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In a small saucepan, heat balsamic vinegar over medium heat until boiling. Reduce heat; simmer, uncovered, for 10 minutes or until vinegar is reduced to 1/4 cup. Set aside to cool.
Whisk together the olive oil and reduced balsamic vinegar.
In a large serving bowl or dish, layer tomatoes and onion. Sprinkle with salt and pepper. Drizzle with balsamic vinegar mixture. Marinate at room temperature for 1 hour. Top with fresh herbs.