In a mixing bowl, whisk together heavy cream, whole milk, granulated sugar, and vanilla extract until the sugar is dissolved. Pour the mixture into an ice cream maker and churn according to the manufacturer's instructions until it reaches a soft-serve consistency. Transfer to an airtight container and freeze for at least 4 hours or until firm.

Prepare the Hot Cherries

In a saucepan over medium heat, combine cherries, sugar, and water. Cook, stirring occasionally, until the cherries are heated through and the sugar has dissolved, about 5-7 minutes. Remove from heat and set aside.

Make the Whipped Cream

In a mixing bowl, beat heavy cream, powdered sugar, and vanilla extract with an electric mixer on high speed until soft peaks form. Be careful not to over-whip.

Assemble the Dessert

Scoop the vanilla ice cream into bowls, top with hot cherries, and finish with a generous dollop of whipped cream.