Roasted Tomato Soup with Grilled Cheese

The first spoonful hit me on a drizzly Tuesday when I had nothing but sad tomatoes and stale bread. I tossed the tomatoes in the oven more out of desperation than inspiration, and the smell that filled my kitchen 20 minutes later made me forget I was improvising. When I dunked that first grilled cheese cube into the soup, I understood why some meals feel like a hug. It became my go-to whenever the world felt too loud or too cold.

I made this for my sister once after she had a terrible day at work. She sat at my counter, silent and exhausted, and watched me cut those little cheese cubes. When she took her first bite, she laughed for the first time all evening. She said it tasted like childhood without the cafeteria sadness. Now she texts me every fall asking if its soup season yet.

Ingredients

• Ripe tomatoes: The riper, the better. If theyre a little bruised or wrinkled, roasting saves them and brings out their natural sweetness.
• Onion and garlic: Roasting these with the tomatoes adds a mellow, caramelized depth you just cant get from sauteing alone.
• Olive oil: Dont skimp here. It helps everything brown and adds richness to the base.
• Dried thyme or basil: I lean toward thyme in winter and basil in summer, but either works beautifully.
• Vegetable broth: Homemade is lovely, but a good store-bought one does the job without fuss.
• Tomato paste: This little spoonful deepens the color and amps up that tomatoey punch.
• Sugar: Just a pinch if your tomatoes are tart. It balances without making things sweet.
• Heavy cream or milk: Optional, but it makes the soup feel like velvet on your tongue.
• Sharp cheddar cheese: The sharper the better for those croutons. It holds up to the heat and adds real flavor.
• Sandwich bread: White, wheat, sourdough. Whatever you have works as long as its soft enough to grill evenly.
• Unsalted butter: Softened butter spreads easier and gives you that perfect golden crust.

Instructions

Preheat and Prep:

Set your oven to 400°F and get your baking sheet ready. This is the moment to take a breath and enjoy the quiet before the kitchen smells incredible.

Arrange and Season:

Lay the tomato halves cut side up with the onion and garlic around them. Drizzle everything generously with olive oil, then season with salt, pepper, and your herb of choice.

Roast Until Caramelized:

Let them roast for 25 to 30 minutes until the edges are dark and the juices are bubbling. The tomatoes should look a little shriveled and smell like summer concentrate.

Simmer the Base:

Scrape everything into a pot, including those sticky pan juices. Add the broth, tomato paste, and sugar if needed, then let it simmer gently for 10 minutes to marry the flavors.

Blend Until Silky:

Use an immersion blender right in the pot, or work in batches with a countertop blender. Blend until completely smooth, then stir in cream or milk if you want it richer.

Build the Grilled Cheese:

Butter the outside of each bread slice, tuck cheese in the middle, and grill in a hot skillet until both sides are golden and the cheese melts into gooey perfection. Let them cool just enough to handle, then cut into little cubes.

Serve and Dunk:

Ladle the soup into bowls and pile those croutons on top. Watch them soften slightly as they soak up the soup.

Save

There was a night I served this to a friend who swore she didnt like tomato soup. She finished two bowls and asked for the recipe before she left. She told me later it was the croutons that won her over, but I think it was the whole experience, the warmth and the way comfort food can change your mind about things you thought you knew.

Making It Your Own

Ive added a pinch of smoked paprika when I want a campfire vibe, and once I stirred in a spoonful of pesto right before serving. You can swap the cheddar for mozzarella if you want it milder or Gruyere if youre feeling fancy. Some nights I skip the cream entirely and let the roasted tomatoes do all the work. The recipe bends to whatever your pantry or your mood suggests.

Storage and Reheating

The soup keeps beautifully in the fridge for up to four days and tastes even better the next day once the flavors settle. I dont recommend freezing it with the cream added, but the base freezes well for up to three months. Make the grilled cheese croutons fresh each time because they lose their magic once theyre soggy. Reheat the soup gently on the stove, stirring now and then, and add a splash of broth or water if it thickens too much.

Serving Suggestions

This soup feels complete on its own, but Ive served it alongside a crisp green salad with a lemony vinaigrette when I want to balance the richness. It also pairs beautifully with a crusty baguette for extra dunking or a handful of fresh herbs scattered on top for color and brightness.

• Top with a drizzle of good olive oil and a crack of black pepper for a restaurant touch.
• Serve in bread bowls if youre feeling festive or feeding kids who think edible dishes are magic.
• Pair with a light white wine or sparkling water with lemon for a simple, satisfying meal.

Save

This soup has become my answer to gray days and last-minute dinner guests. Its proof that simple ingredients and a little heat can turn into something that feels like home.

Recipe FAQ

→ Can I make this soup ahead of time?

Yes, the roasted tomato soup stores well in the refrigerator for up to 4 days or can be frozen for up to 3 months. Prepare the grilled cheese croutons fresh on serving day for maximum crispness, or store them in an airtight container for 2 days and reheat gently in the oven.

→ What type of tomatoes work best?

Ripe, in-season tomatoes deliver the best flavor. Roma or San Marzano varieties are excellent choices due to their higher flesh-to-seed ratio and natural sweetness. During off-season, quality canned tomatoes are a reliable alternative.

→ How do I make this dairy-free?

Substitute plant-based butter for regular butter, use dairy-free cheese for the croutons, and replace heavy cream with coconut milk, oat milk, or cashew cream. All components work beautifully with these alternatives while maintaining authentic flavor.

→ What cheese works best for the croutons?

Sharp cheddar provides bold flavor and excellent melting properties. Gruyère adds nutty depth, while mozzarella offers a milder, creamier option. Experiment with your preferred cheese to customize the flavor profile.

→ Can I use an immersion blender instead of a regular blender?

Absolutely. An immersion blender is actually ideal for this soup—blend directly in the pot for convenience and fewer dishes. For a traditional blender, work in batches and allow the soup to cool slightly before blending to prevent splattering.

→ How do I balance the acidity of the tomatoes?

A small amount of sugar naturally neutralizes tomato acidity without adding sweetness. Start with 1 teaspoon and adjust to taste. Alternatively, a splash of heavy cream or milk also balances acidity while enriching the soup.