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A garlic grilled cheese held over a bowl of roasted tomato soup topped with basil, cream and Parmesan.
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Roasted Tomato Soup with Garlic Grilled Cheese

Three pounds of heirloom tomatoes roasted with a red pepper, a whole onion and two bulbs of garlic until everything blisters, then blended smooth and finished with Parmesan, mozzarella and cream. Served with a sourdough grilled cheese built on garlic-basil mayo. Cozy, almost entirely hands-off, and it only gets better the next day.
Prep Time15 minutes
Cook Time50 minutes
Total Time1 hour 5 minutes
Course: dinner, lunch, Soup
Cuisine: American
Keyword: homemade tomato soup, roasted tomato soup, tomato soup and grilled cheese
Servings: 6 servings

Ingredients

For the Soup

  • 3 pound mixed heirloom tomatoes quartered
  • 1 red bell pepper cored and quartered
  • 1 yellow onion peeled and quartered
  • 2 bulb garlic peeled
  • 3 tablespoon extra virgin olive oil
  • 2 teaspoon salt for roasting
  • 1/4 cup Parmesan freshly grated
  • 1/4 cup mozzarella shredded
  • 1/4 cup heavy cream
  • 1 teaspoon salt for finishing
  • 2 teaspoon black pepper
  • 2 tablespoon fresh basil chopped
  • 1 tablespoon fresh thyme chopped
  • 1 tablespoon fresh rosemary chopped

For the Garlic Grilled Cheese

  • 2 slice sourdough bread
  • 3 tablespoon mayonnaise
  • 1 teaspoon Italian seasoning
  • 1 tablespoon fresh basil chopped
  • 2 clove garlic finely chopped
  • 2 slice sharp cheddar
  • 2 slice provolone
  • 2 tablespoon butter for the outside

Instructions

For the Soup

  • Heat the oven. Preheat to 400°F.
  • Prep everything. Quarter the tomatoes, core and quarter the red pepper, peel and quarter the onion, and peel the garlic cloves.
  • Season and roast. Spread everything on a sheet pan, toss with the olive oil and 2 teaspoons of salt, and roast for 40 to 45 minutes — until the tomato skins blister and split and the edges start to catch colour.
  • Let it cool a little. Give the pan 10 minutes or so. Hot liquid and a blender are a bad combination.
  • Blend smooth. Blend everything on the pan — juices included, that's where the flavour is — until completely smooth. An immersion blender or a standing blender both work.
  • Finish the soup. Pour into a pot over low heat and stir in the Parmesan, mozzarella, heavy cream, the remaining teaspoon of salt, the black pepper, and the chopped basil, thyme and rosemary. Stir until the cheese melts and it comes together.

For the Garlic Grilled Cheese

  • Make the garlic mayo. Mix the mayonnaise, Italian seasoning, chopped basil and chopped garlic together in a small bowl.
  • Build it. Spread the garlic mayo on the inside of both slices of sourdough, then layer the cheddar and provolone between them.
  • Butter the outside. Spread the butter across the outside of both slices — this is what gives you the crust.
  • Toast. Cook in a skillet over medium heat until deeply golden on both sides and the cheese has melted through. Cut on the diagonal and take it straight to the soup.

Notes

  • Use whatever tomatoes you have: I used a mix of red and orange heirlooms, but this works with whatever looks good. You want about 3 pounds total.
  • Two bulbs of garlic is not a typo: Roasting mellows it completely — it turns sweet and jammy rather than sharp. If you are nervous, start with one.
  • Do not skip the pan juices: Everything that collects on the sheet pan goes into the blender. That is the concentrated flavour.
  • Herbs go in at the end: Chopped and stirred into the finished soup, not roasted. They stay bright that way.
  • Mayo inside, butter outside: The mayo carries the garlic and basil into the sandwich; the butter is what browns the crust.
  • Storage: The soup keeps in an airtight container in the refrigerator for up to 4 days and freezes for up to 3 months. It is genuinely better on day two. Reheat gently on the stove.