Roasted Tomato and Pesto Grilled Cheese

Tomato-Pesto Grilled Cheese.

Tomato-Pesto Grilled Cheese.

This is day two of being snowed-in.  Sidewalk is shoveled, but driveway not plowed!   Go figure that one.  Snowplow guy seems to be busy elsewhere.  Well, there’s still plenty of food in the house, so no rush about going anywhere.

Under these house-bound conditions,  almost as soon as breakfast is over, I start thinking about lunch.   Wouldn’t you?  I’m imagining some kind of a grilled cheese sandwich.  Most folks love the combo of tomato soup and grilled cheese, so let me see if I can cram the two of them together in a knock-your-socks-off sandwich.  Get ready for an ooey-gooey delight.

First we’re going to go to our refrigerators to gather up all the delicious things we’ll need.  If those things should happen to be roasted, pesto-ed, or melty, that’s ideal.

Today I’m lucky, I have some good things.  This is not always the case.  Sometimes all I have in the fridge is skim milk and some bendy celery with brown tops.   That’s why there’s frozen pizza, right?  Skim milk and bendy celery are not allowed in this sandwich.   Absolutely not,  not when I see some precious Romano,  cheddar and pesto in there, not to mention some beautiful red tomatoes.


This is what it looks like to pack every delicious item in your refrigerator between toasted onion rolls.

(These are not the best photos I’ve ever taken, but I was too impatient to eat this sandwich.)

I’m the kind of person who likes to always have pesto on hand.  Quite some time ago I posted my recipe for homemade pesto(s), and I really recommend you make some for your refrigerator.  Made from herbs or spinach or kale (ignore that bendy celery),  you’ll thank yourself when you go looking in your refrigerator for some “good things”.  BTW, make lots–it freezes well, too.

On this sandwich we layer shredded cheddar, smeared pesto, roasted tomato puree, salty Romano cheese and mayo!


Roasting the tomatoes intensifies their flavor and sweetness.  The pesto adds a happy green, garlic-y kick.  Two kinds of cheese because we’re the kind of people who deserve two kinds of cheese on our sandwich.  Spread the top and bottom of the sandwich with mayo and grill on each side until the center is warm and melty.

The center gets melty and warm.

The center gets melty and warm.

Now the pay-off.   Take that sandwich to your favorite comfy place and settle yourself into coziness.  Sit down on the floor if you have to, just relax and enjoy it.  Now eat slowly and savor every delicious bite.    Relax.  Read your e-mails, or check out Pinterest.  Only move when the desire for some chips or a beverage motivates you beyond laziness.  Bendy celery, get outta here!



Yield:    Makes 2 sandwiches


  • 1 Tbsp. olive oil, divided
  • 4 plum tomatoes, halved and seeded
  • 2 garlic cloves, unpeeled
  • 1/2 tsp. dried basil
  • dash of salt and pepper
  • 4 tsp. canola mayonnaise
  • 2 Tbsp. pesto
  • 2 oz shredded sharp cheddar cheese, (about 1/2 cup)
  • 2 oz. Romano cheese, thinly sliced
  • 4 slices of whole grain bread or rolls of choice


1.  Preheat oven to 400*F.  Combine 1 tsp. oil, tomatoes, and garlic on a baking sheet.

Cut in half and seed tomatoes.

Cut in half and seed tomatoes.

Bake at 400*F. for 20 minutes.  Remove skins and discard. Squeeze garlic to extract the pulp, discard skins.

Roast with garlic.  Remove skins.

Roast with garlic. Remove skins.

2.  Combine tomatoes, garlic pulp, basil, salt and pepper in a mini food processor  pulse 10 times.

Place in mini processor and  chop finely.

Place in mini processor and chop finely.

3.  Spread mayonnaise on two slices of bread or top half of rolls. Spread pesto on remaining 2 slices bread or bottoms of rolls.

Spread mayo and pesto on bread slices.

Spread mayo and pesto on bread slices.

4.  Spread about 1 1/2 tablespoon tomato mixture on sandwich bottoms.  Cover with half the grated cheese on each bottom,  top that with thinly sliced Romano cheese.


5.  Cover with sandwich tops.  Lightly coat outsides of sandwiches with cooking spray.

6.  Heat a large skillet over medium heat.  Add 1 teaspoon oil, swirl to coat.  Place sandwiches in pan; cook about 3 minutes or until lightly browned.  Flip sandwiches, and continue to cook until lightly browned and cheese is melted.  Cut in half and serve immediately.

7.  If you have a panini pan, sandwiches may be cooked in that instead of a skillet.



SOURCE:  Carolyn’s Originals



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