Tomato Soup with Pesto Grilled Cheese Dippers

In the interest of being honest, I should tell you that I had a tough time taking pictures of this.

TS2 copy

It’s not that this meal wasn’t photogenic or anything, so I’m not blaming its appearance. It’s just so good that I literally couldn’t pry my mouth away from my little pesto grilled cheese dippers…their edges smothered in creamy tomato soup.

If I could elect these sandwich strips for president, I would. Vice president? The soup. Duh.


Some of you are wondering why I’m posting two soups in such a short time span. After all, it seems like just yesterday I was squawking about Italian Wedding Soup! Cut me some slack – that was way back on Monday.

Truth be told – there are a couple reasons why we’re talkin’ soup…all over again.

  1. Baby, it’s cold outside.
  2. My mom has been bugging me for this recipe. Bad.

When I told my mom I was making tomato soup the other day, she started making audible gagging noises through the phone. I guess she’s not a fan?

I tried to convince her that MY tomato soup is actually really, really good, but I sort of just stopped when she protested. Wasn’t worth it, you know? But when mom and day came over the following day to go see some wedding venues with me and my hubby-to-be, Eric and I were enjoying some leftover soup for lunch.

Okay, that’s a little lie. My soup and sandwich were long gone. Eric enjoyed. I inhaled.


“Ooh, it smells good in here,” said mom. So as not to be rude, I offered her a bowl, which I eventually downgraded to a spoonful when she put up a fight. She still wouldn’t budge on her soup stance, but she did eventually wiggle her way over to the stove, where she could pretend she was standing for warmth. You and I both know what was really up though, right?!

She wanted that soup.


After all that huffin’ and puffin’, she finally tried a taste for herself. Then, she called me…twice…in an attempt to get this recipe for herself. I made her wait alongside the rest of you, but let’s get to this and get mom off my back 😉

First up, you’ve got to wash and prep some veggies. My favorite thing about this soup is the fact that it’s got a lot more than just tomatoes goin’ on. There are some onions in there because all good things start with onions; carrots, which cut the acidity of the tomatoes since they’re a little on the sweet side; and a couple celery stalks – leaves and all. All these vegetables add really great flavor this dish! Nutritionally speaking, their involvement in this recipe isn’t really awful either.

Broth Tomatoes

Once you’ve sauteed your trifecta of veggies until they’re soft and smell really good, add in a combo of fresh and canned tomatoes. It’s not tomato season, so I see no harm in using canned to supplement. If you can, go for no or low sodium so you can control that salt content!

Then, pour in a can of chicken or veggetable broth. I used chicken because it’s what I had on hand and I’m not a vegetarian, but for all intents and purposes, imagine I’m using veggie since that’s what I’ve instructed you to use in the recipe below. Classic “do as I say and not as I do” moment.


Add in some sugar and salt – then allow all your veggies to simmer in the stock and seasonings for a half hour or so. Go drink your morning coffee, check the mail, pay some bills – or just stare at your soup for thirty minutes. Shoot, I don’t care what you do! This time is essential to let the flavors develop – the long and short of it is that it makes for a better bowl of soup. So do it 🙂


After everything’s sat and simmered on the stove top, bust out your handy dandy immersion blender! Puree everything in that pot until you reach your desired consistency. In some soups, like broccoli cheddar, I like a little texture to it. For tomato though, I prefer a smoother soup. If you’re like me – just be patient and keep on pureeing!

Don’t have an immersion blender? You could definitely puree your soup in batches in the blender instead, but I’d recommend letting everything cool down a bit before doing so.



Before serving, we’re going to make a cream sauce to thicken the soup and make it all sorts of dreamy delicious. Start your cream sauce by melting a few tablespoons of butter in a small saute pan. Then, add an equal amount of flour. Use a whisk to work the flour into the butter until you have something that looks like what you see on the right. You’ll want to stir constantly as you cook for a minute or so. Then, add your milk on in to the mix.


ThickWhisk and whisk and whisk some more until everything comes together and thickens up nicely. It’ll take five minutes or so, but you’ll eventually get a really rich sauce that you can pour right into the soup pot. Hard to believe that’s only 1%, huh?!

Once you incorporate all of that creamy goodness into your tomato soup, simply stir in some pantry staple spices and simmer on low until you’re ready to serve.


You could, by all means ladle it up right now, but I’m suggesting you make yourself some pesto grilled cheese dippers to go alongside. They’re gonna be soooo good. Sigh.


GC4I’m guessing it’s safe to assume everyone reading has – at some point in their lives – made a grilled cheese? Good. Well, all you need to do to make pesto grilled cheese dippers is spread prepared pesto on one of your slices of sandwich bread before putting it in your pan. Once everything’s good and gooey – slap your sandwich on a cutting board, cut yourself some strips and voila!

You have the perfect vehicle to drive your tomato soup straight to your mouth.

Tomato Soup with Pesto Grilled Cheese Dippers

adapted from All Recipes
Serves: 4
Prep Time: 15 minutes
Cook Time: 60 minutes

For the Soup:
4 tomatoes, chopped
28 ounce can of diced tomatoes (low or no sodium is preferable)
1 cup finely chopped carrots
3/4 cup finely chopped onion
2 stalks of celery, finely chopped
1 (13.75 ounce) can veggie broth (or you can use chicken if that’s what you have on hand)
1 tablespoon white sugar
1 teaspoon salt
3 tablespoons butter
3 tablespoons all-purpose flour
1 cup 1% milk
2 teaspoons dried basil
1/2 teaspoon ground black pepper
1/4 teaspoon garlic powder

For the Grilled Cheese:
8 slices of hearty sandwich bread
8 slices of American – or other – melt-worthy cheese
prepared pesto
cooking spray or butter

Saute chopped onions, celery and carrots in a little olive oil over medium heat. Cook until everything’s soft and fragrant, 5-10 minutes. Add the tomatoes (fresh and canned) and broth – bring to a boil over medium-high heat in a stockpot, then reduce heat to medium-low. Add salt and sugar and simmer for 30 minutes.

After a half hour has passed, turn the heat off and use an immersion blender to puree the soup – the consistency is completely up to you. If you don’t have a hand blender, you can let everything cool a bit and then carefully transfer the soup in batches to puree in a traditional blender. Once your soup is at your desired consistency, keep it warm on the stove top while you make the cream sauce.

To make your cream sauce, melt the butter over medium-low heat in a small saucepan. Whisk in the flour, stirring until thick. Slowly whisk in the milk until smooth. Cook and stir, whisking constantly until thickened, about 5 minutes, then stir milk mixture in to the stockpot. Season with basil, black pepper, and garlic powder. Continue to simmer the soup on low to reduce and thicken while you whip up the pesto grilled cheese dippers.

To make your grilled cheese sandwiches, place one slice of bread in a pan with some butter or cooking spray over medium-low heat – and lay two pieces of thinly sliced cheese up on top. Spread a thin layer of prepared pesto on another slice of bread and press it firmly onto the cheese-covered slice that’s been cooking to complete your sandwich. Once it’s golden brown on the first side, flip your sandwich with a spatula so that the second side can follow suit. Then, transfer your grilled cheese to a plate or cutting board and cut into thin strips to serve with a big bowl of soup.


Dip. Eat. Repeat.


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2 thoughts on “Tomato Soup with Pesto Grilled Cheese Dippers

  1. cleaneatingveggiegirl February 2, 2013 at 5:02 pm Reply

    Both of these recipes look great, but I am totally digging the look and sound of those pesto grilled cheese dippers. So cute and so delicious looking!

    • Brie February 3, 2013 at 11:00 am Reply

      Thank you! They are completely crave-worthy. I might go into withdrawal this week since they’re not on my menu 😦

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