I did something monumental this weekend.

Well, for me.

I actually planted something, like a vegetable, in a pot! At my house.

I had a bag of manure on my driveway and everything and I’d like to think that this is the start of a new me, buuuuut I complained the entire time. Not so surprising.

And yes, on this blog we declare tomatoes a vegetable. Seriously, don’t even start.

Ooooh so look at this bread.

So seedy right? Seedy in the good way, not seedy in the creeper way. It’s the harvest bread from Whole Foods and I could just chomp the entire loaf down in a few bites. It’s that fabulous.

…and look at this…

SO MANY VEGETABLES. Not the vegetables I planted, but so what?

Well, okay whatever. Maybe not. But lots of green and red stuff. Things that you can trick yourself into thinking are straight up veg. Basically I ate a salad on seeded bread.

Some of you may recall how over the last two years I’ve developed a snack fascination with toasted baguettes covered in tomatoes, basil, balsamic and fresh mozz to the point of golden bubbles. A very healthy addiction of sorts.

This is that, with another little bread hat. And roasted tomatoes…

These tomatoes get so sweet… and are almost reminiscent of a sauce right there on the sandwich. Sort of makes me want to like tomato sauce. Plus, we all know that roasting is the ONLY way I’ll eat anything that grows outdoors and is not of the fruit variety. With the melty cheese and the basil leaves… it was totally summer on a plate.

But the best part by far is the balsamic reduction, especially since I am a vinegar freak. I’ve been chewing on brine-y things since my crawling days, like olives and pickles and what not, so a sandwich like this appeals to both my sweet and sour side. And seriously, anytime something that looks like this can be considered healthy is pretty much the best day ever. Monday, you’re okay.

Roasted Tomato Caprese Grilled Cheese with Balsamic Glaze 

serves 2

6 tomatoes (vine or roma), sliced about 1/2 inch thick

1-2 tablespoons olive oil

1/2 teaspoon salt

1/2 teaspoon pepper

1/2 cup balsamic vinegar

3-4 ounces fresh mozzarella

12-15 basil leaves

4 slices seedy bread

Preheat oven to 325 degrees. Place tomatoes on a nonstick baking sheet and drizzle with olive oil, salt and pepper. Roast for 45-50 minutes. While tomatoes are roasting, add vinegar to a small saucepan and bring to a boil. Reduce to a very low simmer and cook for 10-15 minutes, until liquid reduces by about half and is slightly syrupy. Remove from heat, pour vinegar in a bowl or glass to pour, and let sit.

Once tomatoes are finished, heat a large griddle or skillet over medium heat. Brush the outsides of each slice of bread with olive oil, then place mozzarella on one slide, followed by tomatoes, basil (feel free to shred it if you’d like), more tomatoes and more mozzarella. Cook until cheese is melty and each side is golden, about 5 minutes per side. Serve immediately drizzle with balsamic.

FYI… this is my dinner tonight. Again.

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134 Responses to “Roasted Tomato Caprese Grilled Cheese.”

  1. #
    Lindsey — May 21, 2012 @ 5:04 pm

    Everything about this sounds amazing! I absolutely love roasted tomatoes and that balsamic reductions sounds like the perfect added touch!


  2. #
    Taylor — May 21, 2012 @ 5:40 pm

    You took my favorite combination to a whole new level…can’t wait to try it!


  3. #
    Rocky Mountain Woman — May 21, 2012 @ 6:23 pm

    Hey, that just became my dinner tonight! Go figure….


  4. #
    Lauren — May 21, 2012 @ 6:37 pm

    This looks so good I can’t even stand it. Seriously.


  5. #
    Maura @ My Healthy 'Ohana — May 21, 2012 @ 6:59 pm

    Mmm…I am loving everything caprese right now and I had totally forgotten about balsamic glaze, will have to make some right now! :)


  6. #
    CulinarilyCourtney — May 21, 2012 @ 7:16 pm

    I haven’t been able to eat tomatoes for about 3 months now because of stomach issues, but man, this recipe is screaming my name!!!!!


  7. #
    Jen @ keepitsimplefoods — May 21, 2012 @ 8:22 pm



  8. #
    Cookie and Kate — May 21, 2012 @ 8:57 pm

    My computer is being fussy today, which means that your first photo downloaded very slowly onto my screen. Rooooaaasstteeedddd tomatttoooo… drool. I want this sandwich tout suite!


  9. #
    Amanda N — May 21, 2012 @ 9:21 pm

    That looks amazing!


  10. #
    Adrienne — May 21, 2012 @ 10:13 pm

    Yes YES YES! I am OBSESSED with everything Caprese! And I love that bread from WF too!


  11. #
    Ashley's Cooking Adventures — May 21, 2012 @ 11:18 pm

    Such a great idea to roast the tomatoes AND to make a balsamic glaze. I want this in my life immediately!


  12. #
    Baking Serendipity — May 21, 2012 @ 11:31 pm

    Good grief. You’ve taken my favorite grilled cheese and done amazing things to it! I see a whole lot of roasted tomatoes in my summer ahead…thank you!


  13. #
    Harpa — May 22, 2012 @ 4:15 am

    This looks absolutely mouthwatering! And since I´m the spontaneous type I bought all the ingredients yesterday and everything was headed towards a yummy dinner… except… I roasted the tomatoes (never done that before) for 40 minutes without checking on them and when my oven ding-ding-dinged they where just completely black round thingies :( So I had a banana sandwich.
    But I´m giving it another go tonight!


    • Harpa — May 22nd, 2012 @ 4:43 am

      sorry, “…they were…”


  14. #
    Jennifer — May 22, 2012 @ 7:16 am

    Wow! A wonderful kicked-up grilled cheese. Looks amazing!


  15. #
    Dan — May 22, 2012 @ 7:43 am

    That looks amazing. I would put that on any restaurant menu I write. And may. Thanks for sharing!


  16. #
    Nina — May 22, 2012 @ 8:00 am

    Yummy! I just drooled all over my macbook!


  17. #
    idiosyncratic eye — May 22, 2012 @ 8:30 am

    I was chewing on farmhouse pickle onions even before I had teeth. Glad I’m not the only one. ;)


  18. #
    Anne Jasinski — May 22, 2012 @ 9:02 am

    Weird – I just discovered yesterday that you can buy terrific balsamic glaze in a bottle at the grocery store – which would make this recipe even easier. I’ve been squirting it on everything I can get my hands on. (Although I wouldn’t recommend on Frosted Shredded Wheat. Bad idea).


  19. #
    Anitra — May 22, 2012 @ 9:36 am

    have we figured out what wine goes best with this? Nevermind I’ll keep maiking then and eating them until I find one. Cheers :)


  20. #
    caroleena — May 22, 2012 @ 9:37 am



  21. #
    Mercedes@Satisfy My Sweet Tooth — May 22, 2012 @ 10:11 am

    Wow does this sandwich look amazingly decadent and delicious! I love the balsamic reduction drizzle to add that little hint of sweetness!


  22. #
    Moni Meals — May 22, 2012 @ 11:33 am

    oh wow~ I want to make this and what a top touch with that dressing. :)


  23. #
    Andrea — May 22, 2012 @ 12:06 pm

    YUM. I just brought home the “seeduction” loaf from whole foods this week and have been smearing avocado all over its toasted, nutty self like there’s no tomorrow.


  24. #
    Epicurious Brit — May 22, 2012 @ 12:33 pm

    I want to eat this, right now!


  25. #
    Jen Marie — May 22, 2012 @ 1:19 pm

    My mouth is literally watering right now. Caprese salad is one of my favorite things. This sandwhich is probably like a flavor explosion. I can taste it and smell it right now!


  26. #
    Jamie @ green beans & grapefruit — May 22, 2012 @ 1:40 pm

    mmmm sounds good.


  27. #
    Jenny D. — May 22, 2012 @ 4:04 pm

    Seriously, girl – I just made this for my husband & I for lunch and both of us, after just one bite, were near cussing about how incredibly amazing it was. Soooo freaking good!!!


  28. #
    Melissa — May 22, 2012 @ 7:38 pm

    I’ve been cyber-stalking (okay okay- reading) your blog for awhile now & I have to tell you how much I enjoy your take on everything! And how beautiful & artsy your pictures are! And how I giggle pretty much every single time because you say something that reminds me of me or one of my equally quirky friends. And I just have to tell you “THANKS!” and please don’t ever stop! :) That’s it.


  29. #
    Tracy {Pale Yellow} — May 22, 2012 @ 8:24 pm

    Those roasted tomatoes look amazing! I’ve never roasted before, I can’t wait to try!


  30. #
    brandi — May 23, 2012 @ 1:20 pm

    roasted tomatoes are the BEST. it’s like summer candy. yum.


  31. #
    Breanne — May 24, 2012 @ 1:39 pm

    I have fresh mozzarella in my fridge, ripe tomatoes on my counter and seed bread….this is dinner. Love the variation on caprese, yum!!


  32. #
    claudinne — May 24, 2012 @ 2:44 pm

    Imagine adding some avocado to this. OMG


  33. #
    Mary-Where's the Zoom — May 24, 2012 @ 6:51 pm

    I support grilled cheese in any form. This looks yummy. Great pictures, as always!


  34. #
    Shanna — May 24, 2012 @ 9:58 pm

    I made these last night for about 12 people and it was a smashing hit!! We drank Barbera with it and they were splendid!


  35. #
    Rachel Wilkerson — May 25, 2012 @ 12:28 pm

    F*ck, I am so excited to make this!


  36. #
    Kacie — May 25, 2012 @ 10:59 pm

    I’ve been reading your blog for months now and this is the 10th recipe I’ve made and OH MY GOSH. They have all been filed in the “to make again” folder but this one has become a staple meal in my kitchen. Thank you!


  37. #
    Kevin (Closet Cooking) — May 28, 2012 @ 4:11 pm

    Those grilled cheese sandwiches look amazing!


  38. #
    Tim — June 3, 2012 @ 7:23 pm

    This recipe was AMAZING! We tried it for dinner and now it is a family favorite.


  39. #
    Katie @ OhShineOn — June 5, 2012 @ 10:07 am

    Holy crap. Diggin’ THIS to the point of obsession.


  40. #
    Rosie — June 8, 2012 @ 8:38 pm

    Just made this. Again. My god. It is just so good. I make caprese panini often buy this recipe elevates the meal so much. Me + this panino = true love. The truest ever.


  41. #
    Katie — June 13, 2012 @ 2:21 pm

    I just made this for lunch and it was delish! I did a couple things different. First, I broiled the tomatoes instead of roasting to save on time and I don’t think it affected the flavor one bit. I buttered the bread before grilling instead of using the olive oil and that may have been a mistake. I think it made the bread a bit more absorbent for the balsamic glaze – resulting in a soggier sandwich. Overall, the flavor was fabulous!


  42. #
    Leila — June 19, 2012 @ 1:59 pm

    Seriously, you take the most droolworthy photos. I’m pretty certain you could make TRASH look delicious.


    • Kelly — June 20th, 2012 @ 1:15 pm

      You are not kidding. Everything she photographs I want to devour.


  43. #
    Coco — June 20, 2012 @ 12:16 pm

    Looks divine, esp the balsamico. YUM


  44. #
    Kelly — June 20, 2012 @ 1:16 pm

    WOW. Love your taste. You don’t get a better summer recipe than this.


  45. #
    Mia — July 20, 2012 @ 1:35 am

    Made this (sort of) on an English muffin tonight. It was melty and gooey and delicious. Thank you!!!


  46. #
    Stacy — August 25, 2012 @ 5:01 pm

    Love, love, love


  47. #
    Holly — September 4, 2012 @ 10:04 pm

    Any suggestions on a side dish for this? Wanna make it for dinner this week~


  48. #
    Simonswalker — October 6, 2013 @ 2:58 pm

    Omg – I was looking at the coconut chicken fingers recipe and found this one by accident. It was destiny!


  49. #
    Lee-Anne — January 18, 2014 @ 2:03 pm

    I was so excited to make these for lunch for my hubby and I. They were so soggy, it was like eating a caprese bread pudding. It was so yucky :(

    I think next time, I’ll save time by broiling these till almost completely dried out, or scooping out the seeds first. So disappointed to eat a grilled cheese with a knife and fork and for it to be comepletely gluey :(


  50. #
    Ally — July 19, 2015 @ 8:07 am

    amazing cant wait to try this :) Clean 9 Cleanse



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