Cloud 9 - 25 Dragonflies

Powder - there are 4 power sources for the hour glass and each of them has 3 power sources of their own and all 12 need to be hit by lightning.

Ice Rune From the start of the level, where you meet Powder, go straight across the bridge and get the ICe Rune

Turn left and glide to the island and take the whirlwind to the upper level. you should be able to see the machine from up here. Glide to the island below the machine and take the whirlwind up to the machine.

Machine #1

Thimble - Retrieve wand from thief

Machine #2

Dragonfly6 On the loose Savino Yellow

Dragonfly7 Pillar to Pillar Sylvia Green

Dragonfly6 Around the Way Iceboy Red

Machine #3

From the 3rd Machine you can take a moving platform to the upper level of the island with the magic whirlwind.

On the other side is another moving platform that goes down to a place with 4 Pillars. Just glide down there.

Take a left into a winding passage. As you exit the passage you will find winding stairs. Some people call these. "hidden stairs" because of a bug that causes them to disappear. Never happened to me.

Nimble - At the top of the stairs you will find a huge round pool. Nimble the bear will ask you to use the fire ball powerup to take care of some storm clouds. When they are gone talk to Nimble to get a Dragonfly.
Dragonfly3 Thunder Cloud Attack Takahiro Blue

Dive in the Pool and go through the tunnel. After you emerge from the water the 4th machine will be on an island to your right. There are a couple of tricky glides. You will need to do walking jumps and use hover(triangle) at the end.

Machine #4

Danny - He is standing in front of the Exit portal and he will give you the Dragonfly for powering the 4 machines. If he doesn't go back to each machine and see if there is a beam hitting the hour glass. Zap the generators again until there is.
Dragonfly4 Hourglass Challenge Rick Blue

The Building behind the Exit portal is the Clock Tower. Go through it to the other side where you will find a ladder. The ladder takes you to an upper room with Gears in it.

Dragonfly1 To Clock Tower Goose Red

Dragonfly5 Lip of the Clock Margaret Green

Last 14 Gems - The Gems are near the beginning of the level high up on a roof. Glide from the upper ledge of the clock tower, the building behind the exit portal. Make sure you go around the clouds and to the left of the orange dome.

Challenge Portal - Rainbow Speedway right above start point. To get there go straight across the bridge in front of you. turn left and glide to an island with a whirlwind. ride the whirlwind to the top. When up there turn around toward the start point and you should see a moving platform where you are and the platform above the start point. Ride it. The portal is in the back side of the dome.

Obstacles:

8 Rings

Fly through rings and they disappear

8 Jumping Stars

8 Go-Carts

they travel in endless laps around the course. land and hit SQUARE to start super charging. Go in the opposite direction as the gocarts.

8 Flying Bed Riptocs

they fly in endless laps. fly against them and flame each one.

Dragonfly8 Rainbow Time Trial Tashistation Blue

Dragonfly9 Rainbow Race Grayson Blue

Challenge Portal - Puffy Palace Portal Inside the Clock Tower

Pudgy - I guess being in his home has changed his voice?
Dragonfly10 Spitfire - Sky Base Tweedle Blue

Movie: Scattered