In a medium bowl, stir together softened vanilla ice cream, chopped bacon, maple syrup, and mashed banana. Stir quickly until all of the add-ins are thoroughly combined. Add in the peanut butter and stir just enough to swirl the peanut butter throughout the ice cream.
Cover with plastic wrap and place in the freezer to reharden for 4 hours, or overnight.
To assemble, soften the ice cream just slightly and use a small ice cream scooper to scoop a heaping tablespoon of ice cream onto the bottom side of a butter cracker. Top with another butter cracker and place on a parchment lined cookie sheet. Continue until all the ice cream is gone and quickly place the assembled ice cream sandwiches in the freezer. Freeze for 2 hours before dipping.
While the sandwiches are re-freezing, melt chocolate and coconut oil over a double boiler until smooth and combined. Place the chocolate in a small (but not shallow) bowl.
Remove the frozen sandwiches from the freezer and dip half of the cracker sandwich into the milk chocolate. Shake of excess chocolate and place back on the cookie sheet. Sprinkle with sea salt and return to the freezer to harden the chocolate after all of the sandwiches are dipped.
Once the chocolate is hardened, sandwiches can be stored in a freezer-safe bag.