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–+ servings
Creamy tomato soup with a swirl of cream, served with a grilled cheese sandwich on a wooden table.

Tomato Soup & Grilled Cheese

Nothing says comfort quite like a warm bowl of rich and creamy tomato soup. Our homemade heirloom tomato soup is bursting with the vibrant flavors of ripe heirloom tomatoes, fresh basil, and a hint of heat from jalapeños. Perfect for a cozy night in or as a starter for your favorite meal, this easy tomato soup recipe is sure to become a family favorite.
5 from 1 vote
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Course: Appetizer, Main Course
Cuisine: American
Keyword: grilled cheese, sandwich, tomato soup
Prep Time: 15 minutes
Cook Time: 1 hour 20 minutes
Total Time: 1 hour 35 minutes
Servings: 4
Calories: 752kcal
Author: Lola Jay

Ingredients

Tomato Soup

  • 8 heirloom tomatoes or 1.25 lbs
  • 2 baby red jalapenos or 1 green jalapeno seeds removed
  • 6 large basil leaves
  • 1 large yellow onion
  • 1 garlic bulb or 8 cloves
  • 2 tablespoon olive oil
  • 2 tablespoon paprika
  • 1 teaspoon onion powder
  • 1 tablespoon Italian Soffritto trader joes or italian seasoning
  • 1 teaspoon salt more based on your salt preference
  • 2 tablespoon butter
  • 28 oz can San Marzano crushed tomatoes
  • 2 tablespoon butter
  • ½ cup heavy cream

Pesto

  • 1 garlic clove
  • Pinch of salt ½ tsp
  • 1 tablespoon pine nuts
  • ½ cup basil
  • ¼ cup grated Parmigiano Reggiano
  • 2 tablespoon olive oil

Grilled Cheese

  • 2 slices of artisan or rustic bread
  • ½ cup smoked cheddar
  • ½ cup fontina cheese
  • ½ cup gruyere
  • 1 tablespoon butter
  • 2 tablespoon pesto

Instructions

Tomato Soup

  • Preheat your oven to 375F.
    Hand adjusting oven temperature dial to 160 degrees, focusing on precise cooking settings at home.
  • I'm using 8 heirloom tomatoes or about 1.25 lbs. You’ll want to pick the best in season tomatoes. I caught these right in time. Chop your tomatoes into quarters.
    Hand slicing fresh Roma tomatoes on a wooden cutting board, perfect for cooking or salads.
  • I'm using my cute little Jalapenos but you can substitute with 1 regular green jalapeno or none if you prefer no spice. Keep in mind that red jalapenos are spicier than the green ones. This is because the green ones are picked earlier in the ripening process. I’m removing the seeds to keep the spice level mild.
    Person slicing red peppers on a wooden cutting board with a knife nearby.
  • Roughly chop 1 large yellow onion. I set about ¼ cup aside for later on. Chop the top of your garlic bulb as we will be baking it whole. Place your garlic, tomatoes, peppers, onions (reserve ¼ cup for later )and basil. Top with your salt, smoked paprika, pepper, and olive oil and bake for 45 minutes to an hour.
    Sliced tomatoes, onions, garlic, and basil with olive oil on a baking sheet, ready for roasting.
  • Once your veggies are done, add your butter to a pan and saute your reserved onions on medium heat until aromatic. Add in your veggies, crushed tomatoes, sugar, chicken broth, Italian soffrito and simmer on medium low for 10 minutes.
    Red tomato sauce cooking in a pot, stirred with a wooden spoon, perfect for pasta dishes.
  • Combine using an emulsion blender or blender. Add in your heavy cream.
    Blending homemade tomato soup in a pot, using a hand blender for a smooth, fresh texture.

Pesto

  • I’m making just enough pesto for my one grilled cheese but feel free to double or triple this recipes. I’m using 1 clove of my grilled garlic and 1 tablespoon of roasted pine nuts, and a pinch of salt
    Crush your pine nuts until a paste is formed.
    Person crushing pine nuts in a wooden mortar with a pestle on a wooden surface.
  • Roughly chop your basil and add to the paste, followed by the cheese and olive oil. (see video)
    Wooden mortar with shredded cheese and herbs on a cutting board. Perfect for pesto or seasoning preparation.

Grilled Cheese

  • Grate your cheeses.
    Hand grating cheddar cheese in a kitchen, with a sink and plant visible in the background.
  • Top your slices of bread with your pesto and cheese.
    Preparing cheese and pesto sandwich on wooden board. Hands adding shredded cheese on bread with green pesto spread.
  • Add butter to a pan on medium heat, and add in your sandwich. Flip over once brown and serve!
    Grilled cheese sandwich in a pan, toasted to perfection with melted cheese. Ideal comfort food cooking scene.

Video

Nutrition

Calories: 752kcal | Carbohydrates: 38g | Protein: 24g | Fat: 60g | Saturated Fat: 27g | Polyunsaturated Fat: 5g | Monounsaturated Fat: 21g | Trans Fat: 0.5g | Cholesterol: 120mg | Sodium: 1537mg | Potassium: 1403mg | Fiber: 9g | Sugar: 18g | Vitamin A: 5861IU | Vitamin C: 63mg | Calcium: 599mg | Iron: 5mg