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5 from 3 votes

Fresh Roasted Tomato Soup w/ Grilled Cheese Sticks

Course Dinner, Soup
Cuisine American
Keyword basil, grilled cheese, roasted, tomatoes
Prep Time 20 minutes
Cook Time 1 hour
Servings 4 servings
Author Divas Can Cook



  • 5 medium-sized vine-ripe tomatoes
  • 1 pint cherry tomatoes
  • 1/2 white onion sliced
  • 4-5 cloves garlic
  • 4-5 fresh basil leaves plus more for garnishing
  • oregano sprig
  • 1 ½ cups chicken broth
  • 1 tablespoon granulated sugar can use more or less
  • smoked sea salt to taste
  • black pepper to taste
  • heavy cream


  • 8 slices sandwich bread I use potato bread
  • 1 cup shredded cheddar cheese I like to use a mixture of different cheeses
  • 1/4 cup mayonnaise
  • 1/4 teaspoon garlic powder can add more if desired
  • parsley


  • Preheat oven to 375 F.
  • Brush a foil-line baking sheet with olive oil and set aside.
  • Cut tomatoes in half and place cut side down on the prepared baking sheet.
  • Place onions and whole garlic cloves on the baking sheet.
  • Arrange everything in a single layer.
  • Roast for 35-45 minutes.
  • Remove from oven and let cool.
  • Remove the skins from the tomatoes (they should slip right off. You can leave the skin on the cherry tomatoes if you plan on blending it really well)
  • Peel cooled garlic and place into the blender, followed by the tomatoes, onions, basil and oregano.
  • Blend until smooth (or lightly chunky if you prefer.)
  • Transfer mixture to a large deep skillet or pot.
  • Stir in enough chicken broth just until your desired consistency is reached.
  • Bring to a simmer and simmer gently until hot.
  • You now have a GREAT base. Time to bring it to life!
  • Add in smoked salt and black pepper a little at a time until well seasoned being sure to taste after each addition. Salt & pepper really brings out the flavor!
  • Use white sugar to bring down the acidity and to lightly sweeten if needed.
  • Feel free to add in garlic powder, onion powder or dried oregano and parsley for more flavor.
  • Ladle soup into bowls & garnish with fresh basil and a splash of heavy cream.
  • To prepare the grilled cheese, heat griddle on medium heat.
  • Mix together mayonnaise, garlic and enough parsley for a pop of color.
  • Brush 4 slices of bread with the mayo mixture and place mayo side down on the griddle.
  • Spinkle on cheese.
  • Brush the top slices of bread with the mayo mixture and place on top of the cheese (mayo side up)
  • When the underside of the sandwiches are golden, flip over and allow the other side to turn golden.
  • (Press the sandwiches a little with a spatula to flatten.)
  • When both sides are golden, remove from griddle and cut into 3 sticks.
  • Serve alongside the tomato soup.
  • Enjoy!