Drilling Sailcloth

Dont think I'd want to do that with even half-decent twists bits, especially when AFAICT a nail would probably do it a bit better with less manipulation.

But I could be wrong

FWIW, I use bits of nail in an old soldering iron to pierce synthetic fabrics.
 
Good advice above.

One of my favorite methods for materials that do not melt well and larger holes (if I don't just want to use a standard punch) is to sharpen a short length of steel tubing and chuck it in a drill. A few days ago I need to drill ~ eight 1/4-inch holes in 5/16-inch reinforced rubber, and this knocked out perfect round holes for the bolts in seconds (drill press). Do remember to clear the tube every other hole. So fast and clean. Also good for leather. Resharpen often, as it is not tool steel (just run the drill on sandpaper at the correct angle for a few seconds).

A tube is better than a drill, which usually makes rather of a mess of it.

But I would more likely melt small holes in sailcloth. It depends on the size, material, and purpose.
 
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