Here is the full list of all 31 Windward achievements. It takes around 40-50 hours to unlock all of the achievements on Windows.
Drive out pirates from a level 39+ region.
Complete the Strange Diagram quest.
Achieve the Admiral reputation standing with any faction.
Unlock all ships.
Equip an item that will push any stat above 1000.
Drop Grogolov on top of 3 or more enemies.
Sink a pirate captain in a level 39+ region.
Sink another player in PvP.
Become a true pirate. Arrr!
Find and equip your first epic item.
Opt out of a PvP match by using a White Flag.
Capture a level 9 or higher region in a co-op match.
Repair your ship while obscured by fog.
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 100 ships.
Defeat two enemies back to back.
Successfully complete a commission to place a Guard Tower near a town.
Defeat an enemy by yourself without taking any damage.
Complete 50 commissions.
Achieve a skull kill rating.
Customize your ship's look.
Complete two consignments at the same time.
Make a town grow in size.
Upgrade your ship.
Defeat 5 pirates.
Hire a follower.
Open a Sealed Letter.
Do your first trade run.
Complete your first commission.