Creamy Tomato Soup with Grilled Cheese Croutons

It’s been a long, long week. Some weeks just seem to drag on, don’t they? I tried to get as much sleep as possible to perk me up during the day, but I suppose that my body isn’t used to it and it has just made me feel sluggish instead. Then, the other day, I started feeling kind of run down and sick, which it just the worst, but often to be expected this time of the year with the temperature fluctuating all of the time and everything. I just want the weather to decide what season it is so I can have some continuity in my life! One day it’s beautiful, breezy, and 70 degrees, the next it’s humid, muggy, and 80+ degrees. I’m not liking it one bit! That’s why, the other day, when I was feeling down and it was one of the cooler days, I decided to make tomato soup.

I’ve made tomato soup before, but it just wasn’t quite what I wanted it to be. Sure, it was tasty and full of ripe tomato flavor, but it just didn’t have the consistency or flavors that I was looking for when I set out to make it. This tomato soup, however, hit all the right notes, as far as I’m concerned. It was wonderfully creamy; almost velvety. This texture was achieved by not only thoroughly pureeing the soup with my brand new immersion blender, but also by straining it through a mesh sieve. A little extra work really does go a long way when making something as classic as tomato soup! I especially loved the use of sage in addition to basil. It added a bright, unexpected flavor to the usual basil and tomato combination. Sage has a slightly peppery flavor, which plays well against the bold tomatoes and pairs nicely with the delicate basil. The cream cut through the acidity of the tomatoes a bit, too, so you can just keep on eating. I made little “croutons” out of grilled cheese sandwiches, which Kramer especially loved, and sprinkled a bit of basil and sage over the top of everything for a beautiful garnish. This soup tasted just like fresh tomatoes, which is really what I look for in a tomato soup. I hope you’ll make a big pot of it soon before all of the good tomatoes are gone!

Creamy Tomato Soup with Grilled Cheese Croutons
Your ingredients.

Creamy Tomato Soup with Grilled Cheese Croutons
Peel your garlic, place them in a tin foil “packet”, and drizzle with some olive oil before closing up.

Creamy Tomato Soup with Grilled Cheese Croutons
Do the same with the shallot or onion.

Creamy Tomato Soup with Grilled Cheese Croutons
Core your tomatoes and drizzle them with salt, pepper, and olive oil. Roast in the oven for 375 degrees F for 30-35 minutes, until the garlic is golden and the tops of the skins on the tomatoes are beginning to just be a bit charred.

Creamy Tomato Soup with Grilled Cheese Croutons
Chiffonade your herbs and set aside.

Creamy Tomato Soup with Grilled Cheese Croutons
Remove your baking sheet from the oven when ready.

Creamy Tomato Soup with Grilled Cheese Croutons
Add in the herbs and puree, then add in the cream and the pinch of sugar and the salt and pepper to taste.

Creamy Tomato Soup with Grilled Cheese Croutons
Strain the soup through a mesh sieve to remove any bits that didn’t get pureed. Return to a pot to reheat, if necessary.

Creamy Tomato Soup with Grilled Cheese Croutons
Slice your bread for the grilled cheese. I used a baguette, because the crustier the bread, the better, in my opinion.

Creamy Tomato Soup with Grilled Cheese Croutons
Toast the sandwiches on both side until golden.

Creamy Tomato Soup with Grilled Cheese Croutons
Cut the grilled cheese into cubes or serve whole, it’s really up to you. I liked the “croutons” added to the soup, personally.

Creamy Tomato Soup with Grilled Cheese Croutons
Top with the cubed grilled cheese and a bit of the herbs and enjoy!

Creamy Tomato Soup with Grilled Cheese Croutons
Cook time: 
Total time: 
Serves: 3
Tomato Soup
  • 8-9 large tomatoes, washed and cored
  • 6 cloves of garlic, peeled
  • 1 shallot, quartered (use ¼ an onion if you don't have a shallot)
  • 1 teaspoon kosher salt
  • 1 teaspoon ground black pepper
  • 1 tablespoon olive oil
  • 4 leaves basil, sliced thinly (chiffonade)
  • 4 leaves sage, sliced thinly (chiffonade)
  • ¼ cup heavy cream
  • ¼ teaspoon sugar
  • salt and pepper, to taste
Grilled Cheese Croutons
  • 6 slices crusty bread
  • 2 tablespoons butter, plus more for the pan
  • 9 slices cheese (I used Swiss)
Tomato Soup
  1. Preheat your oven to 375 degrees F. Line a baking sheet with foil and spray lightly with non-stick spray. Place your cored tomatoes on the sheet. Make two foil packets and place the garlic in one and the shallot or onion in the other. Sprinkle the tomatoes, garlic, and shallot with the salt and pepper, then drizzle lightly with the olive oil. Close up the packets and place on the sheet with the tomatoes. Roast for 30-35 minutes, until the garlic is golden and the tomatoes are slightly charred on the top parts of the skin.
  2. Place the tomatoes, shallot, and garlic in a food processor or a large bowl. Sprinkle with half of the basil and half of the sage. Either use your processor or immersion blender to puree everything. If you need to work in batches, that's fine, just have a pot ready to put the pureed soup in to keep it warm. Add in the cream and sugar last and taste for seasoning (I added a pinch of salt and pepper and a bit more basil and sage to suit my tastes). Warm in a pot over medium heat to re-heat, if necessary (I used an immersion blender and did not need to do this).
  3. Divide the soup into 3 bowls. Sprinkle with any remaining basil and sage and top with the grilled cheese croutons (recipe follows).
Grilled Cheese Croutons
  1. Butter both sides of each slice of bread. Over medium-high heat, heat a small amount of butter (about a teaspoon) in a pan and wipe it away with a paper towel when foaming, so that the surface is non-stick but there are no pools of standing butter. Toast 2 slices of bread on one side for a minute or two, then flip. Add 3 slices of cheese to one of the toasted sides, then place the other slice, toasted side down facing the cheese, to top. Use a spatula to press together.
  2. Toast until the other side of the bread is golden, then flip and toast the other side of the sandwich. Remove to another place and continue until you have 3 sandwiches. Serve whole or cut up into small squares and use as croutons for a garnish.


32 Responses

  1. Heather E says:

    This looks awesome. I am always looking for a good tomato soup recipe. What kind of tomatoes did you use?

    • Sydney says:

      Heather: Thanks! I used regular ol’ on the vine hot house tomatoes, nothing special, since it’s starting to get cooler and the more interesting tomatoes are starting to not be so tasty. It was still a great soup, even with the average tomato! :)

  2. rita says:

    Putting the grilled cheese IN the soup – What an awesome idea!

  3. a-man says:

    How long does it approximately take to prepare this yummy soup?

    • Sydney says:

      A-Man: From start (coring the tomatoes, prepping the shallot and garlic, etc.) to finish (garnishes and all), maybe an 1 hr. 15 minutes, at the absolute most, if you’re a slower cook. It took me 1 hour, and I cleaned up my workspace and whatnot while the tomatoes roasted.

  4. Wei-Wei says:

    Grilled cheese croutons – a revolutionary idea.

  5. Mom says:

    I think the grilled cheese croutons is something wonderful! You better make this for your brothers when they come to see you! Grilled cheese and Tomato soup their all time favorite!

  6. Tawny says:

    your soup and croutons look great!! i love all your step by step photos too

  7. Alicia says:

    Oh yum! Grilled Cheese and tomato soup is my #1 comfort food!

  8. V. says:

    Boo, I couldn’t find fresh sage…think I could use dried?

  9. Chef Bee says:

    This is awesome! Tomato soup and grilled cheese sandwich is my favorite meal and you just made it better. Love the idea of the crouton.

    Plan B

  10. Dana says:

    I made a tomato soup with grilled cheese croutons! They’re such crunchy cheesy goodness!

  11. Jen says:

    I somehow have to make this today because it’s a crappy rainy day and only a tomato soup/grilled cheese combo can make it all better. Mmmm.

  12. Heather E says:

    Great, thanks, Sydney! I’m totally making this for a guest tomorrow night.

  13. […] to the chef-iest of us! But I did muster up some cooking strength last night and went to town on this excellent recipe from The Crepes of Wrath. Tomato soup and grilled cheese is a winter comfort food classic of mine and I felt that it was the […]

  14. Wendi says:

    Oh my goodness! Made the soup and “croutons” for dinner tonight. Rave reviews from the household. Thank you for pictures, it helped me not panic when it was time to puree. Easy instructions for real people. Excellent flavor!

  15. […] The original from Crepes of Wrath: […]

  16. jojo says:

    I just found this recipe and can’t wait for fall weather! I am freezing fresh tomatoes from my garden this weekend and this may be the first recipe I try when pulling them out of the freezer in September. Thanks.

  17. john says:

    I have never. ever. been a fan of tomato soup. I have enjoyed many tomato based soups such as minstrone, but never. ever. tomato soup. My wife has always felt the same way.
    You have changed that. My wife and I made this for dinner. It is divine! Thank you! We skipped the straining step, but followed all other directions. We used home-made italian bread and emmenthaller swiss for the croutons. We served it with a local red wine and were transported!

  18. shixi says:

    That looks great, but how to make the soup such thick without using flour?

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