Tomato Soup with Grilled Cheese; Reimagined

Tomato and red pepper soup with grilled cheese recipe

I put this recipe together after thoroughly ruminating on my true love of tomato soup and grilled cheese with the goal of making a masterpiece of this comfort food staple. I hope you enjoy it!

Serves 4. Prep 20 minutes, Cook 1 hour

Tomato soup ingredients

  • San Marzano whole tomatoes 28 oz ( I like whole for best flavor, but can use chopped or crushed)
  • 2 fresh tomatoes on the vine
  • 2 tbsp minced shallot
  • 2 tbsp red pepper fine chop
  • 1 Carrot, shredded
  • 2 generous tbsp roasted red peppers
  • Fresh basil, tbsp plus more for garnish when serving, washed and chopped.
  • 1/3 cup Vegetable broth
  • 1/2 cup milk or cream
  • 1 head of Garlic
  • Olive oil (enough for sautéing and roasting garlic)
  • Salt and pepper, to taste
  • Granulated Sugar, to taste


Please refer to pictures in slideshow below!

  • Preheat oven to 400 degrees preparing to roast garlic. Place garlic on square of foil and drizzle with olive oil, wrap up tightly and put in oven carefully. Roast garlic about 40-50 minutes. When finished, remove and allow to cool.
  • While garlic is roasting, cut out top of fresh tomatoes and criss cross bottom part (see picture). Place a pot of water on stove on high heat. Prepare an ice bath (bowl filled with ice and water). Once pot on stove is boiling, add salt. Toss in prepared tomatoes for approximately 3-4 minutes or until you see tomato skin start to peel off. Then remove tomatoes with slotted spoon and place into ice bath. Once cooled, remove skin and chop.
  • Mince shallot or onion
  • Fine chop red pepper
  • Sauté shallot and red pepper over medium heat using generous drizzle of olive oil (can add a shake or two of red pepper flakes if you like spicy or not) stir for about 2-3 minutes
  • Add canned tomatoes and stir. Add roasted garlic, fresh tomatoes, roasted red peppers and basil. Shred carrot into soup. Cook on medium low for 15-30 minutes.
  • Use a submersive blender to puree everything together.
  • Add milk or cream
  • Add 1 tsp granulated sugar (taste now, can add more sugar based on your preference)
  • Can top with parm and/or fresh basil

Grilled Cheese Sandwich

Always pairs well with tomato soup! Although grilled cheese sandwiches seem easy to make, they can be a challenge (maybe its just me, who knows). I have found butter is necessary to make the best cheese sandwich and grilling is a must.


  • 2 slices of bread (sourdough or bread of choice)
  • garlic clove
  • 4-5 slices of cheese of choice (ideas: mozzarella, smoked provolone, colby-jack)
  • butter


  • Toast 2 slices of bread, lightly
  • Rub one side of each toasted slice with garlic clove, then slather that same side with butter
  • Heat nonstick pan on medium-medium high, depending on your stove
  • Place butter side down of one piece of bread and top with cheese slices
  • Put other piece of bread on top of cheese butter side up, check to make sure cooking well underneath and flip. It’s important to monitor closely to avoid burning.
  • Cook to your preferred level of toastiness while letting cheese melt and done!

  • Finished product of cup of soup with grilled cheese
  • Picture of garlic wrapped in foil prior to placing in oven for roasting
  • Picture of tomatoes on the vine prepared for boiling to remove skins
  • Picture of tomatoes in ice bath
  • Picture of minced shallots and chopped fresh red pepper

5 Comments Add yours

  1. CarolCooks2 says:

    Ahhhhh. tomato soup one of my all time favourites 🙂

  2. Tom Knackstedt says:


    1. Hello Dad!! Thanks for visiting me humble blog~~

  3. knacks374 says:

    Taking an old favorite to a new level!

    1. Yes indeed! Thank you for visiting my blaaag! 😊

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