Sunday Night Dinner – Roasted Tomato and Pesto Grilled Cheese (348/365)

In 365Project2014, Andrew, Cooking, Sunday Dinner by Simmie1 Comment

Roasted Tomato and Pesto Grilled Cheese


And before you know it, Sunday night has rolled around again. Tonight we hosted Sunday Night Dinner and we decided to turn the classic grilled cheese and tomato soup combo around. Andrew has been on a real squash soup kick lately so he wanted to make it again. Since classic grilled cheese has orange cheese and tomato soup is red, we decided to flip it. With orange squash soup, we needed something red in our grilled cheese. A quick internet search led us to Joy the Baker and this roasted tomato, pesto, and brie grilled cheese.

I started by quickly roasting the tomatoes in the oven.Grape tomatoes are sliced in half, sprinkled with olive oil, salt, and pepper and spread out on a baking sheet. They roast for 20 minutes until they’re soft and sweet.  

Roasted Tomato and Pesto Grilled Cheese

While I was at it, I whipped up a quick batch of pesto. A little basil, some pine nuts, freshly grated parmesan cheese, olive oil, and salt and pepper go into a food processor and five minutes later you’re good to go.

Roasted Tomato and Pesto Grilled Cheese

I got really hearty, grainy bread at the bakery cut into thick slices. A little butter on the outside of the bread for grilling and then just top it as you like.

Roasted Tomato and Pesto Grilled Cheese

We each made our own grilled cheese to the proportions of our liking. I topped mine with a hearty spread of pesto and a heavy sprinkling of freshly grated parmesan on one side and piled the other side with slices of brie and a good forkful of roasted tomatoes.

Roasted Tomato and Pesto Grilled Cheese

It was a good as it looks. Andrew said he would gladly pay $14 to a hipster in a cafe for that sandwich which I think counts this meal as a big success. The saltiness of the parmesan and pesto work so well with the sweetness of the tomatoes and the creaminess of the brie. The grainy bread went so well with everything else and provided a delicious base to the sandwich.

As I’m typing this up, I’m realizing I want another sandwich. It was that good. Sometimes getting fancy is totally worth it.


  1. Pingback: Grilled Cheese Take II (349/365) - simmiecakes

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