Once outside of the boarding school, you should head directly for the drugstore. Unfortunately, Jeff is low on money and he can't use the ATM so go ahead and sell all of your cookies and the Broken Spray Can. Buy what you can and use the phone to save your game. When asked to buy some gum for $1, do so and offer some to the monkey standing by the door. It'll join you!
Jeff is at a fairly low level, so you know what that means don't you? Right! It's time to train!! Head south until you come upon an isolated tent. Inside you will be able to rest up for free, so fight around this area and rest when you get low on energy. Avoid Gruff Goats at all costs. While they give a lot of experience, they are extremely difficult to defeat and will more often than not kill Jeff. Instead, fight the easier enemies until you are at a high enough level to take on the Goats. It is recommended that Jeff be level 6 before heading on to the next area.
Head even farther south and you'll come upon a bunch tents. Talk to the people inside and you'll hear about the Tessie. There is a phone in one of the tents where you can save your game. Another tent will let you rest up. Be sure to also have some of the club chef's stew. When you wake up, go outside to the little dirt patch on the land jutting out to the sea and give the Bubble Monkey some gum. Tessie will take you to a new part of Winters!
 Brick Road's Maze
You will come to an area with a cave entrance and a pencil statue (too bad you don't have that Pencil Eraser!). Enter the cave because it is the only place to go and you'll be in a maze. There are a few presents in here so make sure to try and find them all. If you make it through the maze without grabbing all the presents, you can come back in and get them without the worry of enemies being in the way. Read the sign in the middle of the maze to have a photo taken by the "Fuzzy Pickles" man.
Save and exit the maze. Brick Road will restore your HP when you leave. You'll soon come upon another cave. Enter here and fight attack slugs to gain some more experience. Climb the first set of ropes for a Cheap Bracelet. Equip it and head back down and to the left. Here you'll find a Bottle Rocket. Take it and give some gum to the monkey for access to the next rope. When you reach the top you'll see a Sanctuary Boss! If you try and fight it, you'll be denied, it is looking for Ness instead. Head to the left out of the cave.
You are now at Stonehenge, where there are Caveboys running about. Be very careful of these enemies, as they can hit you for a lot of damage (about 40HP every hit). If you decide to fight one, bash it with all you've got and use food when your HP drops lower than 40. The Caveboy misses often so you have a chance. They give a lot of experience and usually a Picnic Lunch so it is well worth it to fight. Also, don't forget to get your picture taken by standing just south-east of the hole in the center of Stonehenge. When you're done, head south.
Enter the large laboratory and talk to the man inside. It turns out he is your father, Dr. Andonuts! He instructs you to use the "Sky Runner" to get to Threed, but before you are leaving, go upstairs and open the present, there's a Broken Pipe inside. Go downstairs now and head over to "Sky Runner". Press the button on the controller to lift off, and fly to Threed.