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Grease an 8x8 inch pan with oil. Line with parchment paper and grease parchment also.
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Combine brown sugar and water in a medium saucepan and stir together well. Wipe down the side of pan with a wet spatula or pastry brush to make sure there are no sugar crystals stuck to the side. Place pan over low heat and bring the mixture slowly to a boil and cook for 8 to 10 minutes without stirring until it the syrup starts to darken and smell caramely. It should read somewhere between 270°F to 300°F on a candy thermometer.
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While your syrup is boiling gently, mix the salt and cream in a separate small saucepan and place over medium heat. Stir until steaming and then set aside.
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Once your syrup is ready, turn off heat and carefully pour in cream mixture (it will bubble). Stir gently, then return to heat and bring mixture back to a boil until it reaches 245°F to 250°F.
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Remove from heat and stir in vanilla quickly, then pour caramel into prepared pan.
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Allow the caramel to cool and set for at least 3 hours or overnight. Once set, cut them into small squares. Melt chocolate in a double boiler and dip caramels to coat then place on wire rack to allow excess to drip off. If desired, sprinkle with sea salt then allow chocolate to dry.