Combine cherries and sugar in a saucepan and toss to coat. Let macerate until juices flow, about 1 hour. Bring to a boil, then lower heat and simmer for about 10 minutes. Chill until cool.
Pour half and half and sugar into saucepan, bring to a boil. Beat egg yolks in a medium bowl. Whisk one cup of the hot cream into the egg yolks. Then gradually add the egg mixture - in a slow steady stream - back into the pan of half and half.
Stir over low-medium heat until custard thickens and leaves a path on the back of a spoon, about 4 minutes. Remove from heat. Mix in whipping cream and vanilla, refridgerate until cold.
Pour into the ice cream machine according to manufacturer's instructions. After about 20 minutes, add the cherry mixtures. Process about 15 minutes longer, then transfer to container and freeze.
I made a batch of chocolate wafers, these were very simple. No messy flour, just roll out the dough between two sheets of wax paper and cut them out.
You could do them rectangular like the old school ice cream sandwiches, but I thought round was cute.
**Don't forget to prick deep holes all over the cookie before baking! That's not just decoration, it let's the steam out so the cookie doesn't puff up...
Freezing the cookies after cooling for at least an hour, let's them stiffen up so they can be pressed.
You can buy a fancy press but I just used plastic wrap and my hands to shape them.
Now here's the finished product.
You can use any kind of ice cream, I made a batch of cherry and a batch of chocolate chip, but anything will taste great.