Homemade Tomato Soup with Pesto Grilled Cheese

There is something to be said for having comfort food to help get through the dreary and cold winter months. I’m not talking about Rocky Road ice cream or Oreos and a glass of milk, although that would probably work too. For me, what comes to mind is Campbell’s Tomato Soup and grilled cheese for dipping. Maybe it’s the rain or the lack of Vitamin D from Victoria’s cloudy climes, but I’ve been feeling particularly lazy and uninspired this past week and in desperate need of comfort food. I’m ashamed to admit that I had peanut butter and jam sandwiches for dinner three days last week and then bacon and eggs another time, which is very unlike me. So I’ve decided that something homey, healthy and relatively easy would be on the menu tonight to propel me through this next week on the right note.

Although tasty and inexpensive, Campbell’s soup was a little too easy tonight, so I tried to pull together something homemade that tasted close enough. I also love grilled cheese and have recently started putting a dab of pesto in the middle for some extra kick and have been experimenting with different cheeses to venture out of my Cheddar comfort zone. I didn’t have any regular pesto on hand, but at the back of the fridge was a jar of homemade pesto made from nettle plants that a friend from Saltspring Island had given me as a gift. For serving, call me crazy, but I get real enjoyment out of dipping my grilled cheese into the soup and then taking a bite of it when it’s warm and soggy. The perfect Sunday meal for eating while curled up on the couch in front of the TV.

Tomato Soup:

Makes enough for 4 – 5. Preparation and cook time: 30 minutes



2 tbsp olive oil

1 medium yellow onion, chopped

2 cloves of garlic, minced

2 large carrots, peeled and quartered (roughly 1 cup)

2 large cans of whole, peeled tomatoes in sauce (28 fl oz or 796 ml each can) – I used the yellow Italissima brand

2 cups of chicken stock

2 tbsp brown sugar

3 tbsp white vinegar

1 tsp salt

Sour cream, for garnish – Use about a tbsp on each soup bowl. Store bought sour cream can be fairly hard right out of the container, so you may want to whip a bit of it up beforehand in a small bowl with a whisk to give it a nice consistency for serving.

Sea salt, to taste



1. In a large soup pot, heat the oil on medium heat until hot. Add the chopped onions and stir for 2 minutes. Then add the garlic and stir both until the onions are translucent and soft. Add carrots and stir the mixture for 5 minutes more.

2. Add the canned tomatoes in sauce and with your hands in the pot break up the tomatoes in half. Add the remaining ingredients and continue heating on medium heat for 15 minutes. Remove from heat and let cool for 5 minutes.

3. Add the mixture to the food processor or blender and puree until of smooth, even consistency. Pour into bowl and serve with a sprinkling of sea salt and a dollop of sour cream, creme fraiche or plain yogourt.

Pesto Grilled Cheese

(Directions for 1 person)  Preparation and cook time: 10 minutes


2 slices of bread, any kind – though it looks nicer if you have old fashioned-style bread, sliced thick and on the diagonal

1 tbsp unsalted butter

1 tbsp vegetable oil

6 half inch thick slices of sharp cheddar (Brie or Camembert also work nicely)

Half a tomato, thinly sliced

1 tbsp pesto



1. In large frying pan on medium heat, heat the oil and melt the butter.

2. Place the the sliced cheese across one slice of bread to completely cover it. Spread the pesto onto the cheese, then cover with sliced tomatoes and add the top slice of bread.

Nettle plant pesto

3. Heat the sandwich in the oil for 3-5 minutes on each side or until golden brown and cheese is melted. Slice on the diagonal and serve with soup.


About gentlemangourmet

My name is Mike and even though I’m not always a gentleman, it’s safe to say I am in love with food. Like my more famous namesake, the kid on the cereal commercial from the early 80′s, I had an ability to eat just about anything and “like it.” I’ve become a tad more discerning since my toddler phase: I prefer Pinot Noir to the customary Shiraz my parents liked, I no longer eat parmesan cheese sprinkled from a container, and can pick out which ingredients I like or don’t in a recipe by smell alone. I blame my Lebanese heritage, my large Lebanese nose (all the better for smelling with) and exposure over the past few years to some exquisite ethnic cooking styles and cuisine, as well as to some stunning, inspiring cooks who are family or friends. I’ve included a lot of their favourite recipes on this site, as well as a few of my own that have become my staples over the years. I hope you find something here that you like. Happy cooking! View all posts by gentlemangourmet

One response to “Homemade Tomato Soup with Pesto Grilled Cheese

  • feastonthecheap

    Oh yeah, this is right up my alley… Grilled Cheese & Tomato Soup was my mom’s go-to meal when I was a kiddo…though I didn’t appreciate it at the time. Now, I could eat this all day every day. I love the pesto addition. Will have to try that the next time I make a batch.

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