There have been many theories that the new class symbols have shifted from material goods to more unspoken rules of taste and exclusivity. Taking holidays in the same places is a crucial part of showing you belong to a certain community. Wealthy people are simply using travel as a way of strengthening their social class. They're essentially investing their finite holiday time in building social bonds with many people they already know or want to know closer. The benefits they get from being accepted by the class they aspire to be part of is far higher than what they might gain from a single holiday to a random-far flung location.
Travel is also a way people can immediately bond with others they're not very close with. When socialising, a lot of upper class people like to ask casual but very pre-determined questions to check whether you belong to their community. Obvious ones would be whether you ski, where you ski, which resorts you've been to, which ones were the best etc. If you cannot answer those questions, they're not interested. Being "well travelled" is pretty meaningless in their eyes and won't impress anyone during a dinner party conversation.
Several decades, being a world traveller was probably a status symbol. It showed you had the money, time, curiosity and a sort of courage to experience all sorts of new places. However I'd argue that backpacking culture, gap years and budget travel has taken the aura away from being able to travel the world. Social media has also cheapened exotic places because anyone can just watch a vlog on a trip to the the most obscure locations.
So in all honesty, it's no longer impressive to tell people you've been to X amount of countries. It often comes across as a bit smug and braggy to be honest. There are people who travel because they love it, and there are those who think that travelling makes them better people than others. It's easy to sniff out the smug travellers because they always want some sort of reaction to their stories or anecdotes.
The upper middle class know this and they're not interested in connecting with people who have just travelled all over. They're looking for people who have the taste and insider knowledge of which specific locations to go, and ideally ones with mutual friends in those holiday destinations.