Bring 2 quarts of salted water to boil in a 4 quart pot.
Add penne and cook for 8 minutes. Add broccoli and continue cooking for another two minutes.
Pour penne and broccoli into colander to drain and return pot to stove.
Heat pot on medium heat.
Add olive oil and bacon and saute' on low heat until bacon begins to brown.
Add garlic and stir for about 1 minute.
Combine milk and flour, ensuring that there are no lumps, and add to pot.
Bring to simmer, stirring continuously, until slightly thickened.
Add tomatoes and cheese and stir to incorporate.
Add pasta and broccoli and stir gently until pasta is cooked to desired doneness and sauce coats pasta.
Adjust seasoning and serve immediately.