Since wine and whiskey are both strong components on their own, you might not think to mix them, but when paired, the two create a smooth, flavorful cocktail.
As for combinations, you could try an oaky bourbon with a sweet white like Riesling or Moscato to create a drink with notes of vanilla and caramel balanced by citrus.
For a richer, dynamic cocktail, pick reds like Shiraz or Cabernet Sauvignon which have the tannins to balance out a spiced rye or Scotch for a smoother finish.
You could also get fancy and mix sparkling wine with whiskey, or try cocktails like the Wine Old Fashioned, a spritz with whiskey and wine, or even a whiskey sangria.