In modern English, gales are not pleasant things. They make us sea-sick, cause nautical disasters, and damage houses.
If gales are forecast, we avoid them. This strong sense has been around since the 16th century, but it developed in parallel with a milder sense, where the word meant simply "wind", without any connotation of severity or danger.
Often, it was synonymous with "breeze", and conveyed the pleasant connotations which that word has today. In Shakespeare, usage is entirely in that direction, with the word being accompanied by adjectives with strongly positive connotations. Gales can be "merry" (in King Edward III, III.i.77), "happy" (The Taming of the Shrew, I.ii.47), and "auspicious" (The Tempest, V.i.315). In Henry VI Part 3, King Edward has been worrying about the "black cloud" of the enemy. "A little gale will soon disperse that cloud", his brother George saysto him. The concept of a "little gale" seems paradoxical, until we remember the milder meaning of the word in those days.