Add the tomatoes, cucumber, celery, 3 cups of grapes and jalapeno to a blender and puree. Set up a sieve lined with cheesecloth over a large bowl and pour in the pureed mixture. Set the bowl in the refrigerator while it strains.
Once you have the extracted the liquid, remove it from the refrigerator. Add the horseradish, superfine sugar and 2 lime wedges to a pitcher and muddle with a wooden spoon. Stir in the extracted tomato juice, some crushed ice and a few splashes of vodka. Stir to combine.
Rub a lime wedge on part of the rim of each glass. Dip the rim into the salt and pepper mixture so it sticks to the wet part of the rim. Pour the drink into the glasses and garnish with cucumber spears, celery sticks and a few grapes.