tomato soup + a greeky grilled cheese

(might not be fall right now but It felt cozy) 🍅

I'm sharing this recipe in the middle of May—right between the end of soup season and the start of tomato season. But I happened to get my hands on a bunch of tomatoes, so I figured, why not make a cozy tomato soup? As always, I like to sneak in some Greek flavors when I can. Here, I added fresh oregano leaves and a splash of lemon juice (though you can swap the lemon juice for a drizzle of balsamic vinegar instead). Save this one for a chilly evening or whenever you find yourself with an abundance of tomatoes. Bonus points if you pair it with my Greeky grilled cheese below!

Ingredients:
5 pounds ripe tomatoes, quartered (roma, vine-ripened, or a mix with cherry tomatoes for sweetness)
1 large head of garlic, halved crosswise
1 large yellow onion, peeled and quartered
4–5 tbsp olive oil, plus more for finishing
Juice of 1 lemon or 1 tbsp balsamic vinegar
2 teaspoon salt, plus more to taste later
Black pepper, to taste
½ tsp red chili flakes (optional, for a kick-a little goes a long way here)
Pinch of smoked paprika (optional, adds depth)
2 teaspoon fresh oregano leaves (or 1 tsp dried)
1 small bunch fresh basil (stems for roasting, leaves for blending)
2 tablespoons tomato paste
½ to 1 cup heavy cream (for creaminess—use less if you prefer lighter)
3 to 4 cups vegetable or chicken broth (see notes below)
croutons or extra basil for garnish

Instructions:

1. Preheat oven to 400°F (200°C).
On a large baking sheet, toss tomatoes, garlic halves, onion, basil stems, and oregano leaves with olive oil and balsamic or lemon juice. Season generously with salt, pepper, and optional paprika and chili flakes.
2. Roast for 50 minutes to 1 hour, until tomatoes are collapsed and edges of the onions are caramelized and charred. Your kitchen should smell HEAVENLY!
3. Once ready, remove from oven and remove from basil stems. Squeeze the roasted garlic out of its skins.
4. In a large soup pot, heat 2 tablespoons of olive oil over medium heat. Stir in tomato paste and sauté for 2–3 minutes until it darkens and caramelizes slightly.
4. Transfer roasted vegetables and all their juices into the pot with the tomato paste. Add fresh basil leaves and 3 cups of broth. Tip: start with less broth and add as needed because you can always add but never take away!
5. Blend until smooth using an immersion blender directly in the pot (or transfer to a blender in batches). For a super silky texture, strain through a fine mesh sieve after blending (optional). I personally like a thicker texture so I don’t do this step.
6. Stir in heavy cream and bring the soup to a gentle simmer for 5–10 minutes.
Taste and add more salt or seasonings to your liking. If it’s too thick, stir in more broth ½ cup at a time until it reaches your desired consistency.
7. Serve hot with a swirl of olive oil and a few basil leaves. Serve on its own, with crusty bread or croutons, OR a grilled cheese! (recipe below for my Greeky grilled cheese)!

Texture reminder:
For thicker, cozier soup: use 3 cups broth and blend less.
For a smooth, sippable soup: use 4 cups broth, strain after blending.

🧀 Greeky Grilled Cheese

Tomato soup and grilled cheese go hand in hand—and just like I gave the soup a Greek twist, I did the same with this classic sandwich. I used a mix of feta and graviera or kasseri to bring in those bold, Greek flavors. Take it even further by adding sliced tomatoes, caramelized onions, or even a few kalamata olives inside.

Serves: 2
(Adjust quantities to your liking)