Cook the pasta according to the package directions. Drain it, rinse under cool water and set aside in a large bowl.
Combine the mayonnaise and milk in a medium bowl, then add 2 tablespoons vinegar and stir until smooth. Add the chipotles in adobo sauce and 1/2 teaspoon each of salt and pepper. Stir the dressing until combined. Give it a taste and add more vinegar if you'd like it to have a bit more bite. Add more adobo sauce if you'd like it to have a little more heat.
Drizzle the dressing over the pasta, then throw in the tomatoes and cucumber and add the cheese. Stir the pasta around, then add the basil and stir until just combined. Taste and adjust the seasoning as needed, then cover the bowl with plastic wrap and chill it for at least 2 hours or up to 24 hours.
Transfer to a serving bowl and garnish with more basil.