constructed and optimised for this limited wind range: a single head-sail rig must have the jib constructed to tolerate a much higher wind range. (Another way of saying this is that my jib topsail, even reefed, never sees apparent winds above ~20-22 kn while single headsail boats jibs must be able to handle much higher wind speeds).
Sailing with just the staysail remains powerful as the staysail shape is uncompromised for upwind sailing (contrasted with the shape compromise of a reefed jib, especially if low clewed). A headsail which is often reefed is also likely to have its life shortened as roller reefing is always hard on a sail. These considerations are often overlooked by sailmakers who do not have much experience with cutters (or double headsail rigs) or who do not inquire in depth as to how you sail your boat.
Also if you use a whisker pole a lot, (and we do now as this sail combo with our lightweight fixed length carbon fibre pole makes wing-and-wing sailing safe, easy and fast) higher clewed jibs keep the pole higher -less chance of rolling the pole tip in the water- and set the jib more symmetrically fully facing the wind (easier to get downhaul tension on a higher pole) and visibility is excellent. (See further Alchemy’s whisker pole paper on the use of the pole and a recommendation for a fixed length carbon fibre pole)
In summary: The advantages of a jib topsail, a high clewed 110% sail used in conjunction with a lower clewed staysail, are many. With regard to sail shape, there is superior sail shape off the wind. On the wind it has a long leading edge for reasonable power in anything but the lightest winds. When roller reefing, you are roller reefing a much more symmetrical shape, so you do not get the bulk of the sail area around the lower 1/3rd of the sail as you do when you roller reef a deck sweeping/lower clewed genoa. The foam (usually foam, mine is un-squashable rope) insert to augment sail shape when roller reefed is a sailmaking art form and not easy to execute properly, but is far more difficult with a deck sweeping genoa. The greater percentage of sail area up higher maintains contact with better wind when negotiating the ups and downs of ocean swells and the vagaries of wind direction. Finally, being able to have the pole up high, less likely to roll into the water, when going wing and wing down wind is, to me, a big safety factor.
Advantages (not in order of importance):
1.    The headsails work synergistically: the low-cut staysail catches the wind low down while the jib topsail works with the higher more powerful breezes.
2.    The sail area combined is almost as great or greater than a genoa.
3.    Higher clewed jib topsails are faster with less heeling when on reaching points of sail due, in part to far less twist-off and the lead being further aft.
4.    The 2 sails give one far more opportunity for combinations to respond to changing wind speeds/directions without need to resort to roller-reefing. Or in other words, one does far less roller-reefing with its stresses on the sail and its poor shape while covering a far wider range of wind strengths and AW directions. Smaller sails on 2 roller furling systems (my roller furlers are also each oversized) make for easier sail handling and furling.
5.    The high clewed jib topsail is balanced better on a roller furler and, more importantly, if reefing is necessary, it reefs far more satisfactorily as it decreases size symmetrically and needs far less jib lead adjustment (maybe none). The lower clewed a sail is, the worse it will roller-reef as so much sail area is bunched up low leaving sail shape compromised. No amount or distribution of foam on the leading edge will make much difference. Roller reefing is very hard on sails and hard on equipment (like the pennants). All this is less potent a consideration for the staysail as it is so much smaller and reefed far less often.
6.    In the open ocean one wants punch to power through swells and waves. A higher clewed jib topsail (with a staysail) sustains this punch into seas much better than a low clewed sail. This is, in part, because the jib topsail stays in better air when at the bottom of swells and the whole boat (and crew) benefit from sustained predictable pressure on the sails.
7.    A low clewed genoa interferes with vision forward (one needs to frequently position oneself in awkward positions to see forward under the sail when on watch-this can get old really fast) and is prone to catching waves in its skirt with all the problems this can entail.
8.    If you seldom use your whisker pole, be ready to shake the cobwebs off. A high clewed jib topsail is a delight off the wind. The pole stays quite high and is little danger of being rolled into the water. Vision is unobstructed. The range of apparent wind angles able to be sailed increases dramatically over a low clewed genoa. The jib topsail, being a far more “symmetric” sail, it reefs far more satisfactorily. And (I believe) there is little to no loss of power as the wind is steadier and better up high.
9.    Close hauled there is little difference in all but the lightest of airs as it is the leading edge, roughly the same on both sails, that generates the power and lift. On a reach, the lead being far aft, sail shape is often much better as genoas tend to twist off unless very well sailed and attended. And, unlike a double headsail sloop with its shorter J and more constricted air flow, the staysail contributes to upwind performance.
10.    On our size boats, storage is, for me at least, an issue. The only sail we store below is our asym which goes on a forepeak shelf. I work hard not to have our aft cabin become a “garage”.
11.    The above all works in combo with my asym which I have written about before. A good asym can cover a lot of a genoa’s bases. I can carry mine to 70 degrees AWA (60 AWA with flat seas), which makes some of the rational for a genoa go away.
12.    With the above sails, I believe I can (almost) always sail at 80% of the boat’s capacity. More than that I am not usually interested in as I believe damage to boat and persons become far more likely when you attempt to push into that last 20%. The boat also tends to get less comfortable and I am cruising, not racing.
13.    A thought: in open ocean sailing the ability to punch through swell and maintain speed in chop transcends pointing ability. I am willing to give up a few degrees of pointing ability to have the power to shoulder aside swell and waves.
14.    All my sails are radially cut. They hold their shape far longer and when the headsails are roller reefed, the shape is far better than would be the case with crosscut sails, especially in the long run. I also do not believe the price difference is all that great in the long run and I do not have to suffer through compromised sail shape to get an extra year or two life-span. Valiants sail well and I like to sail well, so spending a little extra up front just works for me.
15.     I also wanted quality low stretch cloth. We used HydraNet Radial cloth and it is a cloth, cloth being important in the wet higher latitude sailing we have been doing means the sail “breaths” and dries out and is far less prone than laminates to mold intrusion and, of course, to delamination. The cloth is quite slippery, so repairs are necessarily sewn rather than using the sticky backed Dacron that worked well in the past. “Sail Dr.” epoxy sail repair glue has worked well in experimentation.
16.    We have 7 seasons (of 6-7 months) of mostly higher and high latitude sailing and one Atlantic crossing and, knock on wood, have experienced no repairs. Sail shape is still excellent where I know from past experience that Dacron sails would have a sail shape that had been disappointing for a year or more by now and I would be planning for new sails. I am not convinced, in the long run, that my high quality are that much more expensive as they hold their shape so much better and longer. Besides, Valiants sail so well, that you have the pleasure of sailing her at her best over the years.
There have been very few times I have wanted my headsails different than described above.
Mainsail: (again not in order of importance)
As said above, “A main with 5 battens, good roach and 3 reefs, the third reef almost of trysail size”.
1.    My main is fully battened with 5 battens. A bulletproof design for the batten pockets is imperative.
2.    I think slippery sail car slides are terribly important for an off-shore boat (Antal and Harken and I have heard good things about Tides), both for ease of use and for safety. The ability to reef and douse going downwind can’t be overstated as a good ability to have. Without slippery track, perhaps only the top 2 battens should be full. This still allows for a fuller roach and better pointing ability.
3.    We certainly considered a trysail long and hard, but decided that the rare times we would need it we would go with our deep third reef. The argument that a trysail can save a main being destroyed in a storm is valid. Our thinking was that the likelihood was slim and when/if it occurs, we will limp into port with a patched main and just have to buy a new one. Our sails are always in good condition as I like to get new sails based on shape and set rather than cloth strength. (Setting up a trysail to be a useful addition to the safety of a vessel can be, and usually is, a logistical challenge. It has been no small task to the very few I have talked with who successfully accomplished and had recourse to use their tri successfully.) With this choice of no try we might heave-to more readily without a try or choose to go downwind with a drogue a bit sooner.
4.    In practice, we use our 3rd reef once or twice a season and in 2 ocean crossings and multiple off shore passages have never wished for a try. A not insignificant advantage is we do not have another sail for which to find room to store it.
5.    I hate the luff “chatter” that can occur sailing upwind. Last mainsail I had the mast cars attached to the sail with a medium sized shock/bungie cord rather than sewn/lashed. They have lasted well (7 seasons) and I have had no chatter. I also think they are likely more forgiving in a gust etc. thereby protecting the sail a bit.
My best, Dick Stevenson, s/v Alchemy