Italian Sun Dried Tomato Pesto Grilled Cheese

Why Is My Italian Sun Dried Tomato Pesto Grilled Cheese So Good!
- I’ve been playing around with grilled cheese combinations for years, including my Italian garlic bread grilled cheese, and Italian flavors are my favorite.
- Italian cuisine is actually my favorite to cook (shhh, don’t tell my Russian roots), so I know how to balance these salty, tangy, and rich ingredients until they complement perfectly.
- The tangy sun dried tomato pesto (pesto rosso), salty prosciutto, and creamy fontina hit every flavor note in one bite, so nothing here tastes bland.
- This is a fast, easy lunch or dinner, but the flavor never feels like a shortcut.
- In 15 minutes, you get a sandwich that tastes better than what most restaurants and they would charge double the price.
Table of Contents
Ingredients Needed and Notes

- Italian loaf: I like to buy an unsliced loaf so I can slice it to my own thickness. Pre-sliced loaf often has slices that are too thin for a grilled cheese that’s packed with goodies. Thicker bread holds up better to the pesto and won’t get soggy in the middle.
- Sun dried tomato pesto (pesto rosso): Homemade sun dried tomato pesto has a deeper, fresher flavor than many jarred versions. It only takes 5 minutes to make and keeps well in the fridge, so it’s worth making a batch ahead of time.
- Prosciutto: This thin, dry cured Italian ham gets slightly crispy on the edges as the sandwich cooks and adds a salty contrast to the rich cheese and pesto. If you have extra, make some prosciutto and melon as an appetizer.
- Fontina cheese: Fontina melts beautifully and has a mild, buttery flavor that compliments pesto and prosciutto without overwhelming it. Get a block and slice it yourself if needed. If you need a substitution, use mozzarella or Monterey Jack cheese.
- Butter: use salted or unsalted as you wish and let your butter soften before using. Softened butter or a butter spread makes it easy to coat the bread evenly without tearing it.
How to Make My Sun Dried Tomato Pesto Grilled Cheese: Steps and Tips

1. Preheat the pan low and slow. Medium to medium-low heat gives the fontina time to melt before the bread scorches.
2. Make sure your butter is softened before spreading it on the bread slices. Cover each slice with a thin layer.

3. Spread an even layer of sun dried pesto on each bread slice on the other side from the butter.

4. Cover each pesto covered slice with fontina cheese slices, covering the whole slice evenly.

5. Spread prosciutto slices evenly on two of the cheese covered slices.

6. Add the grilled cheese halves to the pan, butter side down, and let it cook until the bottom is nice and golden, crispy and cheese is melted gooey. If you need to, you can cover the pan with a lid to help the cheese melt.

7. Once the cheese is melted, press the plain cheese slice on top of the prosciutto slice to close the sandwich. Give it a press to meld everything together but not too hard to where the cheese oozes out.
8. Resting is important! 5 to 10 minutes of rest on the cutting board lets the cheese set up so it stays inside the sandwich instead of spilling out.

Variations to Try
- Swap the cheese. Provolone, mozzarella, or a Monterrey Jack all work well in place of fontina.
- Make it vegetarian. Leave out the prosciutto and add a few extra basil leaves or a handful of baby arugula for a peppery bite instead.
- Try a different bread. Sourdough or a crusty ciabatta both hold up well if you don’t have Italian loaf on hand. Focaccia sliced in half will also be a fantastic bread choice.
- Add a little heat. A pinch of crushed red pepper flakes in the pesto layer brings some warmth to every bite.
Ways to Serve Pesto Grilled Cheese
This grilled cheese is hearty enough to stand on its own, but it’s even better with something to dip it in or a side to round out the plate.
- Try it with a bowl of classic tomato soup or creamy tomato bisque for the ultimate dip and sandwich combo,
- Or pair it with creamy mushroom soup for something a little richer.
- For a lighter side, a simple green salad, a Caesar salad, or a bowl of Parmesan dill potato salad all work well.
Storing Leftovers
It’s best to enjoy this grilled cheese fresh, right after it rests, since the bread loses its crispness once it cools completely.
- If you do have leftovers, wrap them tightly and refrigerate for up to 2 days.
- Reheat in a skillet over medium-low heat to re-crisp the bread and re-melt the cheese. Avoid microwaving, since it will make the bread soggy.

Sun Dried Tomato Pesto Grilled Cheese Recipe FAQs
Yes. Store bought pesto rosso works well here if you’re short on time, though homemade has a fresher, more balanced flavor since you control the salt and oil. Just make sure you like that store-bought pesto!
I always make grilled cheese fresh, but you can prep the pesto and slice the cheese ahead of time so assembly only takes a few minutes when you’re ready to cook.
Soggy bread usually comes down to wet filling, too much filling, or bread that isn’t sturdy enough for the job. Stick to a dense Italian loaf, keep the pesto layer even instead of piled on, and don’t skip the butter on the outside. If pesto has too much out, strain some of it off. Make sure the bread is not too thin.
This usually means the heat is too high, so the bread finishes browning before the fontina has time to melt through. Drop the heat to medium-low and cover the pan with a lid for a couple of minutes to trap heat and help it melt evenly.
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Sun Dried Tomato Pesto Grilled Cheese Recipe
Ingredients
- 4 slices of Italian Loaf 1/2 inch-3/4 inch thick
- 1/3 cup pesto rosso (sun dried tomato pesto)
- 3 oz prosciutto
- 7-8 oz Fontina cheese sliced
- 3 Tbsp butter or butter spread softened
Instructions
- Start preheating a large cooking pan over medium to medium-low heat while assembling the grilled cheese.(Don't set the heat too high or the bread will burn and the cheese won't have time to melt.)
- Spread softened butter on one side of each slice of bread.
- Spread even amounts of sun dried tomato pesto on the other side of each slice of bread.
- Divide the sliced of fontina cheese over the sun dried tomato pesto on each bread slice.
- Divide the prosciutto evenly among two of the slices coved with pesto and cheese.
- Place the bread into the preheated pan, butter side down.
- Let it cook until the bottom side is crispy and the cheese is melted. (To help cheese melt if the slices are thicker, you can cover the pan with a lid for a couple of minutes.)
- Once cheese is melted, place the slice with just cheese and pesto over the slice with prosciutto and press down. Take the grilled cheeses out of the pan and onto the cutting board.
- Rest the grilled cheese for 5-10 minutes before cutting. (Resting the grilled cheese first helps the cheese to cool down and stay in the grilled cheese instead of spilling out.)
Notes
- Storing: Best enjoyed fresh, but leftovers can be wrapped tightly and refrigerated for up to 2 days.
- Reheating: Reheat in a skillet over medium-low heat to re-crisp the bread and re-melt the cheese. Skip the microwave, since it makes the bread soggy.
- Cheese swap: Provolone, mozzarella, or a Monterrey Jack cheese all work well in place of fontina.
- Store-bought pesto: A jarred pesto rosso works fine if you’re short on time, make sure you like the flavor and that it’s not too oily.
Nutrition
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Disclaimer: Nutrition information shown is not guaranteed to be 100% accurate as most ingredients and brands have variations.