My boss is likely traveling to Italy for approximately 10 days. He is not someone who collects CC points/Airline miles. His preference is to fly business or first class on a nonstop flight from New York City, preferably EWR, to any destination in Italy. He will need 5 seats for his trip.
1) What is the most effective way for me to assist him? I have found cash tickets with United priced at around $7,000 or 250,000 miles per ticket.
2) I understand the ethical considerations, but asides for brownie points and utilizing my spare time to learn new skills, are there any ways I can personally benefit from arranging his trip, such as earning points, gaining status, or accumulating miles?
I intend to have an open conversation with my boss regarding my goals, and he is not concerned if my efforts can help him save money.
(Please let me know if there is a better group to post this in)