Best I could find for an 'Umbrella-y drink'

Umbrella Man Special recipe

Scale ingredients to servings
6 cl Absolut® vodka
6 cl Kahlua® coffee liqueur
6 cl Bailey's® Irish cream
6 cl Grand Marnier® orange liqueur
6 cl Drambuie® Scotch whisky

Mix all ingredients in a shaker. Serve with straw and ice cubes, put a cocktail umbrella beside the straw in the glass.
... although, I always considered an Umbrella-y drink to be something sickly sweet in a coconut with half a fruit salad inside and an umbrella and/or other garnishees.

Dr.Goodnow -- Refill on the Martini with extra olives ... but I'm not sure what to get for Jas - maybe some fancy juice slushie with an umbrella?