Dragon Roost Island is home to the Rito, a tribe of birdlike humanoids whose duty is to deliver mail to all islands of the Great Sea. Valoo, a great red dragon, also makes his home at the top of Dragon Roost Island. You access Dragon Roost Cavern dungeon from this island, and many other important plot points occur here as well.
Beedle’s Shop Ship
Enter Beedle’s Shop Ship, which slowly sails around this island, to purchase Hyoi Pears for 10 Rupees, All-Purpose Bait for 30 Rupees, and 30 bombs for 60 Rupees.
Wind Waker
You receive the magical baton, the Wind Waker, from the King of Red Lions as soon as you land on Dragon Roost Island for the first time. For more information, refer to the walkthrough.
Empty Bottle #1
Medli gives you an Empty Bottle just before she darts into the Dragon Roost Cavern. For more information, refer to the walkthrough.
Grappling Hook
Medli also gives you the Grappling Hook after you free her from her holding cell in the Dragon Roost Cavern. For more information, refer to the walkthrough.
Wind’s Requiem
During your first visit to Dragon Roost Island, head to the Wind Shrine on a small nearby isle. One of the Wind Shrine’s two stone tablets has been broken; the other has three mysterious symbols etched into it.
Pull out the Wind Waker and play along with the symbols scribed onto the unbroken stone tablet to learn the “Wind’s Requiem.” This song has the power to dictate the direction of the wind. To play it, push 
, 
, 
while using the Wind Waker.
Silver Rupee (via Treasure Chart #39)
Find and open Treasure Chart #39 (found inside the Dragon Roost Cavern dungeon at Dragon Roost Island [F2]) to pull a chest from the Great Sea near Dragon Roost Island. The chest contains a Silver Rupee.
Orange Rupee
You must have the Deku Leaf to get this Orange Rupee. Walk along the inside balcony on the second floor of the Rito Aerie and exit through the second doorway.
Position yourself as shown in the screenshot, right where the Rito was standing. Use your Hero’s Bow (if you’ve found it) to take out the Kargoroc nesting in a rock spire ahead of you. Direct the wind by conducting the “Wind’s Requiem,” and use the Deku Leaf to reach the top of the distant rock spire ahead to find a stone tablet. The tablet tells you to proceed forward.
Again, set the wind and use the Deku Leaf to float around the first rock spire directly ahead of you, then swing back and safely land on top of another rock spire with a second stone tablet. This tablet tells you to go left. First, use the Boomerang to take out the nearby Kargoroc.
Look to the grassy ledge to the left, then set the wind blowing in that direction with the “Wind’s Requiem.” Use the Deku Leaf one last time to reach the grassy ledge, and then run up the trail along the side of the cliff. Inside you find a chest containing an Orange Rupee.
To get out, push the block ahead until it falls out of the side of the cliff, then jump down.
Piece of Heart #5 (via Mail Sorting)
Talk to Koboli, the Rito who works behind the counter at the Mail Center on the second floor of the Rito Aerie, to play the Mail Center minigame. You must sort each piece of mail into its corresponding slot in 30 seconds.
First, sort 10 envelopes in 30 seconds. Then sort 20 letters or more in the same amount of time, and you’ll be given a raise. If you manage to achieve that goal, you’re then asked to sort 25 letters, still in only 30 seconds. Do that and Koboli is stunned. He showers you with compliments and gives you another increase in pay.
Memorize the patterns on the mail slots so you don’t even have to look at them to know where each envelope belongs. However, this is mostly a game of luck. Sometimes you get a streak of several envelopes of the same type. This gives you a much better chance of sorting out 25 letters within the 30 seconds. Just keep trying until you get lucky!
Once you’ve proven your skills at letter-flicking, exit the aerie. Turn around and go back inside, and return to the Mail Center. Baito, the new part-timer, is working behind the counter.
Talk to Baito, and he tells you how much he’d love to see you sort 25 letters like you did before. Do so, and Baito is so impressed that he asks you to mail a letter to his mom for him. Drop the letter in the postbox outside, near the aerie entrance.
Don’t worry—you have some nice rewards coming your way. For helping and impressing Baito so much, you receive two letters in the mail the next day. One letter is from Baito and one is from his mother, Kashiko. Baito’s letter comes with a Red Rupee, and attached to Kashiko’s letter is Piece of Heart #5. You can play the Mail Center minigame again anytime by talking to Koboli.
Piece of Heart #38
One of the Rito guards who stands watch on the second floor of the aerie happens to have a girlfriend who adores Golden Feathers. As soon as you’ve collected 20 or more Golden Feathers, show them to the Rito guard. He’s more than happy to take 20 off your hands and gives you an Orange Rupee in return. Check any postbox the next day to find a letter from his extremely grateful girlfriend. Attached to the letter you find Piece of Heart #38.
Purple Rupee (via Secret Cave)
Head to the Wind Shrine on a small isle near Dragon Roost Island, and look for a large, gray boulder on the beach. Bomb the boulder to reveal a hole leading into a Secret Cave. Drop into the hole and enter the cavern.
This Secret Cave isn’t too difficult. Enter each room and defeat every enemy you find (mostly ChuChus). A torch above each door lights as you clear out the room. When all four torches are lit, a final door unseals. Enter it to find a chest containing a Purple Rupee.
Silver Rupee
A curious sign near the Bomb Plants outside Dragon Roost Island shows an arrow pointing upward. Look at the side of the cliff to discover the sign’s significance: A long line of Bomb Flowers grows from the side of the cliff high above you, and they seem to be leading straight up to a gray boulder.
Using the Hero’s Bow, fire an arrow at the first Bomb Flower in line. The Bomb Flower flashes for a second before exploding, setting off a chain reaction that destroys the gray boulder. A chest drops from the sky and lands near the sign—it must have been sitting on top of the boulder! Open the chest to find a valuable Silver Rupee.