As an optional step, roast the tomatoes. In a roasting pan or baking sheet, add the tomatoes and drizzle 1 tablespoon olive oil. Toss until evenly coated, and arrange in a single layer.
Preheat your oven to 200 degrees C (fan/air fryer 180 degrees c). Roast the tomatoes for 20 minutes, then let cool.
As another optional step, make shrimp-infused olive oil. In a skillet, add ½ cup of olive oil and the reserved shrimp shells. Turn on the heat to medium low and cook, stirring occasionally, until shrimp shells are deep red in color and the oil is aromatic, 10 minutes. Strain the oil, leaving about 2 tablespoons in the pan for making the pasta, and let cool. Discard the shells.
Now, make the pesto. In a bowl or food processor jug, add the tomatoes, garlic, tomato paste, parmesan, vinegar, and salt. Pulse until finely chopped and combined. It's ok if the pesto is a bit chunky.
While pulsing or running the blender on low, slowly stream in the olive oil, until it emulsifies and thickens.
Add the basil and pulse until combined. Set aside until ready to use.
Next, cook the pasta. In a large stock pot over medium high heat, bring the water to a rolling boil. Add the salt, and return the water to a boil.
Add the linguine and cook, stirring a little at the beginning to prevent from sticking, until al dente according to package instructions.
About 5 minutes before the pasta is done, make the sauce. In a large skillet over medium high heat, heat the olive oil.
Thoroughly pat dry the shrimp. When the pan is very hot, add the shrimp and sear, 1½ minutes.
Add the garlic, then flip the shrimp over. Continue cooking for another 1½ minutes.
Lower the heat to medium. Add the pesto and saute, stirring, about 1 minute.
Add the minced chipotle peppers, tomatoes, and stir to combine.
When the pasta is done, reserve about ¼ cup of pasta water, and drain in a colander.
Now add the linguine and reserved pasta water to the pan and cook, tossing to incorporate for 3 to 5 minutes.
Remove from heat. Stir in the chopped basil and toss to blend.
Serve immediately, topped with additional Parmesan, tomato slices, and basil leaves if desired. Top with toasted almond slices for a truly authentic pesto alla Trapanese pasta.