sail against the wind

sail against the wind

To work to achieve something amid challenging circumstances, such as staunch opposition. This nautical phrase refers to the difficulty of sailing in the opposite direction as the wind. I know that I am sailing against the wind to try get this unpopular law passed, but I am confident that it will ultimately make our town a safer place.
See also: sail, wind
Farlex Dictionary of Idioms.

sail against something

to operate a boat or ship, so as to move against the wind. It takes skill and training to sail against the wind. The huge cruise ship sailed against the wind all the way to St. Thomas.
See also: sail
McGraw-Hill Dictionary of American Idioms and Phrasal Verbs.
See also:
  • sail against
  • sail before the wind
  • steady as she goes
  • batten down the hatches
  • batten down the hatches, to
  • hatch
  • take (something) in tow
  • sail near the wind
  • near the wind
  • helm
References in periodicals archive
For their time, they were the perfect type of vessels; so light, they could swiftly sail against the wind. The Spaniards called them lanzaderas.
Rizal and Morga
Andrade is also correct that sailing in the Mediterranean, and up the coasts of Africa and in the Atlantic, required ships that could effectively sail against the wind. The Europeans here benefitted from the Arab designs (lateen sails) and developed riggings that combined the best characteristics of square and lateen rigging in various combinations to develop large ships that were reasonably fast downwind, broadside, and upwind.
An accelerating divergence?
Twenty minutes later, the captain continuing to sail against the wind, calm returned.
It can be said of Ted Kennedy: 'yes, he did'
Would you make a ship sail against the wind and currents by lighting a bonfire under her deck?
Howlers! (bet they wish they hadn't said that)