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1
Core tomatoes and cut in half lengthwise; arrange, cut side up, on foil lined rimmed baking sheet.
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2
In a small bowl, mix 2 tablespoons of the oil, garlic and half each of the salt and pepper; brush over tomatoes.
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3
Bake in 350u00b0F oven until softened and shriveled and bottoms are browned, about 2 hours.
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4
Meanwhile, trim fronds from fennel bulb and reserve; cut off stalks and discard.
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5
Cut fennel in half lengthwise.
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6
Trim out and discard core; cut fennel into 1/2 inch cubes.
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7
In large saucepan, heat 1 tablespoon of the remaining oil over medium heat; cook fennel, stirring occasionally, until golden, about 8 minutes.
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8
Add 1 1/2 cups water; reduce heat, cover and simmer until very tender, about 20 minutes.
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9
Pour into bowl.
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10
Add 1 tablespoon of the remaining oil into pan; cook onion over medium heat, stirring occasionally, until softened, about 5 minutes.
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11
Add tomatoes and stock; bring to boil.
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12
Reduce heat and simmer for 15 minutes.
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13
Transfer tomato mixture to blender or food processor; puree until smooth.
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14
Return to pan.
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15
Stir in cooked fennel, basil and remaining salt and pepper.
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16
(Make ahead: let cool and refrigerate in airtight container for up to 2 days.) Heat until steaming, about 5 minutes.
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17
In bowl, whisk vinegar with remaining oil.
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18
Ladle soup into bowls; garnish with drizzle of vinegar mixture.
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19
Arrange reserved fronds over top.
