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