CLOSE TO THE WIND • E-FREE TRANSLATION.COM • Definition of Close to the wind

... quotations and invariably did so. He seldom made a mistake and never admitted the mistakes he made. His transactions were honest because his knowledge of the law was unrivalled and he knew to a hair how close to the wind a man might sail. As he never wasted a moment he occupied the time of waiting, in ringing up his broker and firing a barrage of instructions. This done he returned to the fireplace, consulted his own ...

— Men of Affairs • Roland Pertwee

... the sense to "steer a straight course," but, getting "half seas over," perhaps "go by the board" or be "thrown overboard" by friends who might have "brought you up with a round turn" before it was too late. Remember three other bits of handy man's advice: "you'd better not sail so close to the wind" (do not go so near to doing something wrong), "don't speak to the man at the wheel" (because the ship may get off her course while you are bothering him), and, when a storm is brewing, mind you "shorten sail" and "take in a reef," instead of ...

— Flag and Fleet - How the British Navy Won the Freedom of the Seas • William Wood