Yield: 4 to 6 servings
Sherry and tomatoes are meant to be together, and this soup is a great accompaniment to a gooey, cheesy sandwich. I like it semi-smooth, which makes it a little thicker than normal tomato soup, but blend to reach your preferred consistently. Add more or less Sherry depending on your taste-just make sure you give it enough time to cook to take out the alcoholic bite. Perfect use for your immersion blender, if you have one! Be careful with the red pepper flakes-a pinch is all you really need. I was a little heavy-handed the first time I made this and it really overpowered the soup.
1 tablespoon extra-virgin olive oil
1 tablespoon butter
1 small shallot, minced
2 small garlic cloves, finely minced
1 cup dry sherry, divided
One 28-ounce can San Marzano whole peeled tomatoes, crushed in a large bowl with your hands
1 tablespoon white sugar
Pinch of red pepper flakes
1/2 cup whole milk or cream
1 tablespoon Sherry vinegar, or more to taste
Heat a Dutch oven over medium heat. Add the olive oil and the butter and allow to heat. Add shallots, sprinkle with salt and sauté for 6 to 8 minutes, until softened and very lightly colored. Add garlic and sauté for 1 minute, until garlic has softened slightly. Add 3/4 cup Sherry and allow to reduce for about 1 minute. Add the tomatoes and sugar and stir together. Season with salt and both peppers; tomatoes need tons of salt, so be generous and taste often. The longer it cooks, the more you need to taste and re-season. Bring soup to a simmer over medium heat. Reduce heat to medium-low and simmer for approximately 20 minutes. Add the milk or cream (this would be a great time to start preheating your oven and skillet for your sandwich!) and simmer for another 5 minutes. You can prepare your sandwich in the meantime.
Add the remaining 1/4 cup Sherry and simmer for 5 minutes. At the very end of the cooking time, add the Sherry vinegar and stir to combine. Taste one more time for seasoning and adjust accordingly. Blend to your desired consistency, or serve as is. Drizzle with a little cream or make some basil oil and make pretty swirls on top (it’s not as easy as it looks!).