Few meals evoke the warmth and coziness of a bowl of tomato soup paired with gooey, perfectly crisp grilled cheese sandwiches. This recipe for roasted tomato soup with baked grilled cheese sandwiches offers an easy way to create a comforting, crowd-pleasing meal that’s perfect for any season.
Whether you’re feeding a family, entertaining guests, or simply craving a hearty dinner, this recipe ensures flavor and simplicity in every bite.
Why Roasted Tomato Soup Is the Ultimate Comfort Food

Roasting tomatoes before blending them into soup creates a rich, deep flavor that elevates the dish. This technique caramelizes the natural sugars in the tomatoes, enhancing their sweetness while adding a smoky complexity.
Even if fresh, in-season tomatoes aren’t available, this recipe works just as well with store-bought options, making it versatile and accessible year-round.
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This easy recipe transforms humble ingredients like garlic, onions, and broth into a silky, flavorful soup. The addition of cream, Parmesan, and fresh basil ties everything together for a perfectly balanced dish that tastes far more complex than it is to prepare.
Tips for the Best Grilled Cheese Pairing
The baked grilled cheese sandwiches are a game-changer. Baking them eliminates the need for flipping sandwiches on a stovetop, allowing for even cooking and less hassle.
The combination of cheddar and mozzarella ensures maximum meltiness, while buttered sandwich bread crisps to golden perfection in the oven.
Here’s why baking grilled cheese is a brilliant twist:
- You can easily scale the recipe up or down to serve any number of people.
- It’s hands-off, so you can focus on preparing the soup or entertaining guests.
- It guarantees perfectly crispy and gooey sandwiches without the risk of burning.
Pair these sandwiches with the roasted tomato soup for a timeless comfort meal everyone will love.
Substitutions & Modifications for Dietary Needs
This recipe is easily adaptable to suit various dietary preferences or restrictions:
- Vegan Option: Use plant-based butter, dairy-free cheeses, and coconut or cashew cream in the soup.
- Gluten-Free Option: Substitute gluten-free sandwich bread for the grilled cheese and ensure all other ingredients are gluten-free.
- Low-Carb Alternative: Replace bread with low-carb wraps or lettuce leaves to create a sandwich-inspired snack.
These simple tweaks make it easy to customize the recipe without compromising on flavor.
Pro Tips for Perfect Results Every Time
- Adjust Seasonings to Your Tomatoes: Out-of-season tomatoes may be more acidic, so taste the soup and adjust with a little sugar or cream to balance the flavors.
- Use High-Quality Cheese: Freshly grated Parmesan and good-quality cheddar make a noticeable difference in taste and texture.
- Make Ahead: The soup can be stored in the fridge for up to five days or frozen for up to three months, making it ideal for meal prep.
Why You’ll Love This Easy Recipe
This recipe takes the classic comfort of tomato soup and grilled cheese and makes it approachable for even the busiest cooks. By roasting the tomatoes and baking the sandwiches, you’ll get maximum flavor with minimal effort.
Grab your ingredients, preheat the oven, and enjoy the irresistible combination of roasted tomato soup and baked grilled-cheese sandwiches.
Easy Roasted Tomato Soup Recipe with Baked Grilled-Cheese Sandwiches
Ingredients
Roasted Tomato Soup:
- 3 pounds ripe tomatoes halved lengthwise
- 1 large yellow onion quartered
- 8 garlic cloves peeled
- 3 tablespoons extra-virgin olive oil
- 2 teaspoons fine sea salt plus more to taste
- ¼ teaspoon freshly ground black pepper plus more to taste
- 2 cups chicken bone broth or low-sodium chicken stock
- 4 tablespoons chopped fresh basil plus more for garnish
- ½ cup heavy cream plus more if needed
- ½ cup freshly grated Parmesan cheese plus more for garnish
- 2 tablespoons tomato paste
- 2 teaspoons sugar plus more to taste
Baked Grilled-Cheese Sandwiches:
- 3 tablespoons unsalted butter softened
- 8 slices sandwich bread
- 8 slices medium cheddar cheese
- 4 slices mozzarella cheese
Instructions
To Make the Roasted Tomato Soup:
- Preheat the oven: Set the oven to 400°F.
- Roast the vegetables: Arrange the tomatoes (cut side up), onion, and garlic on a baking sheet. Drizzle with olive oil, then sprinkle with ½ teaspoon of salt and the black pepper. Roast for 45 to 50 minutes, or until the edges of the vegetables are caramelized. Let them cool for 10 minutes.
- Blend the first batch: Add half of the roasted vegetables to a blender or food processor, along with 1 cup of chicken broth and 2 tablespoons of chopped basil. Blend until smooth, then transfer the mixture to a large pot.
- Blend the second batch: Blend the remaining roasted vegetables with the remaining 1 cup of broth and 2 more tablespoons of basil. Add this mixture to the pot.
- Simmer the soup: Heat the soup on medium. Stir in the heavy cream, Parmesan cheese, tomato paste, sugar, and the remaining 1½ teaspoons of salt. Adjust seasoning as needed, adding more cream, salt, or sugar to balance the flavor.
- Serve: Ladle the soup into bowls, garnish with fresh basil and Parmesan, and pair it with grilled-cheese sandwiches for dunking.
To Make the Baked Grilled-Cheese Sandwiches:
- Preheat the oven: If the oven is not already at 400°F, preheat it.
- Butter the bread: Spread softened butter on one side of 4 slices of bread. Place these slices, butter-side down, onto a baking sheet.
- Assemble the sandwiches: On top of each piece of bread, layer one slice of cheddar, one slice of mozzarella, and another slice of cheddar. Top with the remaining slices of bread, butter-side up.
- Bake the sandwiches: Bake the sandwiches for 10 minutes, flipping halfway through, until the bread is golden brown and the cheese is fully melted.
Notes
- Adjust the soup’s seasoning depending on the tomatoes’ natural acidity. Add more sugar or cream if the soup tastes too tangy.
- The grilled-cheese sandwiches can easily be scaled up or down to serve more or fewer people.
- Leftover soup can be stored in an airtight container for up to 5 days in the fridge or frozen for up to 3 months.
Nancy has been a plant person from an early age. That interest blossomed into a bachelor’s in biology from Elmira College and a master’s degree in horticulture and communications from the University of Kentucky. Nancy worked in plant taxonomy at the University of Florida and the L. H. Bailey Hortorium at Cornell University, and wrote and edited gardening books at Rodale Press in Emmaus, PA. Her interests are plant identification, gardening, hiking, and reading.