Preheat your oven to 400°F (200°C). Line two baking sheets with foil to make cleanup easier.
Lay the bacon strips on one of the prepared baking sheets, ensuring the pieces don’t overlap. On the second baking sheet, combine the cherry tomatoes with olive oil, salt, and pepper, tossing to coat evenly. Place both trays in the oven and cook for about 20 minutes, or until the bacon is crisp and the tomatoes are roasted and slightly browned.
In a small bowl, mix together the goat cheese and pesto until well combined. This creamy spread will add a tangy and herbaceous flavor to your sandwich. I like to use a fork to smoothly blend everything together.
Take one slice of toasted sourdough bread and spread it with the goat cheese and pesto mixture (from Step 3). Layer on the cooked bacon and roasted cherry tomatoes (from Step 2), followed by the fresh arugula. Place the second slice of toasted sourdough on top to close the sandwich. Cut in half before serving for easier handling. I find that letting the tomatoes cool for a minute avoids a messy sandwich.