First talk to Greg. The wind carries his last twenty dollars straight into the hands of two teenagers. They run away, and Greg chases them. Look for tokens which are scattered all around the Island. (Most of them can be found easily at the Boardwalk Rides and/or the Fun House.) Then, win all of the games except the Himalayan Hurl. When you're done, head left.
Next walk left until you find the Cranium Shaker. Go over it and click on the lid. Carry it to the trash can and click on it. Push the trash can over to the cotton candy stand and take off the lid by clicking on the trash can again. Now, click on it for the last time and dig around in the trash until you uncover the Bag of Popcorn. It is really similar to the mini-game where you uncover Linus's blanket in Great Pumpkin Island. Take it to the popcorn vender and get him to fill it with popcorn. Now head right until you get to the Boardwalk Beach.
Talk to the keychain photo seller and ask him to take you a picture. He'll give you Sunblock. Now get the Keychain Photo from the flying seagull and give it to the guy with the metal detector. He'll give you his Metal Detector. Now walk over to the sunbathing woman and drop your popcorn next to her. She'll run away because of the seagulls. Use your Metal Detector on her towel and the light on it will turn green.
Click on the light to get the Car Keys. Before you leave the beach, give the sunburned man the sunblock and he'll give you his Oily Suntan Lotion. Now go all the way to the left until you find the parking lot. There, give the woman her keys. She'll give you a pair of Flip Flops.
Now go over to the Boardwalk Arcade and put on the flip-flops. Go on the roof of the arcade and get the Flying Disc. Give it to Shawn (the crying kid). Then go to the claw machine and jiggle the lever. When you play, grab and drop toys until you find the Fake Vomit. Leave the arcade and go to the Bumper Cars ride by Boardwalk Rides. Drop your Fake Vomit near the line to get rid of it. Then talk to the manager and he'll let you in. To win the minigame, bump into Rowley's red car 3 times and he'll drop his Lucky Rabbit's Foot. Drive over it to obtain it. Now go back and play Himalayan Hurl. You'll most likely win it on your first try. You'll get the Jumbo Prize. Go over to the black kid with the Remote Controlled Helicopter and trade the Jumbo Prize for it. Now go to the Fun House and a preschooler will tell you that Rowley is stuck in the slide. Use your Oily Suntan Lotion to free him. He'll land in the ball pit and uncover Fregley. Fregley's mom will give you his leftover Fish Sticks. Now go back to the beach and put the fish sticks on your RC helicopter's hook. Lower the fish sticks to the crab and it will grab them. Now go to the money sticking out of the boardwalk. Use the helicopter again and the crab will pinch the money, making it stuck. After you go back under the boardwalk with Greg, the teens will run away and the money will flutter down into Greg's hand. Greg will give you the Island Medallion. Congrats!