Roasted Tomato Basil Soup with Grilled Cheese

There’s something about tomato soup and grilled cheese that instantly brings me back to being a kid. It’s one of those classic comfort food combinations that never gets old. And even now, whenever I’m craving something cozy, easy to make, and a little fun, this roasted tomato basil soup with grilled cheese is exactly what I want.

My version starts with fresh cherry tomatoes, baby Roma tomatoes, sweet onion, and a whole head of garlic, all roasted until tender and packed with flavor. Everything gets blended into a silky tomato soup with fresh basil, chicken broth, and a little heavy cream.

And because tomato soup just isn’t the same without grilled cheese, I’m serving it with crispy sourdough stuffed with aged cheddar and Gruyère.

It’s nostalgic comfort food, just with a little something extra.

Why You’ll Love This Roasted Tomato Basil Soup

What makes this tomato basil soup so good is the roasting process.

Instead of simply simmering canned tomatoes in a pot, I roast fresh cherry tomatoes, baby Roma tomatoes, sweet onion, and garlic in the oven first.

Roasting helps concentrate the tomatoes’ natural sweetness and develops a deeper flavor.

The garlic becomes soft and mellow, the onions turn tender and sweet, and everything blends into a rich tomato base.

Then I strain the soup to give it a silky texture before simmering it with fresh basil and finishing with heavy cream.

The result is a creamy, comforting tomato basil soup that pairs perfectly with a golden, crispy grilled cheese sandwich.

Ingredients You’ll Need

For the Tomato Basil Soup

Fresh cherry tomatoes: I love using sweet cherry tomato varieties like SUNSET Flavor Bombs, Honey Bombs, or Sugar Bombs. Their natural sweetness works beautifully when roasted.

Baby Roma tomatoes: I combine the fresh cherry tomatoes with canned baby Roma tomatoes for a richer tomato flavor and a little extra body.

Sweet onion: Roasting the onion brings out its natural sweetness and helps balance the acidity of the tomatoes.

Garlic: I roast an entire head of garlic until the cloves become soft and mellow. Roasted garlic adds a beautiful depth of flavor without being harsh or overpowering.

Chicken broth: The broth helps create the right consistency and adds savory flavor to the soup.

Fresh basil: Fresh basil gives the soup its classic tomato basil flavor. I add it while the soup simmers so the flavor infuses the broth.

Heavy cream: A little heavy cream gives the finished soup a rich, velvety texture.

Red pepper flakes: I like adding a little heat to balance the sweetness of the roasted tomatoes.

Parmigiano Reggiano: Freshly grated Parmesan adds another layer of savory flavor.

Extra virgin olive oil: Olive oil helps roast the vegetables and adds richness.

For the Grilled Cheese

Sourdough bread: I love sourdough for grilled cheese because it gets beautifully crispy in the skillet while maintaining a little chew.

Aged cheddar: Aged cheddar brings a sharp, savory flavor that works perfectly with tomato soup.

Gruyère: Gruyère melts beautifully and adds a nutty, rich flavor.

Butter: Butter helps the bread develop that golden, crispy crust.

Why I Roast the Tomatoes First

Roasting is one of the most important steps in this recipe.

When you roast tomatoes at a high temperature, they begin to soften, release moisture, and develop a more concentrated flavor.

The sweet onion and garlic also transform in the oven.

The onion becomes softer and sweeter, while the garlic loses its sharp bite and turns mellow and almost buttery.

Once everything is blended together, you get a much deeper tomato flavor than you would from simply heating the ingredients in a pot.

It’s an extra step, but it’s absolutely worth it.

How to Make Roasted Tomato Basil Soup

1. Roast the Tomatoes, Onion, and Garlic

Start by preheating your oven to 425°F.

Slice the top off a whole head of garlic, drizzle it with olive oil, season with salt and pepper, and wrap it tightly in foil.

Add the fresh cherry tomatoes, canned baby Roma tomatoes, and quartered sweet onion to a lined baking sheet.

Season with extra virgin olive oil, salt, pepper, and red pepper flakes.

Place the wrapped garlic on the baking sheet and roast everything for approximately 45–60 minutes, until the tomatoes are tender and the garlic is soft.

2. Blend Until Smooth

Once the vegetables are roasted, transfer the tomatoes and onions to a blender along with their juices.

Squeeze the roasted garlic cloves out of their skins and add them to the blender.

Pour in one cup of chicken broth and blend until smooth.

3. Strain the Soup

For that silky, smooth texture, strain the blended tomato mixture through a fine-mesh strainer into a large pot.

This helps remove tomato skins, seeds, and any remaining coarse pieces.

It’s one of my favorite steps because it gives the soup a smoother, more refined consistency.

4. Simmer with Fresh Basil

Add the remaining cup of chicken broth and a large handful of fresh basil.

Bring the soup to a gentle simmer and cook for approximately 25–30 minutes.

This gives the flavors time to come together and allows the basil to infuse the broth.

5. Finish with Cream and Parmesan

Taste the soup and adjust the seasoning with salt and pepper.

Stir in freshly grated Parmigiano Reggiano to taste.

Then add the heavy cream and stir until fully incorporated.

The cream balances the acidity of the tomatoes and gives the soup that rich, velvety finish.

How to Make the Perfect Grilled Cheese

A good tomato soup deserves an equally good grilled cheese.

And for me, that means sourdough bread, aged cheddar, Gruyère, and plenty of butter.

1. Build the Sandwich

Start with two slices of sourdough bread.

Add two slices of aged cheddar and a generous handful of freshly grated Gruyère.

Close the sandwich and lightly butter the outside of both slices.

2. Cook Until Golden and Crispy

Heat a skillet over medium to medium-low heat with a little butter and olive oil.

Add the sandwich and cook for approximately 2–4 minutes per side, until the bread is golden brown and crispy.

The key is keeping the heat moderate so the cheese has enough time to melt before the bread gets too dark.

Once the cheese is melted and the sourdough is beautifully toasted, remove it from the skillet.

Slice it in half and serve immediately with the warm tomato basil soup.