Lightly oil an 8 x 8 inch pan then measure and cut a piece of parchment paper that will fit inside the pan and come up the sides by at least 1 inch. Next, lightly oil the parchment paper and place into the pan. Set the pan aside.
Place the sugars, heavy cream, butter, corn syrup and bourbon in a deep skillet or Dutch oven. Place over medium heat and attach a candy thermometer to the edge of the skillet with the tip touching the ingredients.
Bring to a boil, stirring occasionally and then reduce to medium-low. Allow the mixture to simmer until it reaches between 238°F and 245°F. The lower the temperature the softer the caramel. The moment it reaches your desired temperature, remove from heat and stir in the vanilla extract.
Carefully pour the caramel into the prepared dish and allow to cool for 4 hours.
Once the caramel is hard, unmold it. If it is too soft to work with, place in the refrigerator for 30 to 45 minutes to help it firm up. Then use a knife to cute into 1 x 1 inch squares.
Line a baking sheet with parchment paper. Chop the chocolate into fine pieces add 2/3 of it to a microwave safe bowl. Microwave in 30 second intervals, stirring in between until the chocolate has melted. Add the remaining chocolate and stir until it is smooth and shiny.
Use two forks to dip each caramel into the melted chocolate then place onto parchment paper. Sprinkle a little salt on top and allow the chocolate to set.