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Preheat oven to 400ºF.
Drizzle inside of each squash boat with EVOO, and season with kosher salt and black pepper.
In a medium bowl, combine tomatoes, pesto, garlic, red pepper flakes, a drizzle of EVOO (about 1 to 2 Tbsp.), and a pinch of salt.
Place a wedge of feta cheese inside each squash half, followed by the tomato-pesto mixture, divided equally between each half.
Bake until the squash flesh is tender and the tomatoes burst, 50 to 55 minutes.
Use a fork to scrape the squash strands into the feta and tomato mixture, and continue mixing until everything is combined.
Garnish with fresh basil and extra cracked black pepper.