You need to reach a certain relationship level with every maid (Emily: 2, Leyla: 3, Mary: 2, Kate: 5), and be in your room in the afternoon to get the option "Take a walk with everyone (ends Chapter 1)".
Make sure you have followed the story hints of all maids until it says "There are no more story events for X in this version of the game."
If you're still not getting the option in the afternoon after that, we will need more information to figure out what is wrong.