Private Sleeper Cars
In the first half of the 20th century, business magnates such as J.P. Morgan owned private sleeper cars aboard which they enjoyed the finest cuisine and service as they traversed the country. Today, no such luxury exists aboard Amtrak where, the Empire Builder excepted, meals are prepared off-board and reheated for passenger consumption. But it turns out a few private companies have capitalized on train-buff nostalgia by offering private sleepers boasting private chefs. In certain instances, these private cars are attached to Amtrak trains (I don't know the specifics behind this arrangement); in others, they're attached to freight engines that have been leased. Wealthier train buffs might own their own car, and lease it out when it's not in use, but almost anyone of reasonable means could afford, perhaps with a little saving, to lease a room in a car (not an entire car, mind you) for a short trip. A Cincinatti-based company offers group trips to Chicago for shopping and to Michigan for sight-seeing. Such trips can cost as little at $200/day/person. Of course, these trains stop along the way--making the trips quite long in certain cases--and the cost doesn't include your requirements off-board, but nevertheless, if you're looking for a slightly off-beat, domestic vacation, private sleepers might be just your ticket.