Step 1

Preheat oven to 400 degrees and line a baking sheet with foil or parchment paper.

Step 2

Combine tomatoes, balsamic vinegar, 2 tablespoons of the olive oil with salt & pepper in a large bowl and toss together.

Step 3

Spread the tomato mixture onto baking sheet.

Step 4

Cut off the top of the head of garlic, drizzle 1 tablespoon of oil on top and wrap tightly in tin foil. Place garlic on the baking sheet with the tomatoes and roast for about 45 minutes.

Step 5

While tomatoes and garlic are roasting, heat the remaining tablespoon of olive oil in a large heavy bottomed pot or Dutch oven over medium heat.

Step 6

Add the onions and garlic and sauté until softened, about 5-7 minutes.

Step 7

Once tomatoes and garlic are done roasting, add the tomatoes to the pot and squeeze the roasted garlic out of its paper into the pot as well. Continue to cook for another 5 minutes.

Step 8

Add parsley and basil, vegetable broth, tomato paste, brown sugar and cubed bread. Simmer for 20-25 minutes uncovered, stirring occasionally.

Step 9

Add the cream or milk and parmesan cheese and stir until combined and cheese has melted.

Step 10

Remove the soup from the heat and puree with an immersion blender or in batches in a regular blender until creamy.

Step 11

Season with salt & pepper to taste and serve with fresh basil.