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In order to win this Trophy, you must finish first in a toy boat race.
This Trophy invovles a treasure hunt.  After you find each clue, the next clue becomes avaiable.  You cannot skip clues.  After opening the first chest, follow the numbers marked in red.  Ignore the chest marked with an X.  It is just there to throw you off.
The battle with Peggie is much different than the battle with Earthrotter.  Peggie marches back and forth.  As you move around, he counts down to one.  When he gets to one, he jumps into the water, and his shipmates across the cave fire at you.  To beat him, walk around until he counts down to two.  When he steps above you, step into him to punch him and knock him out.  He'll take the blast from the cannon instead.  Repeat this for two more rounds, and you'll have the Trophy.
This is the only side-scrolling location in the game.  To get to the Trophy, avoid the pirates (or fight them, it's your choice), and grab the Trophy.  Don't worry about letting the pirates run into you.  They won't attack you unless you bump into them.  The same can be said with just about every bad guy in the game.
A mermaid has been captured by the pirates.  Bring back her three pearls so she can escape.  The pearls are circled in red.  One is at the back of the pirate ship, one is in the cliff under the Move Shop, and one is in a corner of the sand castle.
There is a shortcut in this race course that leads to a ? Token.  Look carefully, and you'll see that one of the rocks is slightly off color.  You can go through this rock.  Just follow the arrows shown above.
In order to reach the ? Token and the mermaid's pearl in this cliff, you need to get the Spring Boots at the Move Shop in Mt. Snow.
In order to enter the sand castle, you have to beat Peggie in the cave below.  After that, you have to use Form Swap on one of the pirates (not the one guarding the entrance).  If you haven't learned Form Swap, go to the Move Shop.  After all this, then you can enter the sand castle.  Form Swap will wear off the moment you enter.
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