Moisten the rim of the martini glass with a slice of key lime. Swirl the rim in crushed graham crackers. Set aside.
Pour the vanilla vodka, key lime juice, pineapple juice, simple syrup and heavy cream into a cocktail shaker.
Add ice. Secure the top on the cocktail shaker. Using two hands, shake the mixture vigorously for about 15-30 seconds.
Remove the top from the cocktail shaker. Grab that graham cracker-rimmed garnished glass and strain the drink.
If a boozy key lime pie in a cocktail glass sounds like your kind of happy hour celebration, shake up a round of this delicious martini. Cheers!