In the bowl of an electric mixer fitted with the paddle attachment beat the cream cheese, ½ cup of the confectioners’ sugar, cherry syrup and vanilla until completely smooth.
In a small microwave safe bowl, add the water and sprinkle the gelatin over the top evenly. Allow to sit for 1 minutes. Place the bowl in the microwave and microwave for 30 seconds. Remove and whisk until gelatin has dissolved completely. Set aside to cool to room temperature.
In another bowl, whip the cream until soft peaks form. Add the remaining ¾ cup confectioners’ sugar and continue to whip until stiff peaks form. Reserve about ½ cup of the plain whipped cream and place in the refrigerator for garnish.
With the cream cheese mixture still on the electric mixer, add in the gelatin mixture and beat until combined. Remove bowl.
Gently fold in ½ of the whipped cream until just combined. Fold in the remaining whipped cream and place in the refrigerator while preparing the crust.
Combine the graham cracker crumbs, granulated sugar and melted butter in a bowl until a sand-like consistency is formed.
Divide the crumb mixture amongst the bottoms of your chosen serving cups.
Remove the cheesecake mixture from the refrigerator and spoon it into a large piping bag. Cut the tip of the bag and pipe the mixture on top of the crust, dividing evenly amongst the cups. Add a dollop of plain whipped cream to each and top with a maraschino cherry. Place back in the refrigerator for at least one hour to allow to set completely. Serve chilled.