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Cas awoke early each day. 4:15 am, to be exact. His habit was wake up, check on Dean, check on Sam, check the rest of the bunker, Dean, Sam, and then start reading.
At 6:05, he checked on Sam and found Dean in the kitchen. Eventually, Dean learned to make 2 cups of coffee, one black and one with cream. They talked sometimes about a case, sometimes about either of their long, tiresome lives.
When Sam got up, usually around 8, Dean had breakfast and a case ready while Cas read. They'd discuss the case and pick a hunter from the network for it. They were too old to hunt now. Sam would call around and get their hunter or someone else to take it.
Their network of phones officially opened at 9:30 am to the hunters who needed help or verification that they were, in fact, whatever they said they were, but Cas was never out of hearing range. Dean and Sam's days varied, but Cas worked the phones from 9:30 am to 7:30 pm.
He'd then join Dean and sometimes Sam in the kitchen for dinner. They'd talk about the day, work at Dean's auto shop, and anything else that came to mind.
At 9, they'd go and watch TV or a movie, alternating who makes the kettle corn and who picks what they watch. They went to bed whenever they got tired, or at 11:30. Mostly 11:30.
Cas didn't know what Dean or Sam did after that, but he read until 11:55. He went to sleep at midnight.
The next day he'd wake up at 4:15. His habit was wake up, check on Dean, check on Sam, check the rest of the bunker, Dean, Sam, and then start reading. Occasionally, Dean or Sam will be gone the second time he checks.
The first few times this happened, Cas went crazy. It took both Sam and Dean explaining, together and separately, that they weren't used to following the same thing everyday, and they weren't planning on leaving him alone in the bunker.
Sam was on a jog most of the time, but sometimes he was in the library. He never adjusted to being old, and he constantly wanted something to do.
In front of Sam, Dean said that he was just making breakfast early. Later with Cas, he confessed that he still had nightmares and was either driving around or playing guitar in the woods.
Now when one of them is gone, Cas pushes away the feeling of despair and checks the library or calls Sam. Dean has started leaving a note on his bed for Cas, but sometimes he forgets. When that happens, he simply checks the hill or calls Dean.
While Castiel may not understand the Winchesters sometimes, he is still grateful that they let him stay.