Freshly-Picked Tingle's Rosy Rupeeland/Hometown Prairie
You, a 35-year old, single man just minding your own business (or lack thereof), are one day summoned to the pool just west of your house by a mysterious voice. Leave the house and head west. Going east or north will cause the voice to stop you, stating he clearly said "west". Once at the pool, touch the surface of the water to find out the mysterious voice belongs to an elderly man with a Rupee-shaped head. He introduces himself as Uncle Rupee and asks whether you'd like to go to Rupeeland. Uncle Rupee then describes Rupeeland as a Cockaigne-like paradise. Answer "Yes" when he is finished. He'll then transform you into Tingle, which subsequently will be your new name.
From this point on, rupees are everything. Rupees are your health. Run out of them and you die. The game doesn't allow you to willingly kill yourself, so when you attempt to pay for something, you can not spend everything you have. You'll always keep one rupee. The only way to run out of rupees is by losing them in battle or because of a trap. Rupees also are your way to progress through the game. You can't reach a new island if the Tower doesn't become taller, which it only does if it is fed rupees. The Tower can even shrink if it isn't fed for a long while. Luckily, it doesn't require a lot of money to keep it at its current height and you'll receive a warning shortly before it is about to shrink. If that happens, immediately return home and feed about 100 rupees or more to the Tower.
Before leaving on your quest to gain as much rupees as possible, you are first given 100 rupees to start. However, you are also required to donate a bit of it in order to leave. 1 rupee will do, and since you can use all the rupees you can get your hands on right now, this is recommended. When you've left the pool, you'll be contacted on what seems to be a Tingle Tuner by Pinkle. She introduces herself as your assistant for the rest of your quest. She'll ask you to go to your home and save the game. Return home and notice the glittering box just right of you. Open it to receive a Bottle and 50 rupees. Then head to the terminal in the upper right corner and save the game. A new option will become available: "Talk". Select it to hear an explanation of the basics of the game or have a nice chat with Pinkle. Close the terminal and you will get the Tingle Fireworks recipe. There currently isn't much of interest in your house. The Cooking Pot in the lower left corner is used for cooking, but since you currently have only one recipe and no ingredients, it can be ignored for now. The machine in the upper left corner is where you stash anything created by cooking. You'll need Empty Jars to actually take the stuff you created with you. The attic is where the Rupee Goods will be stashed.
Leave your house and head east, then north. You'll encounter a young girl named Aba who offers (for free) to train you in the arts of battle. Accept her offer to learn the game's battle mechanics. After that, go north and a little west to meet the Town Map-Seller. She's an old lady that tries to make maps, but because of her lack of drawing skills, can't. Talk with her and you'll be given the Hometown Prairie map and asked to draw the grave between the two trees. Drawing a landmark on a map is done by drawing a properly sized circle where the landmark is located. If successful, a drawing of the landmark will appear. The Town Map-Seller will compliment you on your drawing skills and ask you to help her making maps in the future. She'll then head back to town. Proceed a little further to the west and you'll encounter another landmark, Fish Rock. Normally, landmarks hold items or rupees that have to be obtained by touching them. In this case, the landmark holds a special item: a Fairy Doll. Get it and draw Fish Rock on the map.
Now head back to the field. You'll notice various enemies wandering about. Every enemy in the game holds specific items that have to be obtained by killing them. The more enemies you fight at once, the better and more the items and rupees they drop will be. However, fighting yourself also causes you to lose an amount of rupees depending on how long the fight lasts, how tough the enemies you fight are and with how many they are. These enemies won't be much of a problem though. Kill two rats at once to get three Bones. Return to your house again and try to make Tingle Fireworks in the Cooking Pot. Cooking is done by making all ingredients disappear by touching them a couple of times before the time runs out. Fill your Bottle with the Tingle Fireworks and leave your house. Now head all the way east and enter Port Town. To enter, you'll have to pay the Guard (5 rupees).
You'll notice most of the town is empty right now. It will get more crowded as you progress through the game. For now, keep walking and ignore the fountain. On the second screen, pay the Chef 10 rupees and the Armourer 15 rupees. Sell the Armourer the Tingle Fireworks to be able to buy a new Bottle for 50 rupees. Keep walking to meet the Town Map-Seller again. Show the map to her to receive 150 rupees (50 rupees for drawing Fish Rock and 100 rupees for completing the map). You can buy the map back for 125 rupees (this is recommendable eventually, but can be ignored for now). Keep walking to reach a third screen. This third screen is where eventually all the children of Port Town, to whom one or more quests or sidequests are connected, can be found. There also is a tree with three birds here. Every time you climb the ladder when there are birds in the tree, they'll fly away and leave a certain amount of rupees. This amount will get better as you progress through the game. For now, there's only one child here, Chiko, crying because she lost her "Fairy". Give her the Fairy Doll. She'll thank you and ask you to come to the statue of the town's hero Lyphos before running off. Do as she asked. You'll be stopped on the second screen by Chiko's Mum who wants to reward you for helping Chiko. Rewards are a delicate part of the gameplay. Whenever you help someone, you'll be offered a reward. This reward, like everything else, has to be estimated. Ask too much and you will get nothing. Ask too little and you'll miss out on a great opportunity for some extra cash. For now, ask 60 rupees from Chiko's Mum and leave town. Head north and go up the stairs. Follow the road to the statue and touch it. A voice will come from the statue, turning out to be Chiko who has managed to find a way into the dungeon under the statue. When she's gone, enter the dungeon.
 Hero's Shrine
The first thing you'll notice is a big, green guy who seems to be avoiding you at all cost. Ignore him and head to the entrance. You'll have to pay 50 rupees in order to enter Hero's Shrine. Proceed and you'll see the green guy running into the dungeon as well. Continue and you will see a skeleton that upon inspection will make it very clear once more how important rupees are. On the next screen, there are two vases. Vases always hold money and respawn after you've left the dungeon. Just approach them and touch them. Keep walking and you'll see a floor-button and two ways to go; one to the right and one down. The floor-button closes or opens the gate, so ignore it since that gate already is open. Head right to find another floor-button. Step on it to open the room. Do not take the rupees (95) on the altar. Instead, head to the skeleton and examine it to receive 5 rupees. You see, this room is a trap. If you pick up the rupees on the altar, the door will close and stay shut until you put 100 rupees on the altar. Leave the room with the 5 rupees from the skeleton and take the route down. Go down the stairs and notice the huge floor-buttons on your right. Walk a little further to see the greey guy again. Head down the stairs and go left. Talk to the green guy. His name is Teddy Todo and he'll be the first bodyguard you'll hire. Offer him 20 rupees to get him to follow you. Return to the big floor-buttons. First step on one of them with Tingle and then command Teddy to step on the other (touch him, then the button). Keep walking and you'll get into a small "arena" fight with two shadows. Defeat them to continue. The next room is filled with spike traps (8 rupees per hit), but to keep things easy (this is the first dungeon), their exact positions are shown on the map. To easily navigate through them, only look at the map on where to walk. In the next room, take the right route up and step on the floor-button to open the gate. Ignore the gate for now and continue down the hall to find a treasure chest containing 78 rupees. Head back and go through the gate. Ignore the passage to the left and go up. This room also is filled with spike traps, so navigate through them using the map. At the end is a Trick Chest. Pay it 50 rupees to receive 200. Go back, go left and keep walking. You'll end up in an "arena" fight in a room with spike traps. Defeat the shadows here to proceed. Continue to find a shadow guarding a big gate. Defeat it to open the gate and gain access to the big treasure chest. Enter it to confront Hero's Shrine's boss.
Beetle Lord Death Bug
- Beetle Lord Death Bug has to be beaten by dropping three bombs on his head. Pick them up and drag them to him. If you aren't fast enough or get hit by either the larvae or the energy balls Death Bug produces, the bomb explodes and you'll lose a few balloons. If all your balloons have popped, you lose and have to try again.
If you win, you and Teddy have a limited time to pick up all the Rupees Death Bug left. Contrary what it may look like, bodyguards don't steal items or rupees. Whatever they pick up ends up in Tingle's possession. The maximum you can get for defeating Death Bug is 1000 rupees. You'll also get your first Super Rupee, Metal.
You'll be automatically transported outside. Help Teddy free himself by paying him 100 rupees. Head to the Western Pool and donate 650 Rupees to get the Tower to grow. Note that you already donated some money in the beginning of the game and that that counts towards a total. So you'll only have to donate 650 rupees minus what you already donated. Uncle Rupee will appear and congratulate you with your first success. He'll tell you to go to the other side of the pool. From there, leave to Sunshine Seashore.