It is not too difficult if you don't rush things since if you try to complete the level quickly an Enemigo might knock it out of your hands and into the water. In that case, you'll have to restart the level. Just make sure that every time you jump on a new ship, drop the Anchor, then go on ahead and clear out all the Enemigos. After that, come back for the Anchor and carry on. Of course, you can also be a Daredevil and rush ahead if you want to, but that might result in failure. The most stressful bits of the level are when you're platforming across the water on boxes. One wrong jump can end your run.
There is one instance in the level where you'll have to get a bit creative. After the third ship, you'll have to ride a Zipline, however, you can't do so while carrying an Anchor. You'll have to use the Wooden Boxes under the Zipline to make a bridge by throwing them into the water. They'll float, and you will be able to get across.
- The description of the Challenge mentions a "Map Chest", which is what the Chest at the end of the levels were in the first game. However, in this game, the Chest doesn't contain maps. This can mean three things: either the developers copied-and-pasted the description from the first game and slightly altered it; or simply made a mishap while writing it; or decided on the Chest not containing maps anymore after this description has been written. The latter seems the most likely.