Go Back
Roasted tomato soup with crispy grilled cheese on a platter, perfect for a cozy fall meal.

Roasted Tomato Soup & Grilled Cheese Sandwhich

Sweet roasted tomatoes, garlic, peppers, and fresh basil come together in a smooth, velvety soup paired with a crispy, cheesy grilled cheese. An easy, cozy meal that’s perfect for welcoming soup season.
Print Recipe Pin Recipe
Course: Soup
Cuisine: American
Ingredients Method Notes

Ingredients
  

Roasted Tomato Soup
  • 4-5 ripe tomatoes
  • 1-2 red peppers removes seeds and membrane
  • 1 large yellow onion
  • 1 whole head of garlic cut in half horizontally
  • kosher salt & freshly ground black pepper to taste
  • olive oil
  • fresh basil generous handful
  • 1-2 cups chicken brother as needed, for desired consistency
  • red pepper flakes optional & to taste
  • 1 tbsp butter
Grilled Cheese Sandwich
  • 2 sourdough bread slices or any hearty bakery style bread you prefer
  • 1-2 sliced mozerella
  • 1-2 sliced white cheddar
  • 1-2 tbsp butter
  • mayonnaise

Method
 

Roasted Tomato Soup
  1. Preheat oven: Preheat oven to 425°F. Line a baking sheet with parchment paper.
  2. Prep the vegetables: Rinse the tomatoes and pepper. Cut the tomatoes and onion into quarters. Cut the pepper in half and remove the seeds and membranes. Cut the head of garlic in half horizontally.
  3. Season: Place the tomatoes, peppers, onion, and garlic on the prepared baking sheet. Drizzle generously with extra-virgin olive oil and season with salt and pepper.
  4. Roast the vegetables: Drizzle additional olive oil directly over the exposed garlic cloves and season with salt and pepper. Roast everything for 30–35 minutes, or until the vegetables are tender and nicely roasted.
  5. Blend: Once the vegetables are cool enough to handle, remove the tomato skins. Squeeze the roasted garlic cloves out of their skins. Add the roasted vegetables and garlic to a blender along with a generous handful of fresh basil. Blend until smooth. If using a smaller blender, work in batches.
  6. Simmer: Pour the blended vegetables into a Dutch oven. Add chicken broth and stir until you reach your desired soup consistency. Season with additional salt and pepper. Add red pepper flakes if you want a little extra heat.
  7. Make it creamy: Stir in ¼ cup heavy whipping cream. Simmer over medium-low heat, partially covered, for 10–15 minutes, allowing all the flavors to come together.
  8. Finish: Stir in 1 tablespoon butter just before serving for an extra velvety finish.
Grilled Cheese Sandwich
  1. Assemble: Layer mozzarella and white cheddar between two slices of bread.
  2. Add the secret ingredient: Spread a thin layer of mayonnaise over the outside of both slices of bread.
  3. Cook: Melt butter in a nonstick skillet over medium heat. Place the sandwich in the skillet and cook 3-4 minutes per side over medium heat or until the bread is deeply golden brown and crispy and the cheese is completely melted. If the bread is browning too quickly before the cheese melts, lower the heat to medium-low and give it a little more time. That will help you get that perfect crispy outside and gooey cheese inside.
  4. Flip: Carefully flip the sandwich and cook the other side until equally golden and crisp. You may need to add a little more butter to the skillet when you flip.
  5. The pull. Carefully pull the sandwich apart and admire that beautiful, melty, stretchy cheese for a bit before dunking it straight into your roasted tomato soup.

Notes

Mona's Tip: Wrap the garlic tightly in aluminum foil to help the cloves roast evenly without burning.
Mona's Tip: If you want a lot more heat in the soup, add cayenne pepper (to taste) instead of the red pepper flakes. Start with a little, you can always add as you go.