Roasted Tomato Soup with Grilled Cheese

Tomato soup and grilled cheese is the dinner I crave the moment the first leaves start falling. Roasting the tomatoes first changes everything: they turn sweet, a little smoky, and so much deeper in flavor than anything from a can.

Pair it with a golden, buttery grilled cheese for dipping and you have the ultimate cozy meal. Below you will find the full recipe, step-by-step photos, tips for the crispiest grilled cheese, and storage notes.

Why You Will Love This Recipe

• Real tomato flavor: roasting brings out natural sweetness.
• Silky and creamy: just a splash of cream, no heavy roux.
• Simple ingredients: tomatoes, onion, garlic, basil, and broth.
• The perfect pairing: crispy grilled cheese made for dipping.
• Freezer friendly: the soup base freezes beautifully.

Recipe at a Glance

• Prep time: 15 minutes
• Cook time: 50 minutes
• Total time: 1 hour 5 minutes
• Servings: 4
• Course: Dinner, Lunch, Soup
• Cuisine: American

Ingredients

For the Roasted Tomato Soup

• 3 pounds Roma tomatoes (about 12), halved
• 1 medium yellow onion, quartered
• 6 cloves garlic, peeled
• 3 tablespoons olive oil
• 1 teaspoon salt
• 1/2 teaspoon black pepper
• 2 cups vegetable or chicken broth
• 1/2 cup fresh basil leaves, plus more for serving
• 1/2 cup heavy cream
• 1 teaspoon sugar (optional, if tomatoes are tart)

For the Grilled Cheese

• 8 slices sourdough bread
• 3 tablespoons unsalted butter, softened
• 8 slices sharp cheddar cheese (or 2 cups shredded)

Ingredient Notes

• Tomatoes: Roma tomatoes are meaty with fewer seeds, which makes a thicker soup. Any ripe tomatoes will work.
• Garlic: whole cloves turn sweet and mellow in the oven, so do not be shy.
• Cream: for a dairy-free version, use full-fat coconut milk.
• Cheese: sharp cheddar gives the best flavor; add a slice of mozzarella or provolone for extra stretch.

How to Make Roasted Tomato Soup with Grilled Cheese

1. Roast the vegetables. Preheat the oven to 400°F. Arrange the tomatoes cut side up on a large rimmed baking sheet with the onion and garlic. Drizzle with olive oil and season with salt and pepper. Roast for 35 to 40 minutes, until soft and lightly charred.
2. Simmer. Transfer everything, including the juices, to a pot. Add the broth and basil, bring to a simmer, and cook for 10 minutes.
3. Blend. Blend with an immersion blender until smooth, or carefully blend in batches in a regular blender with the lid vented.
4. Finish. Stir in the cream over low heat. Taste and add the sugar if needed, plus more salt and pepper.
5. Build the sandwiches. Butter one side of each bread slice. Place 4 slices butter side down and top each with 2 slices of cheese and another slice of bread, butter side up.
6. Grill. Cook in a skillet over medium-low heat for 3 to 4 minutes per side, until deep golden and the cheese is melted.
7. Serve. Ladle the soup into bowls, top with fresh basil and a drizzle of cream, and serve with the grilled cheese cut into strips for dipping.

Tips for the Best Tomato Soup and Grilled Cheese

• Let the tomatoes char a little. Those dark edges add a smoky depth.
• Taste before adding sugar. Ripe summer tomatoes rarely need it.
• Low and slow grilled cheese: medium-low heat melts the cheese before the bread burns.
• Use mayo for extra crunch: spread a thin layer of mayonnaise instead of butter for a crispier crust.

Easy Variations

• Red pepper tomato soup: roast 2 red bell peppers with the tomatoes.
• Spicy: add 1/4 teaspoon red pepper flakes before roasting.
• Canned tomato shortcut: use two 28-ounce cans of whole peeled tomatoes, drained, and roast for 25 minutes.
• Grilled cheese upgrade: add a thin layer of pesto or a slice of tomato inside the sandwich.

Storage and Reheating

• Refrigerator: keep the soup in an airtight container for up to 5 days.
• Freezer: freeze the soup (before adding cream) for up to 3 months. Thaw, reheat, and stir in the cream.
• Grilled cheese: best eaten fresh. Reheat leftovers in a skillet or air fryer to keep them crisp.

Frequently Asked Questions

Do I have to peel the tomatoes?

No. Roasted tomato skins blend smoothly. For an extra-silky soup, pass it through a fine-mesh strainer.

Can I make it without cream?

Yes. It is still delicious; just add a little extra broth or a drizzle of olive oil for richness.

What is the best bread for grilled cheese?

Sourdough is sturdy and crisps nicely, but thick-cut white or Texas toast also works well.

Can I use cherry tomatoes?

Yes. Roast them whole for 25 to 30 minutes until they burst.

Final Thoughts

This Roasted Tomato Soup with Grilled Cheese is simple comfort food done right. Roast, blend, dip, and enjoy. If you make it, let us know in the comments how it turned out.