Ham, White Cheddar & Roasted Tomato Grilled Cheese with Pesto Aioli

by Erin

Amp up your regular grilled cheese with the addition of ham, roasted tomatoes, and a pesto aioli.

Ham, White Cheddar & Roasted Tomato Grilled Cheese 3

I hope you enjoyed the smattering of Wedding-related posts I shared last week. If not, we are back to your regularly scheduled program of recipes. Today is an easy one because with all this rain and my stress levels at work I don’t have much time to do anything else.

I give you the longest grilled cheese name ever – ham, white cheddar and roasted tomato grilled cheese with pesto aioli (which would be awesome with some tomato soup on the side). I wanted to just called it a ham and white cheddar grilled cheese, but what makes it extra good are all those additional words so I left them be. Easy recipe, long name. Go figure.

Ham, White Cheddar & Roasted Tomato Grilled Cheese 1

I would like to point out that I used roasted tomatoes, not to be confused with sun dried tomatoes. Ever since discovering these delicious morsels at The Greater Gouda in Delaware, OH I’ve been obsessed. I might have an extra jar or two in stock in my pantry at all times just in case something happens. Also because I can’t make a jar last very long so I need back up or I will go through withdrawal.

The difference? Well they are roasted and thus softer than a sun dried tomato and taste much fresher. Kind of like a roasted red pepper, but it’s a tomato. Sure you could make this with sundried tomatoes if you can’t find roasted ones, but you could also make them yourself pretty easily I’ve heard but had yet to try myself to verify.

Ham, White Cheddar & Roasted Tomato Grilled Cheese 2

One year ago: Monthly Meal Plan: November

Two years ago: White Chocolate Buckeyes

Five years ago: Sweet and Sour Chicken

Six years ago: Scooter’s Spaghetti


Serves 1


1 Tbsp mayonnaise

1 Tbsp basil pesto

2 slices of good crusty bread

4 thick slices of deli ham

2 slices of white cheddar

8 roasted tomato quarters in oil, drained



  1. If you have a panini press, turn it on to warm up; otherwise, set a large skillet over medium heat.
  2. In a small bowl mix the mayo and pesto. Smear inside of bread slices with pesto aioli. Arrange a layer of cheese, ham, and tomato and top with second slice of bread, buttered side out.
  3. Place on preheated pan and grill until lightly browned, about 2-3 minutes. Flip over and continue grilling until cheese is melted. Slice and serve immediately.

Source: The Spiffy Cookie original

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