Here's two of my favorites:
The Godfather
2 ounces of blended Scotch whisky (I use Dewar's)
.5 ounces of Amaretto (I use Disaronno)
Shake ingredients in a shaker with ice. In a lowball glass, add one large ice cube. Pour contents into glass. Run the slice of an orange peel around the rim and then drop into drink as garnish.
I never had this drink before until my last night in Sicily. This is close, but then again I'm not in Sicily.
Second Circle
2 ounces of burbon wiskey
1 ounce of ruby port wine
1 teaspoon of maple syrup
2 luxardo cherries
Combine bourbon, port wine and maple syrup into a shaker with ice. Shake. Pour into a lowball glass (no ice). Drop cherries into drink.
I had a variation of this drink in Manhattan a few years ago and I have been chasing it ever since. This is a good nightcap.