Bet with him. Give him the fish to get the fishing pole. Booty Isle Cliff Walk to the side of the cliff. Use the fishing pole on the map. A bird will take the map away.
Big Tree Walk to the big tree.
There is a plank in one of the hole. Pick up the plank. Use the oar in the first hole. Walk to the tree and then stand on oars. The oar will break and you'll have a dream.