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