Preheat waffle iron.
Combine flour, cocoa powder, sugar, baking soda, and salt.
In a microwave-safe bowl, combine milk and coconut oil. Warm in the microwave until coconut oil is melted (30 seconds to a minute). Whisk into flour mixture and add vanilla.
Once waffle iron is heated, pour on half the waffle mix, making sure it spreads nearly to the edge to the iron. Cook about 3 minutes or until the top of the iron separates cleanly from the waffle. Repeat with remaining waffle batter.
Separate waffles into four even pieces. Freeze for at least one hour.
In a food processor, pulse together bananas and most of the cherries (leave a few out to add in after). Add a splash or two of almond milk and blend until smooth and desired consistency is reached.
Roughly chop the remaining cherries and fold into nice cream. Transfer nice cream to a container and freeze for at least one hour.
Scoop nice cream onto a waffle portion. Top with another waffle portion and press down gently. You can use a butter knife to smooth out the sides. Repeat with remaining waffle pieces. Freeze the waffle sandwiches at least an hour before enjoying.