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1
Preheat the oven to 250F, select one or two baking sheets large enough to arrange the tomatoes in one layer and brush with oil.
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2
Arrange the tomatoes on the sheets cut side up and sprinkle them lightly with salt.
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3
Set aside.
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4
Select a heavy roasting pan or large gratin dish for the fennel (it does not have to fit in a single layer), and brush the bottom with oil.
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5
Remove any fennel fronds and set aside for garnish.
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6
Cut the top stalks from the fennel and reserve for stock.
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7
Trim the base, and quarter each bulb, top to base.
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8
Discard any tough or bruised outer layers.
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9
Slice the quartered bulbs 1/4 inch thick, leaving the core as intact as possible to hold the layers together.
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10
(This wont be possible with all of the slices.)
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11
Set in the roasting pan, seasoning lightly with salt and drizzling with olive oil as you go.
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12
Cover the pan tightly with foil.
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13
Bake the tomatoes until collapsed and shriveled, 2 to 2 1/2 hours.
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14
(For the first hour or so, it will look like nothing is happening.)
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15
At the same time, bake the fennel until tender and easily pierced with the tip of a paring knife, 1 1/2 to 2 hours.
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16
(Once the fennel is tender, you can roast it uncovered to brown it and achieve a more intense flavor.)
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17
To serve, arrange the fennel and tomatoes decoratively on small plates and drizzle with extra-virgin olive oil.
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18
Finely chop the reserved fennel fronds and use them as a garnish.
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19
If you wish, dot a few drops of Balsamic Syrup decoratively around the plate.
