Caramel Simple syrup:
Over low heat, combine 1 cup of sugar and 1/4 cup of water in a small saucepan, stirring until all sugar is dissolved. Cover and boil for two minutes. Remove lid and boil, stirring occasionally, until syrup is a dark amber color. Remove from heat and carefully add 1/2 cup of water, splash of vanilla, and pinch of salt while stirring. Once everything is combined*, let cool and store in fridge.
*You may need to put it back over low heat after the additions to melt it again.
Three sage leaves
.75 oz. apple cider
.75 oz. caramel simple syrup
1.5 oz. Templeton Rye Whiskey
Muddle sage with a splash of cider. Add ice and remaining ingredients and shake until very cold. Pour into highball over ice and garnish with a sage leaf.