Travelling with sugar baby?

I have to come out and say that while I have considered travelling with sugar baby, and came very close to doing that once, I never have actually travelled. Would be very interesting to hear other people's opinions and experiences on this topic. Obviously one would need to know the other person quite well, in order to have a comfort level with them. Would we get the same room or separate rooms? After all we would spend at least a weekend together, so to keep things interesting we would need some down time.
I am planning two business trips this summer. One to NY the other to Chicago. Both trips are to network and catch up on old friends from a famous NY bank, who have now scattered to the winds.
Will probably fly in on a Saturday and stay for 3 or 4 days. would like to have business as well as pleasure on this trip. Let's just see how it goes. Play it by ear.