In a bowl, muddle the strawberries and olive oil together. Let this sit for 5 minutes to let the strawberries release their natural juices.
In a cocktail shaker, add the aperol, amaro, bourbon and lemon juice. Fill up with ice and shake for 30 seconds.
To a lowball glass, add the strawberries and a large ice cube. Pour the drink over top and drizzle with any remaining strawberry & olive oil left in the bowl.
Enjoy ice cold, preferably on a hot day :)