Place at least 32 cups on two large rimmed sheet pans, making sure to not overlap the rims. Have extra cups ready just in case.
Place jello packets in a large heat proof measuring cup. Add the boiling water and whisk to dissolve. Whisk in the vodka.
Working quickly, pour the mixture into each cup, filling about ¾ of the cup. Allow to cool for a few minutes, then place lids on each cup. Refrigerate for at least 3 hours, or until completely cooled and set.
Arrange jello shots on a serving platter. Cut the bottom ¼ off 32 gummy bears, place each bear inside a peachy ring. Place a gummy garnish on each cup. Decorate with umbrellas graham cracker crumbs and chewy ribbons, if using.