Here is the full list of all 16 Jolly Rover achievements. It takes around 4-5 hours to unlock all of the achievements on Windows.
Sent a shipmate on a trip to remember
Escape in a hot air balloon
Defeated DeSilver
3x coconut knock-out
Rode a sea turtle
Found Silvereye's treasure
Sailed to Shipwreck Island
Infiltrated pirate stockade
Escaped Howell's Ship
Joined a pirate crew
Invented the trampoline
Found all pieces of eight
Found all crackers
Found all pirate flags
Earned maximum score
Completed game without hints