Brew 1 cup of strong coffee and let it cool to room temperature. Transfer to the refrigerator and chill for at least 30 minutes so it is completely cold.
1 cup strong brewed coffee
Place caramel candies or toffee bits in a small plastic bag and gently crush with a rolling pin or the bottom of a heavy pan until you have small crunchy bits. Stir in turbinado sugar if using and set aside.
2 tablespoons crushed caramel candies, 2 tablespoons crushed toffee bits or honeycomb candy, 1–2 tablespoons coarse turbinado sugar
Add heavy whipping cream, powdered sugar, and vanilla extract to a cold bowl. Whip with a hand mixer or whisk until soft peaks form. Do not overbeat. Refrigerate while preparing the frappuccino.
1/2 cup heavy whipping cream, 1 tablespoon powdered sugar, 1/4 teaspoon vanilla extract
In a blender, combine chilled coffee, milk, 2 tablespoons sugar or simple syrup, 1/4 cup caramel sauce, ice cubes, vanilla extract, and a pinch of fine sea salt. Add the liquid ingredients first if your blender struggles with ice.
1 cup strong brewed coffee, 1 cup milk, 2–3 tablespoons granulated sugar or simple syrup, 1/4 cup caramel sauce, 2 cups ice cubes, 1/4 teaspoon vanilla extract, 1 pinch fine sea salt
Blend on high for 30–45 seconds, or until the ice is completely crushed and the drink looks smooth and frosty. If it is too thick, add a splash of milk; if too thin, add a few more ice cubes and blend again.
Taste the blended frappuccino and add more sugar or caramel sauce if you prefer it sweeter. Blend again briefly to combine, keeping in mind it will get sweeter once topped with caramel and whipped cream.
2–3 tablespoons granulated sugar or simple syrup, 1/4 cup caramel sauce
Warm 1/4–1/3 cup caramel sauce for 10–15 seconds in the microwave until just pourable. Drizzle it along the inside of each glass, starting at the top and letting it run down the sides to create caramel ribbons. Add a little to the bottom of each glass if desired.
1/4–1/3 cup caramel sauce
Fill each prepared glass halfway with the blended frappuccino. Drizzle a small amount of caramel over this layer, then fill the glasses the rest of the way with more frappuccino to create hidden caramel pockets.
1/4 cup caramel sauce, 1/4–1/3 cup caramel sauce
Spoon or pipe a generous swirl of whipped cream on top of each drink.
1/2 cup heavy whipping cream, 1 tablespoon powdered sugar, 1/4 teaspoon vanilla extract
Drizzle additional caramel sauce over the whipped cream and sprinkle the crushed caramel candies, toffee bits, and/or turbinado sugar generously on top. Serve immediately with a straw and a spoon.
1/4–1/3 cup caramel sauce, 2 tablespoons crushed caramel candies, 2 tablespoons crushed toffee bits or honeycomb candy, 1–2 tablespoons coarse turbinado sugar