Salted caramel is an inherently perfect food, combining equal parts sweet and salty for a completely crave-worthy flavor experience. But it gets even better with this pie, which employs Colavita Extra Virgin Olive Oil to create one of the most luscious, fascinatingly flavored salted caramel fillings you’ve ever tasted. But that’s not all: it’s then topped with a rich, flavorful olive oil ganache made with chopped and melted Perugina dark chocolate, and then topped with coarse sea salt. All served atop a crunchy cookie crust, this pie is a study in delicious contrast, and perfect for chocolate and caramel lovers. This is truly a wow-worthy dessert, and bound to become a frequently requested item!
Preheat the oven to 350°F. Generously grease the pie plate on the bottom and sides with olive oil.
In a large bowl, mix the cookie crumbs, olive oil, and salt until it is a cohesive, evenly moistened mixture. Gently press the mixture into the greased pie plate, making sure to press the mixture evenly and firmly into the bottom and up the sides of the pan.
Place the pie plate in the preheated oven, and bake for 10 minutes, or until there is a slight matte look to the crust and it is fragrant and toasty-smelling. Remove from the oven and set to the side to cool completely.
Increase the oven heat to 425°F. Now, grab either a 9×9 or 9×13-inch baking plate. Have nearby your roasting pan or slightly larger pan, in which the smaller pan can comfortably fit with clearance on all sides.
Pour the sweetened condensed milk, vanilla extract, and salt into the baking pan. Give it a light mix to combine everything–it won’t come together in a smooth, creamy and cohesive mixture, but that is OK for now. Give the ingredients a few stirs for even distribution, then add the brown sugar and give it another stir. Once again, combining everything into a smooth mixture isn’t important right now.
Place the pan with the sweetened condensed milk inside of the larger vessel, and slowly pour water in the larger vessel until it reaches about halfway up the smaller baking pan. Pour along the side so that none of the water gets into the sweetened condensed milk mixture (although it is not going to ruin the recipe if a little splash of water gets into the mixture). It’s better to do this with the smaller pan already in the larger pan, because you don’t have to worry about sloshing due to water displacement.
Place a sheet of foil on the top of the baking pan with the condensed milk mixture. Leave it loosely wrapped as you will need to access the mixture throughout the baking process.
Very gently place the entire bulking mass into your preheated oven, taking care not to let the water spill.
The mixture will bake for two hours total, but you will require some mixing during the process. At 40 minutes, remove the mixture from the oven, lift the foil, and give the mixture a stir (you’ll see it starts to look more “mixed” at this point, although it may be somewhat bumpy or separated). Check the water level and replenish if needed. Place the pans back in the oven.
In 40 minutes (this is 80 minutes into the baking process now), repeat the previous step. Place the pans back in the oven.
Once your 120 minutes have passed, turn the oven heat off, but leave the mixture in the oven for about 20 more minutes. Remove from the oven, and gently remove the pan of condensed milk. Place it on a heatproof surface, and gently stir the mixture. It may still have some bumps and lumps but it will mostly dissipate as you mix. Once mostly smooth (a little bit of texture is fine), pour into the prepared pie shell. Let the mixture set completely at room temperature (this can take up to 2 hours) before completing the next step.
Once the caramel has set (you can test it by tilting the pan; the mixture should stay put), make your olive oil ganache topping. In the top of a double boiler, melt the chocolate. Once melted, remove from heat and stir in the olive oil until the mixture is silky and smooth.
Pour the chocolate ganache over the caramel layer. Sprinkle with coarse sea salt if desired.
Refrigerate the pie for several hours, or until ready to serve. While the pie is eatable right away, it will be sticky and a little messy when cut. Refrigerating will ensure that everything “sets”, giving the pie an easier texture for cutting and serving.