To go with Orlando, I wanted something that would have both a masculine and feminine aspect to it, along with something to create some interested.
I flipped through some options on my Food & Wine cocktails app and came across the Timeless Modern. I was definitely intrigued by the name, and the ingredients looked different from anything else that I've tried on here.
2 thin lemon wheels
2 thin lime wheels
3 thin orange wheels
1 1/2 teaspoons maraschino liqueur
1/2 teaspoon grenadine
Dash of Angostura bitters
1 maraschino cherry
2 1/2 ounces bourbon
Set aside 1 wheel of each citrus fruit. In a cocktail shaker, muddle all of the ingredients except the bourbon and ice. Add the bourbon and ice and shake well. Strain into a chilled martini glass and garnish with the reserved citrus wheels.
I chose to change the recipe a bit and muddled all the ingredients and served the cocktail over ice in a rocks glass. Definitely a unique combination, but one that seemed to fit the book for me. The bourbon being the stronger masculine edge of things and the surprising lightness of the citrus fruits being the softer feminine side.