Add 1 cup of the water and the sugar to a small saucepot over medium heat. Stir constantly until the sugar is dissolved, about 5 minutes. The liquid will be clear. Allow the simple syrup to come to room temperature.
Allow the simple syrup to come to room temperature.
Add the lemon juice, remaining water, pineapple juice, cream of coconut, and the cooled syrup to a large bowl.
Whisk to combine. Chill before serving.
Serve over ice, giving it a good stir before pouring as the liquid will separate. Garnish with cherries or as desired.
Notes
The simple syrup can be made ahead of time, allowing you to whisk up the lemonade whenever you're ready. You can also buy pre-made simple syrup at the store if you prefer, but it's SO much cheaper to make it at home.
Store any extra in the fridge for up to 3 days, being sure to stir well before serving.