Roasted Tomato Soup with Grilled Cheese Croutons
This Roasted Tomato Soup is proof that a cozy bowl of soup can bring big flavor! Roasting the tomatoes brings out their natural sweetness, while Calabrian chili adds a little heat. Top it with crispy, gooey grilled cheese croutons, and you’ve got everyone’s favorite comfort food pairing in every spoonful.
At a Glance
- Flavor: Rich roasted tomatoes, natural sweetness, and a little Calabrian chili heat, which can be omitted.
- Texture: Smooth and velvety, with crispy, gooey grilled cheese croutons.
- Method: Roast the tomatoes, blend, and finish on the stovetop.
- Perfect for: Cozy dinners, chilly days, and upgrading your tomato soup routine.
Why I love this recipe
I have a very simple rule: if we’re having soup for dinner, it better be worth getting excited about. And while I love a classic tomato soup and grilled cheese situation, I wanted this one to have a little more personality. Roasting the tomatoes gives them that deep, sweet flavor, and the Calabrian chili brings just enough heat to keep things interesting.
But let’s talk about those grilled cheese croutons, because I have absolutely no intention of being reasonable about them. They’re golden and crispy on the outside, melty in the middle, and ready to soak up all that tomato goodness. My advice? Make extra. A few will mysteriously disappear between the cutting board and the soup bowls, and I think we both know who will be responsible.
Ingredients
To make Roasted Tomato Soup, you will need:
- Tomatoes: I use a combination of Roma and cherry tomatoes for the best of both worlds! Roma tomatoes are meaty and relatively low in moisture, giving the soup body, while cherry tomatoes add little bursts of concentrated sweetness. You can absolutely use just one or the other, depending on what looks good at the store or needs rescuing on your counter. All Roma tomatoes may need a little help from the optional honey, while all cherry tomatoes will generally give you a sweeter soup. Either way, choose the ripest, most flavorful tomatoes you can find.
- Onion and garlic: Roasting the garlic mellows its sharpness and turns it soft, sweet, and almost buttery. Blended into the soup, it adds another layer of savory richness that makes this bowl so good! I use a yellow onion, but a sweet or white onion works too.
- Olive oil: Helps the vegetables roast and adds flavor. This is a good place for an olive oil you enjoy, but save your fancy finishing oil for a drizzle over the bowls!
- Tomato paste: A little boost of concentrated tomato flavor that gives the soup extra depth and richness.
- Calabrian chilies: These add a fruity heat that I absolutely love with the sweet roasted tomatoes. Adjust the amount to your heat tolerance, especially since brands can vary, or omit them entirely for a mild soup. A pinch of crushed red pepper flakes works as a substitute; start small and taste.
- Broth: Use chicken or vegetable broth, depending on your preference. A low-sodium broth gives you more control over the seasoning. You can also adjust the amount depending on how thick you like your soup.
- Heavy cream: Gives the soup a velvety texture and softens the acidity of the tomatoes. Half-and-half works for a lighter version, although the soup won’t be quite as rich.
- Butter: Adds richness to the soup and helps give the grilled cheese its golden, crisp exterior. Salted or unsalted works; just adjust the added salt accordingly.
- Fresh basil: Adds a fresh, fragrant note that’s so good with roasted tomatoes. Fresh is my preference here! If you only have dried basil, use a smaller amount and add it while the soup simmers.
- Honey (optional): Taste before adding! Ripe, in-season tomatoes may already be sweet enough, while out-of-season tomatoes can benefit from a little honey to balance their acidity. Add a little at a time – we’re making tomato soup, not dessert. A small amount of sugar works too.
- Salt and black pepper: Season to taste!
- Bread: I love a sturdy bread, like sourdough, for grilled cheese croutons that can hold their own in the soup. A good country loaf or thick-cut sandwich bread works too.
- Cheese: Choose a cheese that melts well for those gooey grilled cheese centers. Cheddar brings a sharper flavor (and I especially love a good aged Cheddar in mine), while Gruyère, Monterey Jack, or fontina are delicious options for mixing and matching. This is a very good opportunity to investigate your cheese drawer.
How to Make Roasted Tomato Soup
For me, a really good tomato soup starts with giving the tomatoes a chance to develop some flavor. Roasting brings out their sweetness and gives them those delicious browned edges, while the roasted garlic gives it an extra layer of wow-ness. Together, they make a soup that tastes like you put considerably more effort into dinner than you actually did. Always a win in my kitchen!
Then there’s the balance: a little Calabrian chili heat, fresh basil, and enough cream to make everything velvety without losing that lovely tomato flavor. I want a cozy, rich soup, but I still want the tomatoes to be the reason we’re all here.
And yes, I consider the grilled cheese croutons a very important part of this situation. You get crisp bread, melted cheese, and a little soup soaked into the edges, all in one bite. I recommend adding them right before eating so you get that glorious combination of crispy and gooey. Then keep a few extra within reach, because you’re going to want more.
Recommended tools and equipment: Rimmed baking sheet, parchment paper, large pot or Dutch oven, countertop blender or immersion blender, large skillet for the grilled cheese, cutting board, sharp knife, wooden spoon, spatula, measuring cups and spoons.
Here’s how I make this Roasted Tomato Soup recipe. As always, you will find the printable (and more complete) version of the recipe at the end of this post!
Step 1: Roast the Tomatoes, Onion, and Garlic
- Halve the Roma tomatoes and leave the cherry tomatoes whole. Cut the onion into halves or wedges, keeping the pieces large enough that they won’t burn before the tomatoes roast.
- Slice the top off the garlic head to expose the cloves.
- Spread the tomatoes and onion on a rimmed baking sheet, and nestle the garlic head onto the pan. Toss with olive oil, and season with salt and pepper. Give them room so they can roast and develop some color.
- Roast until the tomatoes are softened and browned in spots, the onion is tender, and the garlic cloves are soft. Those browned edges are flavor, so don’t pull the pan out too early!
Step 2: Cook the Tomato Paste and Calabrian Chilies
- Heat the butter in a large pot or Dutch oven over medium heat. Add the tomato paste and cook, stirring, until it darkens slightly in color.
- Stir in the Calabrian chilies and cook briefly to release their flavor. Start with less if you’re sensitive to heat – you can always add more later.
Step 3: Blend Until Smooth
- Transfer the roasted tomatoes, onion, and all the juices from the baking sheet to a blender. Let the garlic cool enough to handle, then squeeze the softened cloves out of their skins and add them.
- Add the cooked tomato paste and chilies, fresh basil, and enough broth to help everything blend. Blend until smooth, working in batches if necessary.
- When blending hot ingredients, follow your blender’s instructions: avoid overfilling, allow steam to escape as directed, and start on low speed. You can also combine everything in the pot and use an immersion blender, though a countertop blender usually gives a silkier result.
Step 4: Simmer and Add the Finishing Touches
- Pour the blended soup back into the pot and bring to a gentle simmer so the flavors can come together.
- Stir in the cream and warm gently. Add a little more broth if you prefer a thinner soup.
- Taste before adding the optional honey. Depending on the ripeness and sweetness of your tomatoes, you may need a little or none at all. Adjust the salt, pepper, and heat to your liking.
Step 5: Make the Grilled Cheese Croutons
- Butter the insides and outsides of the bread and sandwich the cheese between the slices.
- Cook in a skillet over medium-low heat until the bread is golden and crisp and the cheese has melted, flipping carefully. Keep the heat moderate so the bread doesn’t burn before the middle gets gooey.
- Transfer to a cutting board and let stand briefly before cutting into bite-size cubes. A serrated knife helps you cut through the crisp bread without squashing the sandwiches.
Step 6: Top and Serve
- Ladle the hot soup into bowls and add the grilled cheese croutons just before serving to preserve their crispness.
- Finish with fresh basil, a swirl of cream, or a drizzle of olive oil (I like using a basil olive oil), if desired. Serve extra croutons on the side for replenishing – and snacking.
Olivia’s Tips
- Roast for color, not just softness. For a flavorful roasted tomato soup, look for browned edges and some caramelization on the tomatoes and onions. If they’re soft but still pale, give them a little longer. Browning adds depth; blackened, burned bits can make the soup bitter.
- Save every drop of the roasting juices. Those juices belong in your soup! Pour them into the blender along with the vegetables. If there are browned bits stuck to the pan, loosen them with a splash of broth.
- Taste before adding honey. Roasting concentrates the tomatoes’ flavor, but their sweetness still depends on the variety, ripeness, and season. Add the optional honey only if the finished soup tastes too sharp. It balances the acidity without making the soup noticeably sweet.
- Use a countertop blender for the silkiest tomato soup. An immersion blender is convenient, but a countertop blender generally does a better job breaking down tomato skins and seeds. For an especially smooth finish, pass the blended soup through a fine-mesh sieve.
- Keep the heat gentle after adding cream. Warm the soup through without letting it boil vigorously, which can cause the cream to separate in the acidic tomato base.
- Cook the grilled cheese slowly enough to melt the center. Medium-low heat gives the cheese time to melt while the bread turns golden. If the bread browns before the cheese melts, lower the heat and briefly cover the skillet.
- Let the grilled cheese rest before cutting. Give the sandwiches 3–4 minutes on the cutting board before slicing them into croutons. This lets the melted cheese set slightly so it stays between the bread instead of spilling out. You want that cheesy goodness in your soup, not all over your cutting board!
- Keep the grilled cheese croutons separate until serving. They’ll soften as they sit in the soup, so add them to individual bowls at the last minute. If you’re expecting leftovers, store the soup and croutons separately. Future you deserves crispy croutons too!
Serving Suggestions
I serve this roasted tomato soup with a generous handful of grilled cheese croutons, added right before the bowls hit the table. A swirl of cream makes it look a little fancy, and a few torn basil leaves bring a lovely fresh finish. For extra flavor, try a drizzle of basil oil or chili oil – basil oil leans into the fresh, herby side, while chili oil is perfect for anyone who wants a little more heat.
You can also finish your bowl with freshly cracked black pepper, finely chopped chives, or a little freshly grated Parmesan. You don’t need all of these at once! Pick a couple and let those roasted tomatoes shine. If you’re serving guests, put the garnishes and extra croutons on the table so everyone can dress up their own bowl.
With the grilled cheese croutons, this is already a satisfying lunch or cozy dinner. I like a simple green salad with a bright vinaigrette alongside it to balance the richness. And if you’d rather serve a whole grilled cheese sandwich for dipping instead of cutting it into croutons, you will receive absolutely no objections from me.
Variations
I love this roasted tomato soup exactly as written, but there’s plenty of room to make it your own – or work with whatever is hanging out in your fridge!
- Make it gluten-free: Use gluten-free bread for the grilled cheese croutons and check that your broth and other packaged ingredients are labeled gluten-free.
- Try different herbs: Swap the basil for fresh thyme or oregano for a more earthy, savory flavor. Add these herbs while the soup simmers, starting with a small amount so they don’t overpower the tomatoes. Then remove the stems before serving.
- Make it dairy-free: Replace the butter with olive oil and use an unsweetened, unflavored plant-based cream in place of the heavy cream, or leave the cream out altogether. For the croutons, use dairy-free butter and your favorite melting vegan cheese.
- Make it vegan: Follow the dairy-free swaps, choose vegetable broth, and omit the optional honey or substitute a little sugar.
- Keep it mild: Leave out the Calabrian chilies for a tomato soup without the heat. This is also a good option when serving a crowd with different spice tolerances – you can put chili oil on the table instead!
- Add roasted red peppers: Blend in roasted red peppers for another layer of sweetness and a slightly smoky flavor if the peppers are charred. Start with one or two and adjust to taste.
- Switch up the grilled cheese: I use sharp cheddar and Gruyère, but other delicious combinations include fontina and Parmesan for buttery richness with a salty kick, Monterey Jack and smoked Gouda for a creamy, smoky filling, or Havarti and provolone for a mellow, extra-gooey grilled cheese. Use Parmesan as the supporting cheese so you still get plenty of melt! A thin layer of pesto inside the sandwiches is delicious too!
Storage and Freezing
Refrigerator: Let the roasted tomato soup cool, then transfer it to an airtight container and refrigerate for up to 3–4 days. Store any leftover grilled cheese croutons separately so they don’t soak up the soup and turn soggy.
Freezer: For the best texture, freeze the soup before adding the cream. Portion it into freezer-safe containers, leaving room for expansion, and freeze for up to 3 months. Thaw overnight in the refrigerator, then reheat and stir in the cream. Already added it? You can still freeze the soup, but it may separate slightly after thawing; whisk or briefly blend it to help bring it back together.
Reheating: Warm the soup in a saucepan over medium-low heat, stirring occasionally, until hot throughout. Avoid a vigorous boil, especially once the cream is added. If it has thickened, stir in a splash of broth or water.
Grilled cheese croutons: Refrigerate in an airtight container for up to 3–4 days. Reheat in an air fryer or oven at 350°F until hot and crisp, checking after a few minutes. For the best crispy-outside, gooey-inside situation, though, make them fresh while the soup reheats!
Frequently Asked Questions
No! The skins soften during roasting and get blended into the soup. A countertop blender does the best job of breaking them down. If you prefer an especially silky texture, strain the blended soup through a fine-mesh sieve.
Absolutely! Make the soup a day or two ahead and refrigerate until needed. Reheat gently, adjusting the consistency with a splash of broth if necessary. For the best texture, make the grilled cheese croutons just before serving.
Tomatoes vary in acidity and sweetness, especially depending on their ripeness and the season. First, check the seasoning – a little salt may help balance the flavor. Then add the optional honey a little at a time, tasting between additions. The cream also helps soften that sharpness.
Your tomatoes may have released more liquid, or you may have added more broth than needed. Simmer the soup uncovered, preferably before adding the cream, until it thickens to your liking. Next time, hold back some broth until after blending so you can adjust the consistency gradually.
Stir in a little broth or water until it reaches your preferred consistency. Add it gradually, then taste again and adjust the seasoning.
An immersion blender may leave small pieces of tomato skin or seeds behind. For a smoother result, use a countertop blender, working in batches and following the manufacturer’s instructions for hot liquids. You can also strain the soup through a fine-mesh sieve.
If you have extra roasted tomatoes or an unspiced batch of soup, blend some in to dilute the heat. A little additional cream can help mellow it, too. Avoid adding lots of broth alone, which can leave the soup thin without fully solving the problem.
Let the sandwiches rest for 3–4 minutes before cutting so the melted cheese can set slightly. Use a sharp serrated knife and gentle sawing motions instead of pressing down and squashing the bread. Add the croutons to the soup right before serving so they hold their shape and stay crisp longer.
More Cozy Soup Recipes
- French Onion Soup
- Easy Creamy Lasagna Soup
- Zuppa Toscana
- Creamy Chicken and Rice Soup
- French Lentil Soup
Roasted Tomato Soup with Grilled Cheese Croutons
Ingredients
For the roasted tomato soup:
- 2 pounds Roma tomatoes, halved lengthwise
- 1 pound sweet cherry tomatoes
- 1 large yellow onion, cut into wedges
- 1 whole head garlic
- 3 tablespoons olive oil
- Salt and freshly ground black pepper, to taste
- 2 tablespoons unsalted butter
- 2 tablespoons tomato paste
- 1 teaspoon chopped Calabrian chilies in oil, or to taste
- 2 cups low-sodium chicken or vegetable broth, plus more as needed
- 1 small handful fresh basil leaves
- ½ cup heavy cream
- 1 to 2 teaspoons honey, optional and only as needed
For the grilled cheese croutons:
- 4 slices sourdough bread
- 4 ounces sharp cheddar cheese, freshly grated
- 3 ounces Gruyère cheese, freshly grated
- 3 tablespoons softened butter, plus more if needed
Instructions
- Prepare the vegetables: Preheat the oven to 425°F. Arrange the Roma tomatoes, cherry tomatoes, and onion on a rimmed baking sheet. Slice the top off the garlic head to expose the cloves and place on the baking sheet. Drizzle olive oil over everything and season with salt and pepper.
- Roast: Roast for 30–45 minutes, until the tomatoes are softened and browned in spots and the onion is tender. Check the garlic; if the cloves aren’t soft, let it roast longer while you continue with the soup.
- Cook the tomato paste: Melt the butter in a large pot or Dutch oven over medium heat. Add the tomato paste and cook, stirring, for about 2–3 minutes, until it darkens slightly. Stir in the Calabrian chilies and cook briefly.
- Blend: Transfer the tomato paste mixture, roasted tomatoes, onion, and all the roasting juices to a blender. Once the garlic is cool enough to handle, squeeze the cloves out of their skins and add them along with the basil and broth. Pour in the broth, then blend until smooth, working in batches if needed and following your blender’s instructions for hot liquids.
- Finish the soup: Return the soup to the pot and bring to a gentle simmer. Stir in the cream and warm through. Add more broth if needed to reach your desired consistency. Taste and adjust the salt and pepper. Add honey a little at a time only if the soup needs sweetness to balance the acidity and spiciness.
- Make the grilled cheese: Lightly butter both sides of each bread slice. Divide the cheddar and Gruyère between two slices, then top with the remaining bread. Cook in a skillet over medium-low heat until golden and crisp on both sides and the cheese is melted, flipping carefully halfway through.
- Cut the croutons: Transfer the sandwiches to a cutting board and let rest for 3–4 minutes. Using a serrated knife, cut into ¾- to 1-inch cubes.
- Serve: Ladle the soup into bowls and top with the grilled cheese croutons just before serving. Finish with fresh basil, freshly cracked black pepper, and a drizzle of olive oil, basil oil, or chili oil – or a swirl of cream – if desired.
Notes
- Tomatoes: You can use all Roma or all cherry tomatoes, keeping the total weight at 3 pounds. Adjust the broth and optional honey to taste.
- Heat: Use less Calabrian chili for a milder soup, more for a spicy soup, or omit it.
- Honey: Ripe, in-season tomatoes may not need any. Taste the finished soup before adding.
- Croutons: Keep separate from the soup until serving to preserve their crispness.
- Storage: Refrigerate the soup and grilled cheese croutons in separate airtight containers for up to 3–4 days. Reheat the soup gently on the stovetop, adding a splash of broth if needed. Reheat croutons in a 350°F oven or air fryer until hot and crisp.
- Freezing: For best results, freeze the soup without the cream for up to 3 months, leaving room for expansion. Thaw overnight in the refrigerator, reheat gently, and stir in the cream. Soup frozen with cream may separate slightly; whisk or blend to bring it back together. Make the croutons fresh for serving.
