The province of New Brunswick has a fine heraldic flag, depicting a ship (a three-flagged, single-masted, oared galley called a lymphad, as traditional in Scottish heraldry) beneath a fantastically elongated golden lion passant (a symbol of the Canadian monarchy, and of German Brunswick) .
What’s wrong with this picture? You might point out that lymphads have never been used in the Maritime Provinces, and that monstrous gold lions are seldom seen in apocalyptic red and yellow skies over Moncton. And you would be right. But that’s not what bothers me about this flag. I rather like the psychedelic heraldic imagery. Heraldic artists are entitled to artistic license.
What bothers me is that the direction in which the wind is depicted blowing on the flag is always the opposite of the way the actual wind is blowing when the flag is flying. (And since heraldic flags are “printed through” so that the reverse is the mirror image of the obverse, it doesn’t matter if you happen to be looking at the back of the flag — the real and imaginary winds are always opposed.)
Why didn’t the heraldic designer of this flag (Alan B. Beddoe, O.B.E., (R.C.N.V.) Rtd.) fix this apparent problem by having the ship head the opposite way: away from instead of towards the hoist? (Hoist is the flag terminology for the edge of the flag attached to the flagpole.)

Well, in addition to now somewhat awkwardly presenting an apparent chance encounter of an aerial lion headed to the left with a ship headed to the right, this would violate the heraldic principle that the direction of honor is away from the sinister (to the observer’s right) and towards the dexter (to the observer’s left). Turning the ship around would suggest it was, like Sir Robin in Monty Python and the Holy Grail, bravely running away, not forward.

Heraldry aside, when a flag is flying from a flag pole it has an implied direction of motion that is into the wind — and opposite to the actual motion the flag would have it it were to become detached from the pole. This idea that the forward edge of the flag is its windward one becomes more apparent if you imagine the flag flying from a moving pole, so that it is the motion of the pole (held by a marcher, perhaps) rather than the wind that is causing the air to move past it. By this flag-logic (which gives the same result but for different reasons than heraldry-logic), to be understood as moving forward, the ship needs to be facing the hoist. (This flag-logic is also the reason that “backwards” US flags are worn on the right shoulders of some military uniforms and placed on the right side of vehicles.)

This need to show vehicles (and people, and animals) facing into the wind only comes into conflict with the way the wind itself needs to be depicted on the flag when the vehicle is understood to be pushed by the (imaginary) wind. Take away the sail, for example, and the problem goes away — the imaginary wind can be shown to be moving in an anti-heraldic direction, consistent with the real wind, and (hopefully?) not raising any heraldic hackles.

However, the question of which direction is perceived as forward on a flag is larger than the particular problems depicting sailing vessels presents. But that is a subject for another time.
I’m not a sailor, nor will I ever be, but I’ve seen the way some sail effectively into the wind by tacking. I suppose this sort of tub couldn’t be made to do that.
What I find to be unusual is that heraldic charges are normally isolated on a field or smack on a partition between fields, not pictorially integrated like this one. The flag with ship and water adopted by Bath, Maine, follows the rule more strictly.
That flag has two flags on it! That shows why such flags are BAD. If the flag was a proper flag, it woudn’t have boats and lion on it. Great flags are abstract.
The sails and flags are correctly depicted with a wind from right to left (facing the picture). A sailing vessel not under power (not accounting for oar action in the picture) will not sail fast enough to “outrun” the wind pushing it along, therefore, the flags and ensigns will point in the direction of the vessel’s travel. . . .