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