Along the lines of what Jim said, some people get to a point where they have more money and time off than they have desire to hash out the details. Work hard, play hard.
That's Backroads Bicycling's whole business model. The clients pedal the miles, with the company arranging the route, lodging, mid-day meals, sag wagon, etc. Of course you could do it far cheaper on your own, but the support, and comfort that someone knowledgable has planned it all is worth something for some people.
My cousin scouts locations in India for well-healed travelers who want an arranged tour that is off the beaten path. They get a custom itinerary, in-region guides and drivers and pre-checked lodging. The local providers want future business so they are motivated to keep the clients happy.
National Geographic offers some very upper-end trips to adventurous locations around the world (I think they've only had one client die in Alaska this year). The one that sticks in my mind was $55,000 for 20 days around the world in a chartered 757 with sleeper compartments (so you'd wake up at your new destination) and guided by Jared Diamond (Guns, Germs, and Steel). A bit out of my price range, but my oldest friend and her husband get invited to trips like that by a rich friend.