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