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