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1
Brush six 3/4-cup glass custard cups with canola oil.
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2
Pour milk into medium bowl.
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3
Sprinkle gelatin over; let stand until gelatin softens, about 5 minutes.
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4
Stir cream and sugar in heavy medium saucepan over medium-high heat until sugar dissolves.
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5
Bring to boil; remove from heat.
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6
Add chocolate; whisk until melted.
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7
Whisk warm chocolate mixture into gelatin mixture; stir to dissolve.
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8
Stir in vanilla.
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9
Working in 2 batches, transfer mixture to blender and use only 3 on/off turns to just fully blend mixture (do not overmix).
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10
Divide mixture among custard cups.
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11
Cover and chill 24 hours.
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12
(Can be made 2 days ahead.
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13
Keep chilled.)
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14
Stir cherries, Port, sugar, and vinegar in heavy large skillet over high heat until sugar dissolves.
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15
Bring to boil; reduce heat to medium and simmer until cherries are soft and wooden spoon leaves path in sauce when drawn across bottom of skillet, about 15 minutes.
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16
Remove from heat.
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17
Cool to room temperature.
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18
(Can be made 2 days ahead.
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19
Cover and refrigerate.
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20
Bring to room temperature before continuing.)
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21
Set custard cups in large baking dish.
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22
Pour enough hot water into dish to come halfway up sides of cups.
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23
Let stand 11/2 minutes.
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24
Take cups out of water; wipe bottoms dry.
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25
Invert each onto plate, shaking gently to dislodge panna cotta.
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26
Spoon cherries and sauce over panna cottas and serve.
