Grilled Cheese with Sliced Tomato and Chipotle Mayo

With tomatoes ripening on the vines in my garden each day, I keep looking for recipes that use tomato (hopefully in abundance).

When I lived on the East Side of Milwaukee, Wis., I was within walking distance of this awesome coffee shop that served soups, salads and sandwiches for lunch. It was there that I fell head-over-heels in love with grilled cheese sandwiches. Don’t get me wrong, I always liked grilled cheese sandwiches. Really, really liked grilled cheese sandwiches. But I’d never before had anything on a grilled cheese sandwich besides cheese until finding this masterpiece made with chipotle mayo and sliced tomato.

Since it’s a pretty long commute from Oregon to Wisconsin, I have to recreate the sandwich in my kitchen. Luckily, it’s easy to do. Well, for most people it’s easy to do. I find grilled cheese sandwiches challenging to make at times. I somehow end up with burned bread and barely melted cheese. To ensure this doesn’t happen, I’ve taken to grilling the bread over medium-low heat. To facilitate the cheese melting process, I cover the pan.

Though you can make a delicious homemade mayo for this sandwich, I like to take a short cut.

mayoMix a little bit of mayo with some ground chipotle pepper. The more pepper, the bigger the kick.

My dad says my sandwiches are better than Alterra’s. That’s a compliment I’ll take any day.

We believe there are three fundamental rules for making a kick@ss grilled cheese sandwich. One – it should NEVER be made with American cheese (unless you’re making it for a child or an adult who eats like a child). Two – you cannot skimp on the cheese. Cheese should be dripping from the sandwich as soon as you plate it (and especially when you cut into it). Three – you gotta use butter. You just gotta. And you gotta use enough butter so that the bread isn’t dry. Who wants a grilled cheese sandwich that’s bone-dry on the outside?

Recipe rating: 

Food Snob

This sandwich is inspired by a sandwich I used to eat all the time at Alterra at the lake (now, apparently, called Colectivo Coffee). Their version, the Wisco Cheese Sandwich, uses cheddar, provolone, and pepper jack cheese.


  • 2 slices of your favorite bread
  • 3 or 4 slices of cheese (I used cheddar)
  • sliced tomato (fresh from your garden, if you have it!)
  • butter
  • chipotle mayo


  1. Slather two slices of bread with chipotle mayo (the more the better).
  2. Melt 2 teaspoons of butter over medium-low heat on griddle or frying pan and place two pieces of bread (non-mayo side down) on butter.
  3. Cover with 1 1/2 pieces of sliced cheese (or more or less if you prefer). Layer one piece of bread/cheese with sliced tomatoes. Cover and grill until cheese is melted.
  4. Flip non-tomato side slice over tomato side slice. Remove to plate. Cut, if desired, and serve.

I wasn’t…

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