On medium heat, heat 1 cup sugar in a saucepan, stirring with a wooden spoon, until it melts and gets a dark amber color.
Carefully add 1 1/4 cups heavy cream and stir until all the caramel has dissolved. Transfer to a bowl and stir in sea salt and vanilla. Cool to room temperature.
In the same saucepan, bring milk, remaining cup of heavy cream, and remaining 1/4 cup sugar to a boil, stirring occasionally.
In a medium bowl, lightly whisk eggs then add half of hot milk mixture in a slow stream, whisking constantly. Pour back into saucepan and stir constantly with a wooden spoon. Cook on medium heat until custard coats back of spoon (do not let boil). Pour custard through a fine-mesh sieve into a large bowl. Don't skip this part, you don't want scrambled eggs in your ice cream, do you? Ew.
Stir in cooled caramel then place in the refrigerator for 3 to 6 hours, stirring every half hour or so.
After 3-6 hours, place the mixture into ice cream maker. Follow the directions of your ice cream maker.
Meanwhile, melt chocolate chips with coconut oil in a small bowl in the microwave for 30 seconds. Remove from microwave and stir. Add waffle cone pieces and make sure to get them all covered in chocolate. Set aside to cool/harden.
Once the ice cream is done, transfer it to an airtight container and fold in the chocolate covered waffle pieces. Place in freezer to firm up.