Step 1

Heat the oven to 400°F.

Step 2

Line a rimmed baking sheet with parchment paper. Spread the quartered tomatoes on the baking sheet, then sprinkle the garlic cloves throughout the tomatoes.

Step 3

Drizzle the tomatoes and garlic with the olive oil. Using your clean hands, rub the oil into the tomatoes and garlic cloves, leaving them evenly distributed throughout the baking sheet. Sprinkle with salt and pepper. Transfer the baking sheet to the oven and roast for 1 hour, or until the tomatoes are very soft and starting to caramelize around the edges.

Step 4

When the tomatoes have 30 minutes remaining, start the onions. Heat a dutch oven over medium heat. Add 1 tablespoon olive oil and heat until it shimmers. Add the onions and sautee until soft, stirring occasionally, 6-7 minutes. Sprinkle the onions with the dried basil and oregano and sautee until fragrant, 1-2 minutes.

Step 5

Add the balsamic vinegar to deglaze the pot; cook until the vinegar stops bubbling and reduces by half. Add the broth and fresh thyme to the pot, increase the heat to high and bring the liquid to a boil. Reduce the heat to medium low and simmer 10-15 minutes to infuse the broth with flavor. Turn off the burner.

Step 6

Remove the roasted garlic cloves from the baking sheet - use tongs, it will be hot! Set aside until cool enough to handle, about 5 minutes.

Step 7

Fish out the thyme bundle, and shake to release any leaves. Add the roasted tomatoes to the broth and onion mixture. Squeeze the roasted garlic from its paper shell and add to the soup mixture.

Step 8

Add the heavy cream if using and 1/4 cup fresh basil. Using an immersion blender, blend the soup in the pot until smooth. Add additional broth if needed to reach the desired consistency.

Step 9

Ladle the soup into bowls and garnish with additional fresh basil. Serve immediately. Store leftovers in a tightly sealed container in the fridge for up to 1 week, or in the freezer in an airtight container for up to 3 months.