Grilled Cheese with Pesto

This grilled cheese is next level good. I started whipping up these jazzed-up sandwiches when my basil went crazy last summer and I had way too much pesto on hand. When you bite into that melty mozzarella with the tangy pesto, sweet tomatoes and crunchy sourdough, it's mind-blowing. I've brought these to everything from casual backyard get-togethers to lazy weekend lunches, and everyone goes totally silent during that first bite, then looks up shocked like I've done something truly special in the kitchen.

My friend Dave, who can't cook to save his life, made these after watching me once. He texted me the next day: 'Man. My girlfriend thinks I'm amazing in the kitchen now. I'll buy you drinks next time.' That's what makes this sandwich so great - it looks impressive and tastes fantastic, but anyone can pull it off.

Tasty Ingredients

• Sourdough bread - Skip the flimsy white bread for this one. You'll want something with substance and a nice crust. I grab mine from a nearby bakery, but any decent sourdough does the trick.
• Basil pesto - Making your own is awesome if you can, but the fresh stuff from the cold section at the store works too. Just try to avoid those shelf-stable jars because they never taste quite right.
• Fresh mozzarella - Get the kind that comes as a ball in water. That pre-shredded or block stuff won't melt properly. Remember to dry it off before using so your sandwich doesn't get wet.
• Ripe tomatoes - During summer, I go for heirloom tomatoes from local markets. In colder months, I find Roma or campari tomatoes taste better than those bland, mushy beefsteak ones.
• Bacon - You don't need it, but it takes things up a notch. The smoky flavor balances the rich cheese and adds some extra crunch. And using a bit of that bacon fat for cooking? So good.

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Cooking Steps

Cook your bacon right

Start with a cold pan for bacon that stays flat. Let it cook on low heat until it's just how you want it - I like mine crispy but not burnt. Keep that leftover bacon fat in the pan for cooking your sandwich later.

Put it all together

Spread pesto on the inside of both bread slices - enough to taste good but not so much that it oozes out. Then add your mozzarella slices, tomato slices, and bacon if you're using it. Top with the second slice, pesto-side facing in.

Get your butter ready

Use real butter, soft enough to spread without tearing the bread. Cover the outside completely, right to the edges. Don't worry about calories now.

Medium heat is best

Keep the heat around medium. Too high and you'll burn the bread before the cheese melts. Too low and everything gets soggy. You should hear a gentle sizzle when the sandwich touches the pan.

Time to turn it over

Before flipping, butter the top side while it's still facing up. Then slide your spatula under it and flip confidently - if you hesitate, things might fall apart. After flipping, I sometimes press down slightly with the spatula to help everything cook evenly.

Let it rest

Wait a minute after cooking before cutting. I know it's hard with that amazing smell, but cutting too early means hot cheese running everywhere except into your mouth. Just wait a minute. It's worth it.

When my college-aged nephew stayed with me last year, I made these for lunch. This kid usually downs food without even tasting it, but he paused mid-bite and said, 'This is way better than the $14 grilled cheese they sell near my dorm, Aunt Jess.' Coming from a teenage boy who usually just grunts at me, that was huge.

Perfect Pairings

I always enjoy this with a basic tomato soup - it's a classic combo but way better. For dinner, I'll add a simple green salad with just leaves, olive oil, lemon, and some sea salt to balance out the richness. When I'm feeling extra, I'll open some crisp white wine - a Sauvignon Blanc works well with the pesto flavors.

Fun Variations

I sometimes use arugula pesto for something more peppery, or try fontina cheese for a different flavor. Swapping prosciutto for bacon gives it more of an Italian twist. During peak tomato season, I'll often keep the tomatoes out of the sandwich and serve thick slices on the side with just oil and salt - keeps everything from getting too wet.

Storage Tips

Let's be honest - these taste best right after cooking. But if you need to make them for a group, you can get all your stuff ready and just put them together before cooking. Or you can build them earlier (leave the tomatoes out though), wrap in foil, and stick them in the fridge until needed. Just let them warm up for about 15 minutes before cooking.

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Clever Tricks

• Mix some grated parmesan into your butter before spreading on the bread for an even crunchier, tastier crust
• If your tomatoes are really juicy, put the slices on paper towels for a bit before adding them to your sandwich
• For something really decadent, mix a bit of pesto into your softened butter before spreading it on the outside of the bread

I've been cooking for more than twenty years now, and there's still nothing quite like a perfect grilled cheese. This pesto version has become my go-to - the thing everyone asks me to make when they visit. It hits that sweet spot between familiar comfort food and something special enough to impress. And it always takes me back to summer days with my garden in full bloom, even in the middle of winter.

Frequently Asked Questions

→ Can I swap out the cheese?

Of course! Provolone, fontina, or whatever Italian-style cheese you like will taste great with pesto.

→ What can stand in for bacon?

Try using prosciutto, pancetta, or just skip it for plant-based sandwiches.

→ Is homemade pesto better?

It sure is! Blend fresh basil leaves, nuts, parmesan, garlic, and olive oil to make a zesty pesto at home.

→ What’s a good side dish?

You can’t go wrong with a cup of tomato soup. Or try a small green salad or even minestrone.

→ Can I get this ready ahead?

You can pre-cook any bacon you need, but wait until it’s time to eat to grill the sandwich fresh!