In a large bowl, combine popped popcorn and peanuts. Set aside. Preheat oven to 325F and line 3 baking sheets with parchment paper. Set aside.
Bring butter and honey to a boil over medium-high heat. Stir until caramel is thickened and golden. Remove from heat and whisk in cream, salt and vanilla.
Pour warm caramel sauce over popcorn-peanut mixture and stir until evenly coated. Divide popcorn mixture between prepared baking sheets. Bake caramel popcorn at 325F 20-25 minutes until golden, stirring once.
In a double-boiler, melt chocolate chips and oil until smooth. Drizzle melted chocolate over popcorn. Allow popcorn to harden and cool completely at room temperature. Once cooled, break popcorn apart and store.
Store popcorn in an airtight container at room temperature up to 1 week.