This achievement is unlocked for finishing the Whirligig in Midday Gardens and travelling to Evening Lake for the first time. In order to complete the Whirligig you will need one character from each of the Midday Gardens worlds (except the speedway). In order to get each character you just have to run through each level to the end, you do not need to 100% the levels at this time. You will need the following characters:
Sgt. Byrd - Sgt. Byrd's Base (Pay Moneybags 700 gems)
Doug - Icy Peak (Already unlocked)
Jasper - Enchanted Towers (Hit the target above the portal to open)
Shiny - Spooky Swamp (25 eggs needed)
Sing Sing - Bamboo Terrace (30 eggs needed)
After completing the worlds, you will be automatically taken over to the Whirligig. Simply hop on and the achievement is all yours!