Line a cookie sheet or jelly roll pan with parchment paper and place in the freezer.

 

Place washed and dried maraschino cherries in a medium bowl and set aside.

 

In a medium stainless steel bowl placed over a small pot of simmering water, melt the semi-sweet chocolate and coconut oil until melted and completely smooth. Remove bowl from heat and allow the mixture to cool for 3-5 minutes.

 

Remove parchment lined cookie sheet from the freezer and set on your work surface.

Hold a maraschino cherry by the stem and dip, submerging cherry completely into the melted chocolate mixture. Lift the cherry from the melted chocolate and allow the excess to drain completely back into the bowl. Place the cherry on the cold parchment lined cookie sheet. Repeat with remaining maraschino cherries.

Place the cookie sheet in the freezer until the chocolate has set, about 7-10 minutes. While chocolate sets, make the caramel.

Thicken the heavy cream quickly by whipping it with either a small whisk or a fork. Fold into the dulce de leche and add vanilla extract. Transfer mixture to a piping bag with a small round tip. Place in the fridge until ready to use.

Remove cherries from freezer. Hold a maraschino cherry by the stem and dip, submerging cherry completely into the melted chocolate mixture. Lift the cherry from the melted chocolate and allow the excess to drain completely back into the bowl. Place the cherry on the parchment lined cookie sheet. Repeat with remaining maraschino cherries. Place the cherries on the parchment lined cookie sheet and place back in the freezer to set, another 7-10 minutes.

 

Once the chocolate has set, either pipe a mound of dulce de leche right above the stem of each cherry, or drizzle each cherry with caramel.