Easy Tomato Soup with Pesto Grilled Cheese

by | Jan 27, 2021 | Recipes, Soups, Uncategorized | 5 comments

Late January can bring on the winter blues. As I write this, I find myself longing for a sultry summer breeze, my kids at day camp, a cold hefeweizen (with lemon), and time to chill with my wife. Fortunately, our taste buds can provide us with a virtual trip to a warmer spot on even the coldest winter day with a soothing recipe usually pulled out during these frozen weeks of mid-winter:  Tomato Soup with Grilled Cheese.

Adding to the warm weather feel, what screams summer more than tomatoes and basil? How about fresh mozzarella? Are you there yet? Is it possible to warm up with ingredients usually reserved for hot August nights?

I’m here to tell you that it is! I love to make tomato soup with a ton of basil accompanied by a grilled cheese with fresh mozzarella and pesto.

The tomato soup

Let’s start by making sure we have the correct ingredients in our pantry for our soup. First, we need excellent quality whole-peeled canned tomatoes. Before you frown about the word canned, please remember that quality canned tomatoes are harvested and canned at the height of their growing season. I recommend Jersey Fresh brand or anything from the San Marzano region of Italy. 

For this soup, I like running the tomatoes through a food mill (this one is the best) prior to adding to the soup. This will remove some of the seeds and unwanted fibers while giving the tomatoes a smooth consistency.

We will also need whole coriander and fennel seeds. These will be toasted and ground into a powder with a mortar and pestle. 

As far as fresh ingredients that are a little different from the norm, we will need a bulb of fennel. I love the sweet hint of anise flavor that fennel gives my tomato soup while working with the carrots to add body. 

As I mentioned, basil is an important addition to this soup. Here’s my method for infusing the soup with the basil without the hassle of fishing out leaves and stems: Tie a large bunch of basil together with one end of a length of kitchen string. Then tie the other end of the string to the pot handle. This allows the basil to steep in the simmering soup and be removed easily later.  This technique works well in sauce and soups when using any kind of stem herbs or leaves. I will include this description in the recipe method below. 

The grilled cheese

How to make tomato soup and grilled cheese

This is a fantastic grilled cheese sandwich that is a little different from the norm. I treat this sandwich like a pseudo-Monte Cristo. A Monte Cristo is a ham sandwich that is dipped in an egg and cream mixture before it’s pan-fried in butter. The reason I do that here is that we have two ingredients that this method really works well with, buffalo mozzarella and pesto. Dipping the sandwich in the custard creates a seal in the bread keeping the contents from seeping through.

I used Sesame Ezekiel Spouted Wheat Bread . I love Ezekiel this bread because it toasts extremely well (I have never eaten it non toasted!) and is a really healthy choice.

This simple tomato soup and grilled cheese recipe should do the trick to warm you up while transporting you to a tranquil summer night. Oh, the cold hefeweizen (with lemon) works well with this dish in the winter too!


Good ideas to please your palate and satisfy your soul

Hey there! I'm Geoff

I’m a lifelong cook and chef who has taken his career in some of the finest restaurants in California, Vermont, and New York City and woven my food and hospitality experiences into a successful career as a private chef for Ultra-high-net-worth families (UHNWIs) in the Greater New York City area.

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  3. Laura

    Tomato soup and grilled cheese was always a favorite when growing up but this recipe takes it to a whole new level. I love fennel and the addition to this soup was fantastic. I think the real scene-stealer here is the grilled cheese. I have never thought of making a grilled cheese Monte Cristo style and this really made it extra special with a very nice crunch. I used Dave’s Killer 21 Grain and Seed Bread since we did not have any Ezikiel in the house. The pesto and mozzarella on hearty grain bread with that custard dip before pan-frying made one of the best grilled cheese sandwiches I have ever had. Both my husband and son said it was one of their favorite grilled sandwiches and have asked when we will be having it again. Truly a comforting meal.


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