Ahoy There - Ahoy! More Than Twenty Times

To unlock the achievement, sail to the adrift ship on the sea map where you’ll encounter some scurvy paranoid pirates. When you first see them, select the “Ahoy!” dialogue option and select “Ahoy!” 20 times until the achievement unlocks. Remember that this achievement is missable because after you retrieve the flag from their ship, the pirates go inside and you can no longer talk to them.
Achievements
Return to Monkey Island
legendofmi.com/

[@WolfBrothersCinema]

Ahoy

[@bflmpsvz147]

Ahoy!

[@kypello3512]

Ahoy!