Roasted Garlic Tomato & Basil Soup with Caramelized Onion Grilled Cheese

Few things feel more like a warm hug in a bowl than a steaming pot of tomato soup paired with a perfectly golden, gooey grilled cheese. This version takes comfort food up a notch: sweet roasted garlic, fresh basil, and a splash of cream transform the soup into something rich and indulgent, while the grilled cheese features sharp cheddar and a surprising twist — caramelized onion cheddar. Trust me, once you try it, you’ll never go back.

Why You’ll Love This Recipe

• Comfort food with a twist – roasted garlic + caramelized onion cheddar elevate the classic.

• Easy & cozy – simple steps, pantry staples, and minimal fuss.

• Customizable – swap cheeses, adjust herbs, or add toppings.

• Family-approved – nostalgic and satisfying for all ages.

  Roasted Garlic Tomato & Basil Soup

  • 2 tbsp extra virgin olive oil (plus more for garnish)

  • 1 large white or yellow onion

  • 1 bulb of garlic

  • 2 cans (28 oz each) crushed tomatoes (preferably San Marzano with basil)

  • ⅓ cup fresh basil leaves

  • 2 cups vegetable broth (or chicken broth for extra richness)

  • 1 tsp sugar

  • ½ cup heavy cream

  • Salt, to taste

  • Black pepper, to taste

  • Garlic powder, to taste

  • Optional garnish: Parmesan or Pecorino Romano cheese (about ¼ cup)

  Caramelized Onion Grilled Cheese

  • 2 slices sourdough bread (or your favorite bread)

  • Butter, enough to spread generously on both sides

  • 3 slices sharp cheddar cheese

  • 2 slices caramelized onion cheddar cheese

  Instructions

  Roast the Garlic

  • Preheat oven to 350°F.

  • Slice the top off the bulb of garlic, peel away the loose outer layers, drizzle with olive oil, and sprinkle with salt.

  • Wrap tightly in foil and roast 40–60 minutes until golden and caramelized. Once cooled, squeeze the cloves out.

  Make the Soup

  • In a large pot or Dutch oven, heat 2 tbsp olive oil over medium heat. Add chopped onion and sauté until translucent.

  • Squeeze in roasted garlic, stirring to combine.

  • Add crushed tomatoes, fresh basil, broth, sugar, salt, pepper, and garlic powder. Stir and bring to a boil.

  • Lower to a simmer and cook for about 10 minutes.

  • Blend with an immersion blender (or in batches in a blender) until smooth.

  • Stir in heavy cream, adjust seasoning, and garnish with olive oil, fresh basil, and optional cheese.

  Make the Grilled Cheese

  • Preheat a frying pan with 1 tbsp butter.

  • Butter both sides of each bread slice.

  • Layer cheeses between bread slices and toast until golden and crispy on both sides, with cheese fully melted.

  • Slice diagonally and serve alongside hot soup.

• Serving Suggestions

  • Garnish soup with fresh basil leaves or a swirl of cream.

  • Pair with a crisp green salad for balance.

  • Add extras to grilled cheese: bacon, tomato slices, or caramelized onions for even more flavor.

  Storage & Reheating

  • Soup: Store in an airtight container up to 4 days in the fridge or freeze up to 3 months. Reheat gently on the stove.

  • Grilled Cheese: Best fresh, but re-crisp in a skillet or toaster oven.

    
    

  ✨ This is comfort food at its finest: cozy, rich, and absolutely irresistible. The roasted garlic adds depth, the basil keeps it fresh, and that caramelized onion cheddar grilled cheese? Pure bliss.

Want to see more? Follow me on instagram to participate in selecting which recipes get featured on the blog every week!