Roasted Tomato Soup with Pesto Grilled Cheese is the upgrade your classic tomato soup and grilled cheese never knew it needed. Roma tomatoes, onion, carrots, red pepper, and two whole heads of garlic are roasted until deeply caramelized and sweet. Then blended into a silky soup and served alongside a delicious pesto sourdough grilled cheese.
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Why You'll Love This Recipe
Everything roasts on one sheet pan. Tomatoes, onion, carrots, red pepper, and two whole heads of garlic. The oven does 45 minutes of flavor-building!
That roasted garlic. Two whole heads squeezed into the soup after roasting. Sweet, jammy, and the reason this soup tastes nothing like the canned version. (Nothing against the can. But also yes, maybe something against the can haha)
Aioli on the outside of the grilled cheese instead of butter. It gets golden and slightly crispy. Game changer.
Pesto inside the grilled cheese. Sharp cheddar, mozzarella, and a generous layer of pesto on every bite.
Roasted Tomato Soup with Pesto Grilled Cheese Video
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Ingredient Notes
Roma Tomatoes: Roma tomatoes are the right call here because they are meatier and less watery than regular tomatoes which means they roast rather than steam and you end up with a deeper, more intensely tomato-flavored soup.
Two Whole Garlic Bulbs: By the time the garlic comes out of the oven it has transformed from sharp and pungent into something soft, sweet, caramelized, and almost nutty.
Balsamic Vinegar: Balsamic adds a subtle sweet acidity that deepens during roasting and adds complexity to the soup base, which makes people ask what the secret ingredient is. It is not overpowering, and you will not taste balsamic in the finished soup. You will just taste something richer.
Tomato Paste: Cooking the tomato paste in hot oil for a minute or two until it darkens and smells sweet and rich is the step that adds another layer of tomato depth on top of the already deeply caramelized roasted tomatoes. Two sources of concentrated tomato flavor in one soup. That is why this tastes so good!
Chicken Bone Broth: Chicken bone broth adds more body and a richer, more developed flavor than regular chicken broth or vegetable broth. The collagen in bone broth gives the finished soup a slightly silky texture even before the cream goes in.
The Aioli Grilled Cheese: This is not a standard grilled cheese. Each slice of sourdough gets aioli instead of butter, which browns and crisps in the pan in a completely different way. More flavor, more color, and a barely-there garlicky richness that pairs perfectly with the pesto and cheese inside. If you want a homemade pesto, try my Pistachio Pesto. It's INCREDIBLE!
Pro tip
The Secret to Perfect Soup
Blend the soup in stages if you do not have an immersion blender. Let the soup cool slightly before transferring to a standing blender and blend in batches with the lid slightly ajar to let steam escape. A sealed blender with hot liquid is a catastrophic situation. (Ask anyone who has made that mistake once.)
Substitutions & Variations
No roma tomatoes? Regular vine tomatoes or heirloom tomatoes work. The soup will be slightly thinner and less concentrated but still very good.
No heavy cream? Full-fat coconut milk works as a dairy-free substitute in the same quantity. The flavor will be very slightly different, but the texture will be equally silky. Cashew cream also works beautifully if you want to keep it vegan.
No aioli? Butter works as the classic substitute for the outside of the grilled cheese. But the aioli version is better. (Try it once and you will not go back.)
No pesto? A generous spread of sun dried tomato pesto or even just fresh basil leaves and a drizzle of olive oil inside the grilled cheese keeps the Mediterranean character of the sandwich. Store bought pesto works perfectly here. No need to make your own unless you want to.
Want to make it spicier? Double the red pepper flakes in the soup or add a teaspoon of Calabrian chili paste when you cook the tomato paste. The heat works beautifully against the sweetness of the roasted tomatoes and the richness of the cream.
FAQ
Yes and it is actually better the next day when the flavors have had time to develop further. Store in an airtight container in the refrigerator for up to 4 days. Reheat gently on the stovetop over medium low heat. Add a small splash of broth if it has thickened too much in the fridge. The grilled cheese is always best made fresh.
Yes. The soup freezes beautifully for up to 3 months. Freeze without the cream and add it fresh when you reheat. Cream-based soups can separate slightly after freezing but if you add the cream fresh after thawing and reheating the texture will be perfect.
Two likely causes. The vegetables were not roasted long enough to fully caramelize, or the tomato paste was not cooked in the oil long enough before the broth went in. Both steps are where the depth comes from. A flat soup usually means one of those two things was rushed. Taste and add more salt, a small splash of balsamic, and a pinch of red pepper flakes. That combination almost always fixes a flat tomato soup.
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⭐️ Recipe
Roasted Tomato Soup with Pesto Grilled Cheese
Ingredients
Roasted tomato soup
- 10 roma tomatoes halved
- 1 yellow onion roughly chopped
- 2 carrots cut into chunks
- 1 red pepper cut into chunks
- 2 small garlic bulbs tops cut off
- 2 tablespoon extra virgin olive oil
- 1 tablespoon balsamic vinegar
- 2 teaspoon garlic powder
- 2 teaspoon onion powder
- 1 teaspoon paprika
- 1 tablespoon dried oregano
- ½ teaspoon salt
- ½ teaspoon red pepper flakes
- ½ teaspoon black pepper
- 2 tablespoon tomato paste
- 3 cups chicken bone broth
- 6 fresh basil leaves roughly chopped
- ½ cup heavy cream
Pesto grilled cheese
- 8 slices sourdough bread
- ¼ cup aioli
- ½ cup pesto store bought or homemade
- 2 cups sharp cheddar shredded
- 1.5 cups mozzarella shredded
- 1 tablespoon extra virgin olive oil
Instructions
Roast the vegetables
- Preheat your oven to 400F. Place the halved roma tomatoes cut side up, roughly chopped onion, carrot chunks, and red pepper pieces on a large sheet pan. Drizzle with the olive oil and balsamic vinegar. Sprinkle the garlic powder, onion powder, paprika, dried oregano, salt, red pepper flakes, and black pepper evenly over everything and toss to coat.10 roma tomatoes, 1 yellow onion, 2 carrots, 1 red pepper, 2 tbsp extra virgin olive oil, 1 tbsp balsamic vinegar, 2 tsp garlic powder, 2 tsp onion powder, 1 tsp paprika, 1 tbsp dried oregano, ½ tsp salt, ½ tsp red pepper flakes, ½ tsp black pepper
- Cut the tops off both garlic bulbs to expose the cloves. Wrap them loosely in a piece of parchment paper and place cut side down on the sheet pan with the other vegetables.2 small garlic bulbs
- Roast at 400F for 45 to 50 minutes until the tomatoes are deeply caramelized and collapsing, the vegetables are tender and slightly charred at the edges, and the garlic is completely soft when pressed. Do not pull them early.
Build the soup
- Heat a drizzle of olive oil in a large pot over medium heat. Add the tomato paste and cook for 1 to 2 minutes stirring constantly until it darkens slightly and smells sweet and rich rather than raw and tinny.2 tbsp tomato paste
- Add all of the roasted vegetables and any juices that accumulated on the sheet pan. Add the chicken bone broth and the roughly chopped fresh basil. Stir to combine and bring to a gentle simmer. Unwrap the roasted garlic and squeeze every single clove out of both heads directly into the pot. Cook for 5 minutes so the flavors come together.3 cups chicken bone broth, 6 fresh basil leaves
- Use an immersion blender to blend the soup directly in the pot until completely smooth and silky with no visible chunks. If using a standing blender, let the soup cool slightly, blend in batches with the lid slightly ajar, and return to the pot. Season with salt and pepper to taste.
- Stir in the heavy cream and heat gently over medium low for 2 minutes until warmed through. Taste and adjust salt, pepper, and red pepper flakes as needed.½ cup heavy cream
Make the pesto grilled cheese
- Spread aioli on the outside of all 8 sourdough slices. This is the side that will go face down in the pan. Spread pesto generously on the inside of 4 slices. Top the pesto with the shredded sharp cheddar and mozzarella divided evenly between the four sandwiches. Place the remaining 4 slices on top aioli side out.
- Heat a drizzle of olive oil in a large skillet over medium low heat. Place the sandwiches in the pan and cook for 3 to 4 minutes without pressing them down until the bottom is deeply golden and the aioli has crisped slightly. Flip carefully and cook for another 3 to 4 minutes until the second side is equally golden and the cheese is fully melted all the way through.8 slices sourdough bread, ¼ cup aioli, ½ cup pesto, 2 cups sharp cheddar, 1 tbsp extra virgin olive oil, 1.5 cups mozzarella
- Remove from the pan and let it rest for 1 minute before cutting in half. The cheese needs that minute to set slightly so it does not all slide out the moment you cut it.
Serve
- Ladle the roasted tomato soup into bowls and serve with the pesto grilled cheese alongside for dipping.
Did you make this recipe? Let me know!