Garden Fresh Tomato Basil Soup, with Pesto Grilled Cheese Sandwiches – Caprese In A Whole New Way

Garden Fresh Tomato Basil Soup with Pesto Grilled Cheese

The skies are heavy with clouds. Heavy with great, heaving sobs of rain, which come and go, off and on, day and night. After each downpour the weight lifts temporarily, like a sigh of relief, before beginning again. My bare feet itch for the feel of the grass, the warm of the sun, the soft of the earth, while I wait for the storm to pass. Impatiently. These grey skies have turned me blue.

At last, the thirsty ground has drunk its fill. The world is breathing easier, now, and I venture out into my backyard — but this is not my backyard, anymore, it is a jungle. Mother nature has taken back my attempts at weeding, and everything is covered with tendrils of of green. And on the vine, I see, the first tomatoes beginning to blush, orange and red. Perhaps this stormy weather is not as bad as it seems. They are already candy sweet, and later, when I bring my hands to my face, I can still smell the sharp but pleasant aroma of their leaves.

To me, this is what summer smells like.

Cherry Tomatoes Fresh Basil

Of course, this is just the beginning. But the promise of sweet, vine-ripened tomatoes in combination with the recent abundance of basil I’ve been experiencing has had me craving a dish that could really embrace those summer flavors.

That was the inspiration for this soup. There is no cream or heavy ingredients, just bold, fresh tomato flavor. I paired the soup with a pesto grilled cheese sandwich, using the Basil and Sunflower Seed Pesto I made last week, and some fresh buffalo mozzarella. A classic caprese combination, put together in a whole new way.

Garden Fresh Tomato Basil Soup Garden Fresh Tomato Basil Soup with Pesto Grilled Cheese

This is the best tomato soup I’ve made. It is simple and flavorful, and incredibly easy to prepare. It is also naturally vegan and gluten-free, so feel free to omit the sandwich if you want to keep it that way. I finished the soup with a drizzle of olive oil, but a dollop of pesto would top it off nicely as well.

You can find my recipe for Basil and Sunflower Seed Pesto here, or use whatever pesto you like.

Garden Fresh Tomato Basil Soup
Makes about 6 servings

3-4 TBSP olive oil
3 lbs fresh tomatoes (I used about 8 vine-ripened tomatoes, but you could use heirloom, plum, or any other kind of tomato you like)
1 red bell pepper
3-4 cloves garlic, peeled and roughly chopped
1/2 yellow onion, diced
4 TBSP fresh basil, chopped
2 TBSP fresh oregano, chopped
1 TBSP balsamic vinegar
1 cup water, as needed
salt and pepper to taste
Pinch of sugar, optional (to round out the flavor if your tomatoes aren’t sweet enough)

1.   Preheat oven to 400f.
2.   Halve or quarter your tomatoes and lay the on a rimmed baking sheet, cut-side up. Halve or quarter the bell pepper, remove the seeds, and lay it on the baking sheet as well. Drizzle the tomatoes and pepper liberally with olive oil, and sprinkle with a pinch of salt.
3.   Place the tray in the oven and roast for 45-60 minutes, or until the tomatoes smell sweet and the edges have begun to shrivel up, rotating the pan halfway through.
3.   In a large pot over medium heat, saute the onion and garlic for 4-5 minutes. Add 1 TBSP of basil and all of the roasted tomatoes, bell pepper, and the juices that have collected in the baking sheet. Stir to combine, then blend smooth with an immersion blender (or, carefully transfer the mixture to a regular blender and place a dish towel over the top to avoid splattering. Pulse a few times, then blend until smooth and return to the pot).
4.   Add 1 more TBSP of basil, 1 TBSP of the oregano, and the balsamic vinegar. Stir to combine. Add water as needed to thin the soup to desired consistency.
5.   Season to taste with salt and pepper. Feel free to add a pinch of sugar, to taste, if the tomatoes aren’t sweet enough on their own. Stir in the remaining basil and oregano, and remove from heat. Serve immediately with a drizzle of olive oil, or store in the fridge overnight to let the flavors mingle. Leftovers can be stored in the fridge for up to a week, or frozen indefinitely.

Pesto Grilled Cheese Sandwiches
ingredients needed per sandwich
2 slices crusty bread (I used sourdough, but use what you like)
1-2 TBSP fresh basil pesto (recipe here)
a couple thin slices of fresh mozzarella cheese
a couple thin slices of sharp cheddar cheese (or another cheese you like)
a couple TBSP butter for the bread and the pan

1.   Heat a pan or griddle over medium-high heat. Butter one side of each slice of bread, and add a little butter to the pan.
2.   Place one slice of bread butter-side-down onto the skillet. Arrange the mozzarella and cheddar in an even layer on top of the bread.
3.   On the other slice of bread, spread a couple TBSP of pesto on the opposite side as the butter. Place this slice pesto-side-down onto the cheese. Cook for 2-4 minutes, or until the bottom piece of bread is golden and toasty. Adjust the heat if needed to keep the bread from turning too dark.
4.   Flip, and cook on the opposite side until it is also golden and toasty, and the cheese has become gooey and melty. Serve immediately.


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42 Responses to Garden Fresh Tomato Basil Soup, with Pesto Grilled Cheese Sandwiches – Caprese In A Whole New Way

  1. Jen @JuanitasCocina July 9, 2013 at 10:35 pm #

    I wish it weren’t so hot, because I would be gobbling this up like a champ!

    • Willow Arlen July 10, 2013 at 4:57 pm #

      Just wait till the end of the season – I’m planning to make a big batch of this soup before the tomatoes go away so I can enjoy it in the cooler months!

  2. mimi rippee July 10, 2013 at 12:25 pm #

    This looks so good. I’m making both of these!

  3. Anonymous July 10, 2013 at 12:54 pm #

    This looks fabulous – I’m a soup fan and eat it all times of the year – here in Tucson, if you wait until it is cold enough you wil NEVER have soup! I’ll be trying this, probably this weekend.

    • Willow Arlen July 10, 2013 at 4:58 pm #

      Me too, soup is a favorite! I hope you like this one!

  4. movita beaucoup July 10, 2013 at 1:14 pm #

    Should 2.0 and I be fortunate enough to have our last meal on earth together, I believe it would be tomato soup with grilled cheese sandwiches. When things are particularly busy or stressful, it’s our go-to comfort food. Also, it’s one of the only meals 2.0 confidently prepares (unassisted) for me. Your version looks amazing. I think 2.0 is ready for the next step…

  5. Nik Sharma July 10, 2013 at 4:12 pm #

    This looks very delicious and a perfect comfort food recipe! Love it!

  6. Nik Sharma July 10, 2013 at 4:13 pm #

    Also for some reason the first photograph does not load but the rest of the pictures do.

    • Willow Arlen July 10, 2013 at 4:59 pm #

      Thanks for pointing it out… I’ve done some fiddling around and it seems to be a glitch with the server that hosts my site… should be fixed now, but let me know if the problem persists on your end!

  7. Richa July 10, 2013 at 6:31 pm #

    this soup looks just perfect! i can imagine it tastes that way too

  8. Cassandra July 11, 2013 at 11:33 am #

    First up, I should make this soup to banish any shudder-worthy memories of canned tomato soup, which I hated. This recipe looks like summer in a bowl!

    Finding this recipe on Pinterest led me to your site, and now I want to bookmark everything for future kitchen adventures!! Please keep up the stellar photography, info, and recipes–I’ll definitely be back!

    • Willow Arlen July 11, 2013 at 2:18 pm #

      Thank you! And thank Pinterest, too. Glad to have you reading along!

      I’m with you, canned tomato soup is not very good… there is one brand here that does okay in a pinch, but still, there is no comparison to homemade!

  9. shannon weber July 11, 2013 at 11:58 am #

    mmmm, tomato basil soup is an ESSENTIAL thing around my kitchen during the fall and winter months; i don’t know why i never think of it in the summer, when tomatoes are fresh! sounds perfectly lovely, especially with the pesto grilled cheese. My head explodes a little just thinking about it. :)

    • Willow Arlen July 11, 2013 at 2:19 pm #

      I don’t usually make soups in the summer either, simply because it’s too hot, but I really couldn’t resist the fresh tomatoes. I plan to make a big batch of this when there are too many tomatoes to know what to do with, and freeze it so we can enjoy it in the cooler months!

  10. Heidi at Food Doodles July 12, 2013 at 9:44 pm #

    This looks like my perfect meal! Yum! Everything looks gorgeous :)

  11. Kelly Blackwell @ Heres My Take On It July 14, 2013 at 12:34 am #

    Oh this looks amazing! My tomato plants never came to fruit, but I have a fabulous basil plant. I will definitely be giving this recipe a shot. Thank you so much for sharing! I’m dropping by and following via Google + from The Harvest of Friends hop. Hope you can stop by too.

    • Willow Arlen July 14, 2013 at 1:38 am #

      Thanks for stopping by – I hope you like the recipe!

  12. Gretchen @ Two Healthy Kitchens September 8, 2013 at 3:14 am #

    Oh … I cannot wait to make this! Tomato basil soup is a family favorite at my house – and I LOVE the spin on the grilled cheese. Yummmmmm!!! Already pinned it to share with my readers – I just know they will love this as well!

  13. Anonymous October 5, 2013 at 11:01 pm #

    This is seriously the best tomato soup I’ve ever had!! I’ve been tasting it throughout the process and it’s fresh, light and delicious. I got a ton of organic heirlooms at the farmer’s market … large ones, cherry size and medium and in a variety of colors and made this insanely good soup today!! Just finished making the pesto too. We aren’t big on white flour over here so I may use it to season cauliflower mash or spaghetti squash but I bet it would be amazing on fresh pasta! I was skeptical of using sunflower seeds in place of pine nuts but it is honestly the best pesto we’ve ever had too!! My family is so excited for dinner tonight!!! Thanks so much for sharing, I need to find the rest of your recipes. Great photos too! Thanks :)

    • Willow Arlen October 6, 2013 at 1:15 am #

      Thank you so much — I’m so glad you liked the soup and pesto! This absolutely made my day, thank you for telling me. :)

  14. Anonymous October 28, 2013 at 7:51 am #

    I am so using Miyoko Schinner’s homemade vegan mozarella recipe to make the grilled cheese! Thanks

  15. Carli May 28, 2014 at 10:46 pm #

    I made this a few weeks ago! Absolutely delicious. Everyone in my family loved it.

    • Willow May 30, 2014 at 1:27 pm #

      Awesome, I’m so glad you liked it! :)

  16. Janet September 2, 2014 at 11:07 pm #

    Made this tonight for my last day of summer before school starts! Loved how light and fresh the soup was and I loved it paired with the crusty bread. The pesto grilled cheese was the perfect combo! Thanks!

    • Willow September 3, 2014 at 12:33 pm #

      I’m so glad you liked it! Thanks for stopping back to comment. This reminds me I need to make a big batch of this soup before all the tomatoes disappear.

  17. Sometimes Silverware March 15, 2015 at 8:09 pm #

    This looks amazing! Tomato soup has always been a favorite of mine!

  18. gizem922 March 17, 2015 at 3:51 pm #

    These pics are amazing. i will share them on my blog here:

  19. Brenda April 2, 2015 at 11:55 am #

    I made this today its really fresh and light just needed more seasoning, I have had a little with some light crusty bread mmmmmmmmmmmmmmm yummmmmmmy, going to leave it in the fridge to infuse then eat tomorrow evening with my husband, making some warm bread. In uk i am just starting to grow my tomatoes so i bought from my local supermarket vine tomatoes they did the job. Thank you for sharing x

    Cant wait for my husband to taste!

    • Willow Arlen April 6, 2015 at 12:00 pm #

      Thanks, Brenda, I’m so glad you liked it! :)

      • Brenda Capstick July 19, 2015 at 11:07 pm #

        making again today, love it x

  20. Brenda Capstick August 7, 2015 at 2:18 pm #

    this is so very nice and fresh , will make again and again x

  21. Michelle October 5, 2015 at 4:29 pm #

    Just made this soup, and WOW! It is DELICIOUS! I’m amazed at how rich and creamy this is–and there’s no heavy cream in it!! This is just pure goodness. I LOVE the creamy caprese flavor, too. The tomato-basil-balsamic combination can’t be beat. Thanks so much for sharing!

    • Willow Arlen October 5, 2015 at 6:24 pm #

      Thank you for the wonderful comment, Michelle! I’m so glad you like this soup, it’s one of our favorites!

  22. Eylah Millard August 18, 2016 at 8:35 pm #

    This tomato soup recipe is amazing, and I love the pairing of a pesto grilled cheese.
    I have a huge tomato garden, so I am always looking for new recipes to handle the surplus. I had a slight variation on the grilled cheese, ( I was out of mozzarella and cheddar) and used parmesan and feta cheese instead. I will definitely be using this recipe again!

    • Willow Arlen August 18, 2016 at 9:58 pm #

      Oh, I’m so glad you liked the recipe, Eylah! Sounds delicious with the parmesan and feta. I’ll have to give that a try next time!


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