Put first 5 ingredients (through Aperol) into a shaker filled halfway with ice. Shake vigorously for 10-15 seconds. Muddle basil; add to mixture in the shaker and shake for an additional 5-10 seconds.
Fill a glass with pulverized or crushed ice. Strain the contents of shaker over ice. With a spoon, top mixture with your desired amount of red wine so that it will “float” on top of the ice.
Optional: Take the hollowed out orange half, dry out thoroughly, and fill with high-proof rum, such as Cruzan 151. Push down into cocktail until the lower half of the orange is submerged; light the rum on fire with a match or lighter. For best results, you may want to soak a crouton or piece of bread in the rum.
Note: The last two ingredients listed, along with the entire third step of this recipe, is completely optional. This is simply an explanation of the method we used to create a flaming version of this cocktail for show; this step is in no way necessary to create a delicious beverage.
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