Portland is 9 hours behind Milan
Best overlap: 5:00 PM to 6:00 PM in Milan is 8:00 AM to 9:00 AM in Portland.
Target 5:00 PM to 6:00 PM in Milan, which lands at 8:00 AM to 9:00 AM for the Portland side. With only around 1 hour of shared time, be precise — book 5:00 PM in Milan (8:00 AM in Portland) and you'll catch both teams.