2 lb tomatoes, cored, quartered
2 garlic cloves, smashed
½ tsp fennel seeds
6 TBSp olive oil, divided, plus more
Salt and pepper
4 sprigs basil
¼ loaf country-style bread, crust removed, torn into 2″ pieces (about 1 ½ c), divided
Preheat oven to 450°. Toss tomatoes, garlic, fennel seeds, and 3 Tbsp. oil in a large baking dish; season with salt and pepper. Roast, stirring occasionally, until the tomatoes are browned and the juices thicken, 30–35 minutes.
Transfer tomatoes to a large pot, add basil, 1 c bread and 4 c water. Bring to a boil and simmer about 8 – 10 minutes, stirring occasionally.
Toss the remaining bread with 3 TBSp olive oil, salt pepper and Italian seasoning. Bake until crips about 8 minutes.
Serve soup topped with bread. Drizzle with a little olive oil.