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