All games are ultimately in the business of a selling a fantasy. The best ones conjure up a combination of presentation and mechanics that lets you imagine, for a few fleeting hours, what it would be like to live a different life: a criminal, a superhero, a racing driver, a soldier. OK, most of the time it's a soldier.
There's no shortage of games that let you march in the boots of ground troops. Sailor, on the other hand, tends not to rank too high on that list, though there have been notable attempts to recreate a life on the ocean wave in gaming. Assassin's Creed: Black Flag was the closest that mainstream blockbusters have come, but for most vintage players it's Sid Meier's Pirates! that remains the standard bearer for nautical action.
That's also the game that is most clearly the inspiration behind Windward, a maritime RPG that promises the chance to explore, trade, barter and battle your way through a procedurally generated world. It's a promise that the game sadly can't quite keep.