2 tsp. olive oil
1/2 tsp. Italian seasoning
Kosher salt
Freshly ground black pepper
Preheat oven to 375° and line a medium baking sheet with parchment paper. In a medium bowl, toss tomatoes with oil, Italian seasoning, salt and pepper. Cut bacon into thirds, then cut each third in half lengthwise. Wrap each tomato in a piece of bacon and secure with a 1/2 toothpick. Repeat until all tomatoes and wrapped in bacon. Bake until bacon is crisp, 25 minutes. Remove toothpicks and serve.