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1
For the caramelized sugar syrup: Place the sugar in a medium-size heavy skillet (not iron), set over moderately low heat, and allow to melt and caramelize to a rich golden brown.
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2
Do not stir the sugar as it melts but do shake the skillet from time to time.
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3
Add the boiling water, stirring briskly to dissolve the caramelized sugar.
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4
Simmer uncovered 8 to 10 minutes until the consistency of maple syrup.
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5
Reserve 2 tablespoons of the caramelized syrup for the flan; pour the balance into a chilled, well-buttered, shallow fluted 2-quart mold.
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6
Set the mold in the freezer while preparing the flan.
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7
For the flan: Preheat the oven to 325 degrees F. Combine the half-and-half, heavy cream, and sugar in a large heavy saucepan; add in the orange zest and bring to a simmer over moderately low heat, stirring now and then; blend in the 2 tablespoons of reserved caramelized syrup.
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8
Beat the egg yolks until frothy; blend 1 cup of the hot cream mixture into the yolks, stir back into pan, and heat, stirring constantly for 1 minute, until it lightly coats the back of a spoon.
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9
Remove from the heat and mix in the Port.
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10
Strain all through a fine sieve, then pour into the prepared mold.
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11
Set the mold in a shallow baking pan and pour in enough hot water to come halfway up the mold.
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12
Bake uncovered for 1 1/2 hours, or until a toothpick inserted near the center of the flan comes out clean.
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13
Remove from the oven and the water bath; cool for 1 hour, then refrigerate for 4 to 5 hours until firm.
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14
To invert the flan, dip the mold quickly in hot water, then turn out on a dessert plate with a turned up rim; the caramel syrup will come cascading down over the flan.
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15
Don't worry if the flan cracks, it will still be creamy and luscious.
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16
Cut into slim wedges, if possible, or scoop out, and serve.
