Miami is 6 hours behind Milan
Best overlap: 2:00 PM to 6:00 PM in Milan is 8:00 AM to 12:00 PM in Miami.
The overlap falls at 2:00 PM to 6:00 PM in Milan, or 8:00 AM to 12:00 PM if you're in Miami. You've got a decent 4-hour window. Set a recurring time near 2:00 PM in Milan (8:00 AM in Miami) and stick to it.