Tomato Soup & Grilled Cheese Sandwich-An Elegant and Classic Combo
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When soup season peaks, I am ready to welcome it into my home like a long-awaited houseguest. I am nothing more than a cozy bowl of soup myself. Tomato soup and grilled cheese are perfect for this time of year. Welcoming soup season but also holding on to summer and using up all the sweet summer tomatoes. This is the only time I use the phrase “holding on to summer”, okay-when talking about the fresh produce that can segue into fall.
My roasted tomato soup and grilled cheese are the perfect duo for bidding farewell to summer (get the heck outta here, summer!) and subtly welcoming fall. It is but an introduction and preview to the wonderful ‘ber months ahead.
You caught me at the right time.
This recipe is elegant yet simple. It’s perfect for a rainy, gloomy day outside, but when you open the door and walk into your home, you’re greeted by the aroma of roasted vegetables, garlic, basil, and homemade soup just waiting to make your day a little better.
Put your troubles aside, grab a bowl, make that grilled cheese, and settle in.
What You Will Need For Tomato Soup & Grilled Cheese
- Sharp knife
- Sturdy cutting board
- Baking sheet pans
- Parchment paper
- Blender
- Dutch Oven
- Non-stick pan
- Measuring spoons & measuring cups
Why You’ll Love This Combo
- Roasting brings out the flavor. Roasting just about any vegetable brings out its natural sweetness and makes it so much more flavorful. Life hack for eating more vegetables!
- A whole head of garlic. It sounds like a lot, but roasting mellows the garlic and gives the soup an incredible, comforting flavor in every slurp.
- Elegant but easy. This is the kind of meal that feels special enough to serve to guests but is simple enough to make on a weeknight.
- The grilled cheese is the perfect match. Crispy, buttery, cheesy, and delicious all on its own—but dunked into this soup? I don’t even have the words.
- Even better the next day. The flavors have time to chill, mingle, and get to know each other. This soup reheats beautifully and somehow tastes even better the next day.
Let’s Make Roasted Tomato Soup
Preheat your oven to 425°F and line your baking sheet with parchment paper.
Start by rinsing your tomatoes and red bell pepper. Cut the tomatoes and onion into quarters. Cut the pepper in half and remove the seeds and membranes. I like to remove the seeds because they can add bitterness and slightly change the flavor of the soup.
Cut the head of garlic in half horizontally, exposing all of those beautiful little cloves.
Place the tomatoes, onion, pepper, and garlic on your baking sheet. Drizzle everything generously with extra-virgin olive oil and season with salt and pepper.
Roast everything for 30–35 minutes, or until the vegetables are tender and beautifully roasted.
Once everything has cooled enough to handle, remove the tomato skins. Squeeze the roasted garlic cloves out of their skins and add everything to a blender.
Add a generous handful of fresh basil and blend until completely smooth. If you have a smaller blender, you may need to work in batches.
Pour the blended soup into a Dutch Oven , add chicken broth and stir to combined. Season with additional salt and pepper. Add a pinch of red pepper flakes if you like a little heat. It adds a nice warmth to the soup.
Stir in ¼ cup heavy whipping cream for a rich, velvety texture. Let the soup simmer over medium-low heat, partially covered, for 10–15 minutes, allowing all those roasted flavors to come together.
At the very end, stir in 1 tablespoon of butter. It’s a small addition, but it gives the soup that extra silky, velvety finish.
Now let’s get to the good stuff…
The Crispy Grilled Cheese
Tomato soup without grilled cheese is like popcorn without extra butter. Nachos without jalapeños. Turkey without gravy. A good book without a bookmark. Technically, you don’t need any of them. But why would you do that to yourself?
You Will Need:
- Your favorite hearty bakery-style bread. I used sourdough.
- Sliced mozzerella
- Sliced white cheddar
- Butter
- Mayonnaise
I know, mayo…weird. But, trust me. Have I ever lead you astray?
While you’re assembling your sandwich, melt butter in a nonstick pan over medium heat.
Layer your mozzarella and white cheddar between two slices of bread. Spread a thin layer of mayonnaise on the outside of each piece of bread.
Place the sandwich in the skillet and cook until the bread is deeply golden brown and crispy and the cheese is completely melted. Flip carefully 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.
And now, ladies and gentlemen…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.
You’re welcome.
Roasted Tomato Soup & Grilled Cheese Sandwhich
Ingredients
Method
- Preheat oven: Preheat oven to 425°F. Line a baking sheet with parchment paper.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- Finish: Stir in 1 tablespoon butter just before serving for an extra velvety finish.
- Assemble: Layer mozzarella and white cheddar between two slices of bread.
- Add the secret ingredient: Spread a thin layer of mayonnaise over the outside of both slices of bread.
- 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.
- 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.
- 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.
