Gather everything in the equipment and ingredients lists.
Use your ice to fill the shaker almost to the top.
Pick up the vanilla vodka. Use the jigger to measure 1.5 oz. Dump that into the shaker.
Pick up the pineapple juice. Use the jigger to measure 1.5 oz. Dump that into the shaker.
Put the shaker lid over the top of the shaker.
Shake it well for about 15 seconds.
Remove the shaker lid.
Put the strainer over top of the shaker.
Pour the shot into the glass.
Pick up the grenadine. Use the jigger to measure .5 oz. Slowly pour that directly into the glass so that it sinks to the bottom.
If you want to add a garnish, stick a few maraschino cherries on a cocktail pick and pop it into the glass. Or cut a slice of pineapple and place it on the rim of the glass.