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1. Drizzle caramel topping in a zigzag design inside each of eight 5- to 6-ounce glasses. Drizzle chocolate ice cream topping into each glass. Arrange glasses on a tray; freeze until needed.
2. Butter a large piece of foil; set aside. In a large heavy skillet spread sugar in an even layer. Heat over medium-high heat until sugar begins to melt, shaking the skillet occasionally; do not stir. When the sugar begins to melt, reduce heat to medium-low and cook about 5 minutes more or until all of the sugar melts and is golden, gradually stirring the melted sugar into the unmelted sugar with a wooden spoon. With a spoon, immediately drizzle the melted sugar in eight circles (each about 3 inches in diameter) onto prepared foil, drizzling zigzags inside the circles to resemble webs. Quickly sprinkle each with salt.* Set aside until needed.
3. Just before serving, in a blender combine half of the ice cream, half of the milk, half of the 3 tablespoons caramel topping, and half of the 3 tablespoons chocolate ice cream topping. Cover and blend until smooth, stopping to scrape down side as needed. Pour ice cream mixture into four of the prepared glasses. Repeat with the remaining ice cream, milk, caramel topping, and chocolate ice cream topping. Top each with one of the salted-caramel webs.