Grown-up Grilled Cheese with Sherry Tomato Basil Soup


Who doesn’t love grilled cheese and tomato soup on a cold wintery day? If you don’t, we probably can’t be friends. This grilled cheese is a result of LOTS of experimentation. I have a bit of a reputation because of these – and countless requests to finally get it posted. So here you go… now you can stop bugging me make your own whenever you like!

The soup recipe comes from the one and only Pioneer Woman. I mean, she puts sherry and cream in it. She can definitely be my friend.

Ingredients for Grilled Cheese

  • Any bread that can stand up to some weight. I personally love sough dough bread.
  • 1 slice of TWO of your favorite cheese (2 slices total – swiss ,cheddar, gruyere, etc)
  • 1 tablespoon whipped cream cheese
  • 1 tablespoon grated parmesan
  • 1 tablespoon butter

Ingredients for Soup
  • 1 medium sweet onion, diced
  • 6 tablespoons (3/4 stick) butter
  • Two 14.5-ounce cans diced tomatoes
  • One 46-ounce bottle or can tomato juice
  • 3 to 4 tablespoons sugar
  • 3 chicken bouillon cubes
  • Freshly ground black pepper
  • 1 cup sherry, optional – but seriously – do it.
  • 1 1/2 cups heavy cream
  • 1/4 cup chopped fresh basil
  • 1/4 cup chopped flat-leaf parsley


Preparation for the Soup (I suggest doing the soup first or even the day before)

  • Melt the butter in a large pot or Dutch oven and cook onion until translucent.
  • Now dump in the diced tomatoes and stir to combine. Add the tomato juice.
  • Add 3-4 tablespoons of sugar (add 3 and taste. Adjust accordingly – this offsets the acidity of the tomatoes).
  • Add 3 chicken bouillon cubes
  • Add the freshly ground black pepper.
  • Stir to combine, then heat almost to a boil. Then turn off the heat.
  • Add in the sherry
  • Stir in the cream.
  • Add the basil and parsley and stir.
  • Use an immersion blender if you have one and blend until smooth or your preferred consistency.  I like little bits of tomato in there but not super chunky.  If you don’t have an immersion blender, use a regular blender just be careful. Hot soup can explode the lid off if the steam can’t escape. remove center cap on lid and cover with a kitchen towel and then blend… start slow and build up to high speed. Again, until you reach your preferred consistency.

Preparation for the Grilled Cheese

  • Prepare all sandwiches first, then heat pan or panini press
  • Spread whipped cream cheese on one side of the bread. Layer the two slices of cheese and top with other piece of the bread.
  • Butter the outside of the sandwich and sprinkle with the grated parmesan. Do both sides of sandwich. You’ll get messy but so what – there’s a big reward coming!
  • If using a panini press then grill as normal
  • If using a frying pan or stove top grill: Put sandwich on HOT pan and cover with a lid to help melt the cheese. Flip after one minute and repeat. If your bread is getting too dark and cheese is not melted all the way – turn the heat down. You can also finish off in the oven if that is easier.
  • Cut in half and serve right away!

The Perfect Bite

Come on… you know what I’m going to say! Dip that sandwich into the tomato soup! That is seriously the most perfect bite ever.

The Perfect Pairing

I know you will probably be in shock, but I’m not feeling a beverage with this beautiful lunch. So I will suggest a different kind of pairing. Try adding a thin slice of tomato to your sandwich. Or a piece of prosciutto. Or a basil pesto spread. The sky’s the limit!

The Perfect Health

The vitamin K and calcium present in tomato soup can help you get healthy bones. Lycopene in tomato soup improves bone mass, fighting osteoporosis. Consuming tomato soup regularly reduces the blood levels of TNF alpha by 34%. Read more here.



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