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I make them muddled for guests that do not like straight bourbon. I gently muddle a cherry in the serving glass, add syrup, bitters and stir. Add a shot of bourbon and ice, stir. I may stop here and serve if they do not want it too strong. Otherwise I had a half shot or so of rye whiskey (or more bourbon). Orange peel squeezed and then rubbed on the rim. Garnish with the orange peel and another cherry. I only muddle orange when requested, and then I prepare outside of the serving glass.
I used store bought pineapple juice which was quite sweet (no added sugar though) and it masked the vodka more than most flavored martinis. That can be good since some do not like the vodka taste. I liked the Chambord in it.
Made with Hangar 1 vodka and Revolution Chocolate and Coffee liquor. I was surprised that the vodka was so prevalent. I expected the espresso to overpower. It is more like a martini than I expected. I will try some other favorite vodkas, do not be afraid to use the good stuff as it will shine through.