Bring a large pot of water to a boil. Once boiling, generously salt the water. Add in the pasta and cook to al dente, according to package directions. Drain the pasta, rinsing with cold water, and set aside. Meanwhile, as the pasta boils, prep the dressing. Add all listed ingredients to a high-speed blender. Blend until smooth and creamy. Set aside, or store in an airtight container in the refrigerator for up to 1 week.
Add the halved tomatoes to a large mixing bowl. Season with 1/2 teaspoon kosher salt, tossing to combine. Add in the bell pepper, red onion, kalamata olives, artichoke hearts, and cooked pasta. Pour the creamy Italian dressing over top. Toss to combine, seasoning with additional kosher salt & ground black pepper as needed.