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