Okay, Let’s Talk Tomato Soup (and Grilled Cheese!)

Let me tell you, there’s just something about creamy tomato basil soup with grilled cheese that basically turns any gloomy day into a warm hug. I can still hear the rain from last Tuesday, the kind that smacks the windows, and I’m hustling to get dinner ready before the kids start their “what’s for dinner?” chorus. My mom used to make this on Sundays when we’d come in, cold to the bone, from the garden (or whatever muddy adventure we were on). And honestly, my first few tries were, um, let’s just say the blender and I weren’t on speaking terms for a week.

So now, whenever I make this, I can’t help but get a little nostalgic. Plus, there’s always a bit of kitchen chaos. Picture: soup bubbling over and me yelling, “Someone check the grilled cheese!” Only half-serious—because isn’t that half the fun?

Why I Keep Coming Back to This Soup

I make this when the weather’s grumpy, or when I need a reset after a week of questionable takeout. My family goes absolutely bonkers for it (even the one who claims to hate tomatoes). You know what’s funny? I used to think you had to roast the tomatoes first. Turns out, canned ones work surprisingly well in a pinch—my sister swears by it, though she’s always rushing somewhere. And, real talk, sometimes I sneak in a little extra cream just because it’s been that kind of day (King Arthur has a neat little explainer about cream in soups, if you’re curious). But truly, this recipe is the one I make when we all need a pick-me-up, or when my patience for fancy cooking is at an all-time low.

What You'll Need (With a Few Swaps)

2 tablespoon olive oil (Butter works too; I sometimes mix the two just for fun)
1 medium onion, chopped (Red onion if you’re feeling wild. Or really, whatever you’ve got rolling around in the fridge)
3 garlic cloves, minced
2 cans (28 oz each) whole tomatoes (San Marzano is the classic, but let’s be honest, store brand does the trick. My grandma always insisted on Muir Glen, but I think she just liked the label.)
1 ½ cups vegetable broth (Chicken stock if you’re not going for veggie-friendly)
½ cup heavy cream (I’ve used half-and-half, or even a splash of milk, when the fridge is looking sparse)
A good handful of fresh basil leaves (Dry basil in winter, but add it sooner so it flavors the soup better)
Salt and pepper (I never measure. Just taste as you go.)
For the grilled cheese:
— Sliced bread (white, sourdough, or that fancy rosemary loaf you bought and forgot about)
— Sliced cheese (Cheddar is my go-to, but mozzarella or something called "pepper jack" once snuck in and, well, wasn’t half bad)
— Butter (Margarine in a pinch. No judgment.)

How I Throw This Together (Plus Some Real Talk)

Heat the olive oil in a big ol’ pot. Toss in the onion (medium heat is fine; no need to get fancy). Stir till it’s soft—maybe 5 minutes. If you forget and it browns, it’ll add a little extra flavor (at least, that’s what I tell myself).
Add the garlic. About a minute is good. Don’t let it burn or you’ll have to start all over—except I once powered through and honestly, nobody noticed.
Pour in your canned tomatoes (juice and all) and broth. Here’s where I break up the tomatoes with a spoon, but sometimes I just use my hands—messy but satisfying.
Let the whole thing simmer, lid half-on, for about 20-25 minutes. This is when I usually realize I forgot to prep the grilled cheese. So, time to get those ready! (I usually just slap some cheese between bread, butter the outsides, and fry until golden. Not rocket science, but the secret is low-and-slow so the cheese melts before the bread burns. I learned that the hard way.)
Take the soup off the heat. Carefully blend it—if you have an immersion blender, awesome, but a regular blender works too. Just don’t fill it all the way or you’ll have tomato soup on the ceiling. Ask me how I know.
Return the soup to the pot. Stir in the cream and basil. Taste and add salt and pepper (and maybe a pinch of sugar if it’s too tangy for your taste).
Give everything a good stir and warm gently. That’s it! Now, grab your grilled cheese, slice it on the diagonal (because it just tastes better that way, right?), and dunk away.

Stuff I’ve Learned (Sometimes the Hard Way)

If you use low-fat milk, it’s fine, but the soup won’t be as rich. Not a big deal, but don’t expect miracles.
Fresh basil is amazing, but one time I used Thai basil and the flavor was... confusing. Not bad, just not quite right. Maybe save that for Pad Thai.
Cheddar melts better than Swiss, in my experience. One time I tried blue cheese and my family is still talking about it. Not in a good way.

Variations I’ve Actually Tried (And One I Regret)

Add a pinch of red pepper flakes for some kick. My husband says it’s “restaurant quality” (which, from him, is high praise).
Swap in coconut milk for a dairy-free version—tastes lighter and a little sweet, which is nice when I’m pretending to be healthy.
I added roasted red peppers once. Actually, I think it made the soup even better. On second thought, maybe I should do that more often.
One time, I tried putting pickles in the grilled cheese. Don’t do that. Just—trust me, it sounds funnier than it tastes.

Equipment (and Workarounds for the Rest of Us)

Large soup pot — Or whatever you’ve got that can handle a few liters.
Blender (immersion or regular) — If you don’t have either, you can mash the tomatoes with a potato masher and call it “rustic.”
Frying pan — Non-stick makes grilled cheese easier, but I’ve used a cast iron when the non-stick was “resting.”

Creamy Tomato Basil Soup with Grilled Cheese

How to Store It (If You Have Any Left)

Just pop it in a container in the fridge. I say it keeps for up to three days, but honestly, in my house it rarely sees sunrise. It’s even better the next day, I think—the flavors get a little cozier. The grilled cheese, though, is best fresh (but I have microwaved leftovers in a pinch, and it’s, well, edible). If you want freezer ideas, Simply Recipes has a nice guide that’s helped me avoid weird ice crystals in my soup.

How I Like to Serve It

Bowl of soup, grilled cheese on the side (cut on the diagonal, always). Sometimes I toss a few croutons on top, or even a sprinkle of Parmesan if I’m feeling fancy. If it’s Sunday, we’ll drag out the soup mugs and play cards after. It’s a bit of a tradition. Or, if I’m solo, I eat it standing at the counter, scrolling through my phone. Both ways work.

Some “Pro” Tips (aka: Learn from My Snafus)

Don’t rush the simmering step—one time I tried, and the soup tasted oddly raw. Give it at least 20 minutes; trust me.
Let the grilled cheese rest a minute before cutting. Otherwise the cheese goes everywhere, and not in the good way.
Actually, I find it works better if you blend the soup in batches rather than overloading the blender. Less mess. More soup in the bowl, less on your shirt.

FAQ (Because Folks Always Ask)

Can I use fresh tomatoes? Sure thing! You’ll want to peel and chop them, though. I’ve done it in the summer when the garden’s in overdrive, but honestly, canned is easier most of the year.
I’m out of cream. Now what? No worries! Milk works, or even skip it for a lighter version. I’ve even used Greek yogurt (add it at the end off the heat, or it’ll curdle, trust me).
What’s the best bread for grilled cheese? Whatever you like, really. Sourdough is chewy and lovely, but plain old sandwich bread is what I grew up with. I once tried a baguette and, well, it got a bit toothy.
Can I double the recipe? Absolutely. Just use a bigger pot and keep an eye on your blender—it’s easy to forget how much soup you’ve made until it’s dripping off the counter.
Is this gluten-free? The soup is, the sandwich isn’t—unless you use gluten-free bread. My cousin does and says it’s fine, but I’ve never tried it myself.
Do I need a blender? Not really. Potato masher, fork, or even just vigorous stirring works if you like it chunky. Rustic, as my aunt says.

So there you go! If you want to geek out about all things grilled cheese, Serious Eats has a whole page (that is, if you have time to fall down that rabbit hole). Anyway, if you make this, let me know how it goes—or what disasters you survived. Every bowl tells a story, right?

Creamy Tomato Basil Soup with Grilled Cheese