Whisk together the olive oil, rice wine vinegar, rosemary, and oregano in a large bowl. Add small and large tomatoes, and toss until evenly coated. Cover and refrigerate until chilled, 10 to 15 minutes. Season with salt and black pepper. Toss again before serving.
Since the sizes of heirloom tomatoes can vary, you may need to cut the bigger ones into 6 and the smaller ones into halves.
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