In a food processor or high-powered blender, combine pitted Medjool dates, coconut milk, vanilla extract, bourbon (if using), and a pinch of salt. Process until completely smooth and spreadable, about 5-10 minutes, scraping down the sides as needed. Add more milk 1 tbsp at a time if too thick. The caramel should be thick but easily spreadable.
Line a baking sheet with wax or parchment paper. Insert twigs or wooden sticks securely into the tops of the apples.
Prepare your desired toppings (brown rice krispies, chopped peanuts) so they are ready to press onto the apples.
Working one apple at a time, use a butter knife to spread the date caramel evenly over the bottom and sides of each apple.
Gently press your chosen toppings all around the caramel-coated apple. If using melted dark chocolate, you can drizzle it over the apple or dip the bottom half into the chocolate.
Place the finished apples on the prepared baking sheet. Sprinkle with flakey sea salt if desired. Refrigerate for 20-25 minutes, or until the caramel and chocolate are set.