When you spend your travel dollar, spending more will buy you not only a more comfortable product, but it also buys you a different social situation. In other words, you'll be sitting with people that don't mind spending three times the price to get to the same place as those in the cattle section. But the purpose of this post was to explore the "other than air travel" things. For instance, if you go on a fancy package tour, you're not just getting all of the hotels, transfers, meals, and air-tight logistics, you're also getting people that don't want to deal with those travel details. Maybe they don't have time to manage the travel logistics. Or the patience.
Could it be that there's not only a reluctance to spend the money, but also a bit of discomfort in being in a social setting with people who spend money in a way that you've never done (until now)? Generalizing here, but my BIL's working class neighborhood is "way more fun" than my white collar neighborhood could ever imagine to be