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