Milan is 6 hours ahead of Montreal
Best overlap: 8:00 AM to 12:00 PM in Montreal is 2:00 PM to 6:00 PM in Milan.
Target 8:00 AM to 12:00 PM in Montreal, which lands at 2:00 PM to 6:00 PM for the Milan side. A 4-hour overlap gives you a workable daily window; aim for earlier in it to avoid clipping the end of someone's day.