Windward is set in a world that grows with you. The game is easy to learn, and there's nothing overly complex, so players will quickly get into it without much of a learning curve. Even better is that as your ship improves and your talents grow, so do the pirates and the allies you encounter. This can lead to entertaining in-game encounters, such as allies exclaiming, "Hey lads, there's (your ship's name)," when they sail near your vessel. But the overall essence of the game is a simple sailing sandbox game without an overarching story line or "save the village"-type goals. In effect, Windward is very much like a light version of Sid Meier's Pirates, in that it lets players determine what they want to do when they want to do it.
That means players can choose to sail the seas, charting the islands they come across, perform trade between different ports, or go hunting for pirates. The way you play will help direct the upgrades you'll want to make to your ship, as well as the kinds of skills your captain acquires. What's nice about the open nature of the game is that if you make a bad decision, you can quickly and randomly generate a new game world or edit it to your liking. That's actually necessary, because while the open-world nature of the game is one of Windward's strengths, it actually winds up being it's greatest weakness. Since there's no story, players will find themselves constantly sailing from one place to another, which quickly becomes repetitive and boring. Sailing and boat fans may find Windward amusing for a while, but unless you're willing to make up stories on your own about your captain and crew, you may play it for a while and then look for a more directed story experience.