Bill – Your best bet is to be in the 50-59 at your lower of the 2 handicaps. In your scenario, both of you in 50-59 at an 18 index. Playing the same courses, but not in the same foursome. The only way to play together in the same foursome is just for fun. You can’t play in two flights or on different courses just to be with someone. That’s the caveat to being able to travel together is reduction in age/handicap.