Add pumpkin, cloves, cinnamon, nutmeg, star anise, vanilla, sugar, and 1 cup water into a four quart saucepan and simmer over medium heat, stir occasionally, until pumpkin is tender, about 45 minutes. Allow to come to room temperature, add the bottle of FitVine Cabernet Sauvignon and refrigerate at least 6 hours or overnight.
Mash pumpkin gently and place a fine-mesh sieve inside a large saucepan. Strain pumpkin mixture through sieve, discarding all solids. Rewarm till just heated through, serve in glass mugs garnished with a cinnamon stick.