Tomato Basil Soup + Grilled Cheese Bites Print Recipe Print Recipe

{Created/photographed by With Style and Grace}

Growing up, this is my hands down, favorite comfort meal, tomato soup and grilled cheese sandwich. Maybe it was all the bread and cheese I consumed that had me develope allergies to dairy and gluten? Whatever, it was totally worth it. Good news, this soup is DAIRY-FREE! If you have dairy allergies you know that most soups, especially those at a restaurant are made with dairy. Between the flavor from the roasted tomatoes and all the fresh basil, this soup is so incredible, next time, I’m doubling the batch!

I made this for my husband the other night and I kid you not, he has not stopped talking about it since. I asked my husband how he’d describe the soup and his response was, “The most amazing, awesome-ness tomato soup, ever!” I assure you he’s not five, that’s just the response you get when you hold his dinner – the soup – hostage. He’s been eating this soup {every night} with turkey meatballs and sprinkles of Parmesan cheese. I wonder what I can get with the major bonus points I just earned…

Looking for something different to serve for the Super Bowl? Fill little cups with the roasted tomato basil soup and using a large toothpick, skewer the bite-size squares of grilled cheese and lay on top of the cups.

This is also a great option for parties/entertaining and only want to serve light or bite-size appetizers.

NEXT: Healthy bite-size turkey meatballs!

Psst… Check it out, I added the option to print the recipe! Now that the not-so-techie self (me) figured it out, I’ll be going back and adding it to previous recipes.

Roasted-Tomato Basil Soup Recipe from Barefoot Contessa

Print this Recipe


  • 3 pounds ripe plum tomatoes, cut in half lengthwise
  • 1/4 cup + 2 Tbsp Olive Oil
  • 1 Tbsp kosher salt
  • 1 1/2 tsp ground black pepper
  • 2 cups chopped yellow onions (approx. 2 onions)
  • 6 garlic cloves, minced
  • 2 Tbsp butter – I left this out
  • 1/4 tsp crushed red pepper flakes
  • 28 oz. canned plum tomatoes with their juices – I used died tomatoes
  • 4 cups of fresh basil leaves, packed
  • 1 tsp thyme leaves
  • 1 quart (4 cups) chicken stock (or water)


Preheat oven to 400 degree F.

In a large bowl, toss the tomatoes, 1/4 cup of olive oil, salt +pepper.

Spread the tomatoes in a single layer on the baking sheet. Roast for 45 minutes.

In a large stockpot on medium heat, saute the onions and garlic with 2 Tbsp of olive oil, butter (optional), and red pepper flakes for 10 minutes or until the onions begin to brown. Add the canned tomatoes, basil, thyme, and chicken stock. Then add the oven roasted tomatoes and include any of the liquid on the baking sheet. Bring to a boil and then simmer (uncovered) for 40 minutes. If you have a food mill, use that to pass the soup through. I used a Cuisinart to puree – mine was more on the chunky side – but you could also use a blender.

Serve hot or cold. Enjoy!

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  • Nick

    Take one part comfort food, one part elegance, and you’ve got a masterpiece. Can’t wait to try these out!

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  • BBakeca Roma

    It looks great! I can’t wait to try it!

  • Kira

    Is there any chance you know how much this recipe will make? I want to make this for dinner for three people and I’m wondering if I shouldn’t double up on what you have here?


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  • Sook

    What a great idea! Love it.

  • Brandon

    Fancy grilled cheese and tomato soup? I like your style. This looks delicious, great entry.

    Twitter @theyummybits

  • Lily

    What Nick said! These do look like traditional comfort food but with such a lovely update. They look perfect for a fancy brunch.

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  • Cassandra

    This looks so good! I’m thinking of making it, is it gluten free also? I read the ingredience and it seems to be, just thought I would double check.

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  • Liesl

    Ooooh, yes please!  YUM! 🙂

  • Kevin (Closet Cooking)

    A perfect meal with an amazing presentation!

  • renagle

    I make this without the butter and add chopped red pepper and a stalk of chopped celery and a spash of Worcester sauce. You can eat it hot —or drink it cold from a glass. If you leave out the fat, the soup doesn’t separate. It is delicious! Homemade soup is the best as you can control the salt and make it as smooth or chunky as you like!

  • Angelina

    This is so freakin cute!