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1
Preheat the oven to 350 degrees F.
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2
Arrange the bread cubes on a baking sheet and lightly toast in the oven, about 10 minutes.
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3
Let cool.
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4
Increase the oven to 400 degrees F.
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5
Remove the cores from the top of the tomatoes and cut the top off the tomato 1/4 of the way down.
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6
Reserve the tops.
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7
Slice enough of the bottom off each tomato, so it stands up, but don't cut through to the seed.
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8
(If you cut too deep, patch the hole with the piece you have just sliced off, by placing it in the bottom after you've hollowed it out.)
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9
Using a melon baller, carefully scoop the inside of the tomatoes out, taking care not to penetrate the sides and create holes.
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10
Collect the balls of pulp and chop coarsely.
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11
Press the juice and seeds through a strainer.
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12
Add the strained juice to the chopped pulp.
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13
In a bowl, mix together the tomato pulp, Parmesan, olives, olive oil, parsley, basil, oregano, and garlic.
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14
Toss with the bread cubes and season with salt and pepper.
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15
Let the mixture sit until the bread cubes have soaked up most of the moisture.
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16
Season the interior of each tomato with salt and black pepper.
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17
Stuff each tomato with 1 bread cube and as much as herb olive mixture that you can pack in.
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18
Top with the reserved tomato tops and stick a toothpick through the center of the top to keep it from sliding off while it bakes.
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19
Place the stuffed tomatoes in a roasting pan that has been drizzled with olive oil.
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20
Drizzle the tops of tomatoes with olive oil and season with salt and pepper.
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21
Roast until bubbling and tender, about 30 to 40 minutes.
