Using a funnel, add the bourbon, Amaro Nonino, fresh lemon juice, Aperol, spiced cranberry syrup, and filtered water to a freezer-safe bottle.
Seal tightly and gently shake or invert the bottle several times to combine.
Place in the freezer for at least 4–6 hours, or until thoroughly chilled.
When ready to serve, give the bottle a gentle shake and pour approximately 3–4 ounces into a chilled coupe or Nick & Nora glass.
Garnish with an orange twist or fresh cranberries, if desired, and enjoy!