I've only made a couple of trips ever. When I was fairly fresh out of school, I tried to get a job knowing that it required monthly travel to DC. I got the job and was super excited, but before the travel ever started, I was reassigned due to business needs. More recently, there were all of these plans and arrangements for me to travel to NYC every one to two months. The week before my first trip there, a senior person in my office decided that it would be easier for the NY people to regularly come to us and that was that.
Mrs. chum, on the other hand, worked for the state of Florida and traveled around the state every other week. They visited several geographic areas per trip and always made sure they scheduled such that they could stay in a hotel on the beach.