Oprah wins the award for “The Best Boss”. She took her entire Harpo staff and their families on an ultimate summer vacation on a Mediterranean cruise. Oprah and her staff were due to leave Chicago on Saturday and set to sail to Spain, Italy, Turkey, Greece and Malta. Oprah covered all costs which included transportation, food, drinks and activities at port stops. Chicago-based Best Travel reports that a cruise like the one Winfrey is taking her staff on costs about $5,400 a person. WOW!