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.
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.