Peel bananas and cut into thick slices. Place in a zipper bag in a single layer. Freeze for 3 hours or until frozen solid.
Place bananas in a blender with half-and-half and vanilla extract.
Pulse blender for about a minute. Scoop blended banana at the bottom and mix unblended bananas toward the bottom. Repeat until the mixture is fully blended.
If you don’t own a cherry pitter, use a chopstick: remove the stem, and push through the stem end until the pit pops out. Chop cherries roughly.
Mix cherries into the banana mixture until evenly distributed.