Preheat oven to 400°F (200°C). Toss cherry tomatoes with olive oil and brown sugar. Spread on a parchment-lined baking sheet and roast for 20–25 minutes, until blistered and jammy. Let cool.
While the tomatoes cool, combine water and honey (or sugar) in a small saucepan. Bring to a simmer, then add basil. Turn off the heat and steep for 10 minutes. Strain and cool.
In a blender, combine roasted tomatoes, milk, cream, honey, vanilla, and salt. Blend until very smooth. Taste and adjust sweetness if needed. Pour into a Ninja Creami pint container and freeze for at least 24 hours.
Place the frozen pint into the Ninja Creami and run the Ice Cream or Gelato setting. Scrape the sides and Respin if needed for extra creaminess.
Create a small tunnel in the center of the gelato and pour in the cooled basil syrup. Gently swirl using a spoon handle or chopstick—just enough to marble it through without fully mixing.
Scoop into small bowls and garnish with a cherry tomato slice, basil leaf, or a sprinkle of flaky salt for an elevated finish. 🍽️ This one is amazing with a side of crusty sourdough or as a palate cleanser between courses!