Higemaru Makaijima/Ookami Island

Pirate Ship
You will find the Pirate ship with the key to the Ookami Island gate right off the north coast of Dokuro Island, right near your most recent location. The layout of this ship will be the same as the one you faced previously, requiring you to defeat 30 pirates before you can face the captain. Once you obtain the key from the captain, sail due east below Curse and Hebi Islands, and then into the alcove of Ookami Island. Reverse a little bit and travel back up to find the entrance on the left side of the north portion of the island.

Ookami Island
Ookami is quite easily the largest island in the entire game. It is composed of three different elements; a harbor, a fortress, and desert. For your first visit to the island, you won't really have to concern yourself with the fortress, as you will not be able to fully explore it until you've found the door to Baido's treasure at least one time. You really only need to concern yourself with the southern and western portions of the island.

You will arrive in the upper left corner of the map. When you enter the gates, you will meet some of the Higemaru pirates, but these pirates don't mess around; they have the ability to pick up and throw barrels at you, just as you do. And they will use that ability to get the best of you. It's important to try and take them out as quickly as you can. If you do, you will notice that the enemies are finally starting to give you a substantial amount of health points back for defeating them. On Ookami Island, the first is worth 50 points, then 100 points, and 200 and 400 and so on. On the screens that resemble harbors, it's difficult but possible to earn 750 points if you manage to defeat four pirates with one barrel. You will also find Scorpions on the island, but they are less of a threat.

Start by travelling right from the entrance, and go south at the fork in the road. Follow the path way around and down the west coast of the inside of the island. You will pass a screen shown to the right with a broken bridge. The method to complete it is not known to you at this time, so keep going south. When you reach another fork, head left, and pass through another harbor until you reach the desert where you'll see a large cactus. Head south one screen, west one screen, and north once to reach the boss of the island.

Boss fight
The boss of Ookami Island is a monkey known only as Fire Kong. For whatever reason, this large ape can breath fire at you when it pounds on its chest. For all intent purposes, this boss is no more difficult than any of the others you have faced. It will remain near the top of the screen, and will send blasts of fire at you at various intervals. Simply pick up rocks and throw them at him until he is defeated. When he is, you will gain access to the screen up above. Walk there to find a map on the ground. If you collect it, you will gain access to the map on the subscreen. At this point in the game, the map won't do you a tremendous amount of good, but it is handy to reference every now and then if you get lost at sea. A little anchor will show you your current location. Unfortunately, you have to dock your ship at an island in order to use it, as it can't be viewed while sailing.