Sun-Dried Tomato Tapenade Grilled Cheese

I went through a phase many years ago where I was on the hunt for the best grilled cheese sandwich. It kind of ended when I realized that all grilled cheese sandwiches are pretty good. This Tapenande Grilled Cheese with a homemade sun-dried tomato and olive tapenade has stayed one of my favorites though. 

The trick to making this sandwich delicious is obviously the homemade tapenade. In fact, I’ll frequently double the tapenade recipe and use it for all sorts of things! 

Good fresh mozzarella cheese is also nice in this sandwich. Just be careful not to over-melt the cheese as it can break down! 

Making the Tapenade

You could make a more traditional tapenade with capers and anchovies if that’s your thing. I went with a garlic and sun-dried tomato version though.

If you have the time, you can roast a head of garlic. This couldn’t be easier. Just chop off the top off an entire bulb, drizzle it with a bit of olive oil and a sprinkle of salt and wrap the whole thing in foil.

Bake it at 350 for about 30-40 minutes. Your house will smell delicious and the garlic should be a nice light brown color. Let it cool for a few minutes.

I’ve made this tapenade a few times over the years without roasting the garlic though and it works just fine. The benefit of roasting the garlic is you can add more garlic as it’s a milder flavor profile. 

An olive tapenade like this is easiest to make in a food processor although you can absolutely just chop everything together as well. I threw in my sun-dried tomatoes first as they would be the hardest to chop and gave them a spin for a few seconds. Then I added my olives and finally my cloves of roasted garlic. Drizzle in a few tablespoons of olive oil until the mixture comes together.

Bonus tip: If your sun-dried tomatoes come in olive oil, use a few spoonfuls of that oil in the tapenade for extra flavor. 

Pulse it a few times to combine everything and you’ll be all set. You don’t want to over-process this spread. A bit chunky is good in my book.

• Don’t like sun-dried tomatoes? Try my pesto and brie grilled cheese!

Making the Grilled Cheese Sandwich

I think that choosing the appropriate bread is one of the most important things you can do for grilled cheese. For this sandwich, I think I chose wisely. I went with a rustic loaf of sourdough although I’ve also made it with homemade no knead bread. 

You want to make sure you have something hearty enough to stand up to the tapenade.

To get the sandwich ready, take two slices of bread and lightly spread butter on them. That will be the outside of the sandwich. Then flip the pieces over and slather on some tapenade onto both sides of the bread. Layer on sliced mozzarella and some fresh basil and smash it all together so the buttered sides are on the outside!

It’s ready for the heat!

The key thing about a grilled cheese sandwich is controlling the heat. To hot and you’ll burn your bread before your cheese is melted. Too low on the heat and you’ll starve before it’s done.

A medium to medium-high heat should be about right depending on your stove and pan. Just set the sandwich in and let it cook for a few minutes and gently give it a flip. These aren’t like pancakes, you can flip them over and over again and that’s just fine.

This is about as perfect as it gets in my book:

The good news about this sandwich is that mozzarella melts incredibly fast. So you shouldn’t have to worry about the bread being toasted before the cheese is melted. In fact, the worry is that if you cook this sandwich too long, the mozzarella will OVER melt and just break down in your sandwich. Fresh mozarella is already very soft so just warm it up and it’ll be great. 

Here are a few other great recipes to try!

• Grilled Greek Steak Wraps
• Sun-Dried Tomato Orzo Salad
• Tapenade Grilled Cheese
• Artichoke and Olive Dip
• Jalapeno Popper Grilled Cheese from Small Town Woman