I don't really play sandbox games, as I get bored easily by arbitrary goals that usually mean nothing to the game, but something about Windward raises my sails (pun completely intended.)
Windward relies on few basic mechanics that sometimes fall short. Nonetheless, It has the potential of giving hours of mindless enjoyment.
Windward is a fun RPG for customization, but unfortunately it becomes tedious and repetitive very quickly. However, it is more fun to play multiplayer and hopefully we will get to see some expansion and DLC very soon.
A very nice entry into the naval sandbox genre. Perhaps the only entry worth considering, and a great game in its own right. You can explore a vast world and do whatever you please to achieve your goals.
If you're looking for something similar to Sid Meier's Pirates, you will find Windward to be frustrating and boring, running in circles around the map and around enemy ships, with random gear upgrades and dull content.
Tasharen Entertainment has struck a gold mine of nostalgia within me.
Fun in a simple, almost mindless way, the oceans of Windward are beautiful but not especially deep.
But Windward is neither of those things. After dozens of hours it still has you doing the same monotonous tasks you did at the very start, even as you claw your way to a slightly better ship in which to run your errands. For a game set on the deep blue sea, it's unforgivably shallow where it counts.
Windward is less of a high seas adventure and more of a soporific cruise for the geriatric crowd.