Pesto Grilled Cheese Sandwich

This ain't your mama's grilled cheese. I started making these fancy-pants sandwiches last summer when my basil plant went bonkers and I had pesto coming out my ears. The combo of gooey mozzarella, zippy pesto, juicy tomatoes and that sourdough crunch is flat-out ridiculous. I've served these at everything from backyard hangouts to lazy Sunday lunches, and people always go quiet for that first bite, then look up with wide eyes like I've performed some kind of kitchen wizardry.

My buddy Dave, who swears he burns water, made these after watching me do it once. His text the next day: 'Dude. My girlfriend thinks I'm a culinary genius now. I owe you beer.' That's the beauty of this sandwich - looks impressive, tastes amazing, but literally anyone can nail it.

Grab These Ingredients

• Sourdough bread - Don't mess around with wimpy sandwich bread here. You need something sturdy with a decent crust. I get mine from the local bakery, but any good sourdough works.
• Basil pesto - Homemade is killer if you've got it, but the stuff in the refrigerated section at the grocery store works fine. Just avoid the shelf-stable jars if possible - they never have that fresh punch.
• Fresh mozzarella - The kind that comes in a ball, swimming in liquid. That vacuum-sealed block stuff just doesn't melt the same. Pat it dry before using or you'll end up with a soggy situation.
• Ripe tomatoes - In summer, I'm all about heirloom tomatoes from the farmers market. In winter, Roma or campari tomatoes tend to have better flavor than those pale, mealy beefsteaks.
• Bacon - Optional but game-changing. The smokiness cuts through the richness of the cheese and adds crunch. Plus, cooking the sandwich in a bit of that bacon fat? Heaven.

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Making Magic

Get that bacon perfect

Starting with a cold pan is the secret to bacon that doesn't curl up. Let it cook slowly until it's exactly how you like it - I go for crispy but not burnt. That leftover bacon grease in the pan becomes your secret weapon for the sandwich.

Build your masterpiece

Slather that pesto on the inside of each bread slice - not too much or it'll squish out, but enough to taste. Then layer your sliced mozzarella, those gorgeous tomato slices, and bacon if you're using it. Cap it with the second slice, pesto-side down.

Butter me up

Real butter, softened so you can spread it without mangling the bread. Cover one outside surface completely, edge to edge. This is not the time to worry about calories.

Low and slow wins

Medium heat is your friend. Too hot and you'll burn the outside while the cheese is still cold. Too low and everything gets soggy. The perfect grilled cheese sizzles gently when it hits the pan.

The flip

Before you flip, butter the second side while it's facing up. Then get under it with a spatula and commit to the flip - hesitation leads to sandwich collapse. Once flipped, I sometimes press down gently with the spatula to make sure everything's making good contact with the pan.

The resting period

Let it sit for a minute after cooking. I know it's torture with that smell driving you crazy, but cutting too soon means molten cheese everywhere except your mouth. Just 60 seconds. You can do it.

When my nephew visited from college last year, I made these for lunch. This kid normally inhales food without noticing what he's eating, but he stopped mid-bite and said, 'Aunt Jess, this is better than the $14 grilled cheese at that place near campus.' Highest praise from a 19-year-old boy who normally communicates in grunts.

Serving Suggestions

I love this alongside a simple tomato soup - classic combo elevated. For dinner, I'll add a side salad with just greens, olive oil, lemon juice, and flaky salt to cut through the richness. If I'm feeling fancy, I'll open a bottle of crisp white wine - something like a Sauvignon Blanc that can stand up to the pesto.

Switch It Up

Sometimes I'll use arugula pesto for a peppery kick, or sub in fontina cheese for a nuttier flavor. Adding a few slices of prosciutto instead of bacon takes it in an Italian direction. In peak summer, I'll sometimes skip the tomatoes inside and instead serve thick tomato slices on the side with just olive oil and salt - keeps the sandwich from getting soggy.

Keep It Fresh

Let's be real - these are best straight from the pan. But if you need to make them ahead for a crowd, you can prep all the components and assemble just before cooking. Or build the sandwiches (minus tomatoes) earlier in the day, wrap in foil, and refrigerate until ready to cook. Just let them come to room temp for 15 minutes before hitting the pan.

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My Pro Tips

• Mix a little parmesan into your butter before spreading it on the bread for an extra crispy, flavorful crust
• If your tomatoes are super juicy, let the slices rest on paper towels for a few minutes before adding to the sandwich
• For extra indulgence, mix a little pesto into your softened butter before spreading it on the outside of the bread

I've been cooking for over twenty years, and there's still something magical about the perfect grilled cheese. This pesto version has become my signature - the thing friends request when they come over. It's that ideal balance of familiar comfort food with just enough of a twist to make it special. Plus, it reminds me of summer days with my garden in full swing, even in the dead of winter.

Frequently Asked Questions

→ Can I use a different cheese?

Absolutely! Provolone, fontina, or a mix of Italian cheeses would work well with the pesto flavors.

→ What can I use instead of bacon?

Try prosciutto, pancetta, or leave it out completely for a vegetarian option.

→ Can I make my own pesto?

Homemade pesto is fantastic in this sandwich! Use fresh basil, pine nuts, parmesan, garlic, and olive oil.

→ What's a good side dish with this?

Tomato soup is classic, but a light green salad or cup of minestrone would complement the Italian flavors.

→ Can I prepare this ahead of time?

You can cook the bacon ahead, but assemble and grill the sandwiches just before serving for the best texture and melty cheese.