Fresh Orange Sherbet and an Embarrassment of Scotches

My in-laws have nice friends. Very nice friends, with very nice Scotch from the Scotch Malt Whisky Society that was a bit higher-proof than they prefer. 

I got a text asking if I might like to take it off of their hands. I agreed, since I'm nice like that, and because when someone asks if you want a case of free, limited edition single malt, you say "yes." I'm debating which of my treasured bottles of unicorn bourbon to send their way as a "thank you" – I'm struggling to select one that sufficiently conveys my gratitude that isn't already open. (I'm not so good at delayed gratification.)

So... I had some extra Scotch to work with. I also had leftover Negroni things from The Grand Ole (Concrete) Opry, and some orange juice after feeding my wife several mimosas on her desperately needed and very well-deserved day off.

Orange juice, Scotch, and vermouth/Amaro-ish things were starting to sound like a Blood & Sand. Inspired by the name of one of these lovely Scotches – "Fresh orange sherbet" – I decided to double down on the orange of the Blood & Sand and add in some vanilla.

For the orange, I swapped the Blood & Sand's Cherry Heering for Italicus' bergamot liqueur, and Hotel Starlino and smoked orange bitters for the sweet vermouth, which conveniently kept it from turning into a sugar bomb. Dark rum and a tiny bit of homemade vanilla extract (which is basically just vanilla-infused, high-proof bourbon, no?) took care of the vanilla flavors. (And yes, I broke into that bottle of vanilla early, but the fact that I made it this far is kind of a big deal – see above re: delayed gratification).

I'd put this over a large ice cube or sphere – I had none hand, so I went with smaller cubes. (Aren't you proud of me for at least using ice that is actually presentable, though?)
Fresh Orange Sherbet

1 part single malt Scotch (I was fortunate to have a bottle of the Scotch Malt Whisky Society's Fresh Orange Sherbet, which kinda tastes like it sounds)
1 part orange juice
1/2 part Papa's Pilar or other dark rum
1/2 part Hotel Starlino Orange Aperitivo or similar
Smoked (or not) orange bitters 
Vanilla extract
Orange wheel and maraschino cherries to garnish

Combine rum, scotch, aperitivo, orange juice, and vanilla in a shaker over ice and shake. Pour over a large ice cube or sphere in a tumbler. Garnish with orange wheel and cherries, and serve.