Here is the full list of all 31 Windward achievements. It takes around 40-50 hours to unlock all of the achievements on Windows.
Sink a pirate captain in a level 39+ region.
Repair your ship while obscured by fog.
Find and equip your first epic item.
Sink another player in PvP.
Defeat an enemy by yourself without taking any damage.
Defeat 100 ships.
Drop Grogolov on top of 3 or more enemies.
Defeat two enemies back to back.
Successfully complete a commission to place a Guard Tower near a town.
Completely drive out pirates from a level 9+ region.
Capture a level 9 or higher region in a co-op match.
Complete 50 commissions.
Defeat a Pirate Captain.
Upgrade your ship.
Establish a foothold in a region where your faction has no towns.
Achieve a skull kill rating.
Defeat 5 pirates.
Make a town grow in size.
Open a Sealed Letter.
Customize your ship's look.
Do your first trade run.
Complete your first commission.
Complete two consignments at the same time.
Hire a follower.
Unlock all ships.
Equip an item that will push any stat above 1000.
Become a true pirate. Arrr!
Opt out of a PvP match by using a White Flag.
Drive out pirates from a level 39+ region.
Achieve the Admiral reputation standing with any faction.
Complete the Strange Diagram quest.