To make strawberry simple syrup, combine ½ cup sugar, ½ cup water, and 8 strawberries in a small saucepot. Bring just to a boil and then chill till no longer warm in refrigerator. Using a fine mesh strainer, strain syrup into a container and discard strawberries.
To make pickled blueberries, combine ¼ cup sugar, ¼ cup apple cider vinegar, and ½ cup water in a small sauce pot. Bring just to a boil and then pour over ½ cup fresh blueberries. Chill until cold.
To make strawberry coconut water, using a blender, blend together 1 cup coconut water and 5 chopped strawberries. Strain through a fine mesh strainer. Set aside.
In a cocktail shaker, combine rum, strawberry-coconut water, strawberry simple syrup, and fresh strawberries. Muddle until strawberries are broken up.
Add a few ice cubes and shake until well combined and cold.