Cozy and creamy, this roasted tomato soup is the kind of recipe you’ll want on repeat all season long. The secret? Roasting the veggies first for that rich, homemade flavor you just can’t beat.
Preheat oven to 400 F. Arrange tomatoes, onion, carrot, and garlic on a rimmed baking sheet. Drizzle with olive oil, season with salt and pepper, and roast 35–40 minutes, until softened and caramelized.
Squeeze roasted garlic into a large pot, then add all roasted vegetables and pan juices. Stir in broth, oregano, and sugar, and simmer 15 minutes.
Blend soup until smooth (use an immersion blender or carefully work in batches with a standard blender). Return to pot, stir in heavy cream, and warm gently - do not boil. Season to taste.
Meanwhile, butter bread slices, sandwich with cheese, and cook in a skillet over medium heat for 3–4 minutes per side until golden and melted. Let rest 1 minute, then cut into bite-sized cubes.
Ladle hot soup into bowls and top with grilled cheese croutons.
Notes
Roast for the best flavor – I have tested this soup both with and without roasting, and trust me, roasting makes all the difference. It brings out a sweetness and depth you just can’t get otherwise.
Blending safely – I love my immersion blender for this (no spills!). If you use a regular blender, vent the lid so steam doesn’t build up.
Don’t skip the sugar – Just a teaspoon balances the acidity of the tomatoes. It won’t make the soup taste sweet, but it rounds out the flavor beautifully.
Adjust the creaminess - I usually go with heavy cream, but half-and-half or coconut milk work too. Coconut milk gives a lovely hint of sweetness.
Finishing touch – A swirl of pesto, olive oil, cream, or sprinkle of fresh basil makes it feel extra special.