Fixed my problem. now my selection process starts at the top and when it reaches the end I can press enter and it will bring me back to the top.
Here is the code:
Dim previousSelectedIndex As Integer = Me.SelectedItems(0).Index
If Me.Items.Item(previousSelectedIndex).Index = Me.Items.Count - 1 Then
Me.Items(0).Selected = True
Else
Me.Items(previousSelectedIndex + 1).Selected = True
End If