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Tomato Soup with Grilled Cheese

  • Writer: rosabrinascucina
    rosabrinascucina
  • Nov 11, 2023
  • 3 min read

Updated: Dec 26, 2025

Tomato soup has become one of my all time favorites over the last few year. I used to totally be against it because I thought it was just the typical Sunday sauce being eaten with a spoon (not pairing sauce with pasta? the horror) until I finally made my own and realized how different and delicious it is. ESPECIALLY when its paired with grilled cheese!! One of the easiest soups I have ever made and can be cooked in an hour. It's one of those soups that can comfort you on any type of day <3


Ingredients:

Tomato Soup:

  • 10 tomatoes (I like to use a mix of different types, but fav is on the vine)

  • 1 yellow onion

  • 1 head of garlic (or 12-15 fresh cloves)

  • 2 tbsp extra virgin olive oil

  • 1/4 cup fresh basil

  • 1/4 cup dairy-free cream (can use regular as well)

  • 2 tbsp marsala wine

  • 4 cups chicken broth

  • 1 cup water

  • 1 tsp salt

  • 1/2 tsp cracked pepper

Grilled Cheese:

  • Sliced bread (favorite is sourdough obvi)

  • Gruyere Cheese (or whatever you like)

  • Parsley

  • Salt

  • Pepper

  • Garlic powder

  • Butter

Instructions:

  1. Preheat your oven to 400°F.

  2. Cut the tomatoes in half and place them on a baking sheet or deep dish pan.

  3. Slice the onion into wedges and add them to the baking sheet.

  4. If using head of garlic: remove the outer layer of skin from the head of garlic, leaving the cloves intact. Cut off the top of the head to expose the cloves and place it on the baking sheet.

    If using loose fresh garlic: just add to the pan

    If using minced garlic: 2 tbsp and add to pan

  5. Drizzle olive oil over the vegetables and sprinkle with salt and pepper.

  6. Roast for 40 minutes until the tomatoes are soft. Option to keep roasting until slightly charred. Remove from the oven and let cool 20 minutes.

  7. Once cooled, either in a blender or pot you can use an immersion blender with: Squeeze out the garlic, add the veggies, chicken broth, water, fresh basil, dairy free cream, marsala wine, salt, and pepper. Blend until smooth.

  8. Bring to a low boil over medium heat in a 6 quart pot. Simmer for 15-20 minutes, stirring occasionally. Taste and adjust salt, pepper, and garlic powder to your preference.

  9. While the soup is simmering, prepare the grilled cheese sandwiches. Heat a skillet over medium-low heat or keep the oven preheated to 400F.

  10. Spread butter on each side of the bread.

  11. Add the cheese, then the top piece of bread.

  12. Sprinkle parsley, salt, pepper, and garlic powder on the ouside of both pieces of bread.

  13. Place the grilled cheese on the pan or into the oven. Let it melt, making sure to flip and get each side crispy.

  14. Serve tomato soup warm with the grilled cheese sandwiches on the side for dipping.


A perfect meal for a cozy night in. Suggestion: If you love tomato soup, but also want some more protein, make some chicken cutlet to dip or enjoy on the side!


If you end up making this be sure to tag me and let me know how it was!


If you enjoyed this recipe, don't forget to follow us on Instagram @rosabrinascucina, TikTok @rosabrinas_cucina, or subscribe on Youtube @rosabrinascucina for more creations or explore our website for other comforting recipes to add to your collection.



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