Step 1

Preheat oven to 425 degrees F.

Step 2

Cut off ¼ inch of the head of garlic from the top. Place garlic on top of aluminum foil and drizzle with about 1 tablespoon of olive oil, ½ teaspoon salt and ¼ teaspoon ground black pepper. Fold up the aluminum foil and seal by twisting the foil. Set aside.

Step 3

On a large sheet pan, drizzle roma tomatoes with olive oil, and salt and pepper to taste (about 1 ½ teaspoons salt, ½ teaspoon pepper). Arrange tomatoes flat side up, without overcrowding the pan. Tip: use 2 sheet pans if needed, as overcrowding will lead to steaming and not roasting.

Step 4

Place the prepared garlic head on the same sheet pan, along with the tomatoes. Roast for 35 minutes, flipping the tomatoes halfway through. Set aside. Tip: If the tomatoes start to burn (from the caramelization), flip them over with tongs.

Step 5

In a large Dutch oven or pot, heat about 2-3 tablespoons olive oil over medium-high heat. Add the diced onions and saute until softened, about 6 to 8 minutes. Add thyme and Italian seasoning and cook until fragrant, about 1 to 2 more minutes.

Step 6

Stir in chicken broth, the prepared roasted tomatoes, the canned diced tomatoes, and fresh basil leaves. Then, squeeze out the garlic cloves from the head and add it to the soup.

Step 7

Bring to a boil and then reduce heat to simmer. At this point, season with salt and pepper to taste. Simmer, uncovered, stirring occasionally for about 20-25 minutes, until somewhat reduced.

Step 8

Using an immersion blender, blend soup until smooth. Add a little bit of sugar to taste (about ½ or 1 teaspoon) to remove the acidity of the tomatoes. Season with more salt and pepper to taste.

Step 9

Stir in heavy cream to taste, and simmer for another 1 to 2 minutes. Adjust soup until desired consistency by adding more broth or heavy cream. Garnish as desired and serve warm. Enjoy!