Your 2026 Vacation, Classified: Obvious, Classic, or Discreet
Plus: Jeff Bezos can’t get into a club, a new private members’ club opening date, Bronson van Wyck’s 300-person Ibiza Pharaoh’s Ball, a $100,000 US Open hotel package and a $723m divorce offer...
There comes a point in any conversation about summer when someone asks where you went, and the answer has a way of revealing considerably more than your coordinates. Saying you spent two weeks in Comporta lands differently than saying you were in Positano. Mykonos means something before you have even told anyone where you stayed. Saint-Tropez? Visions of you dancing on a table have already been conjured up, no matter how good your French accent may be.
Vacation destinations have always carried a certain amount of social information and cultural capital, but in 2026, with social media turning every summer into content, the distinctions feel more pronounced than ever. Some places have become so universally recognizable and heavily trafficked by the same international summer crowd, that they now fall squarely into the Obvious category. Others have been popular for so long that they have achieved the safer status of Classic (here’s looking at you, Newport and Porto Cervo). And then there are the places that remain Discreet, which does not necessarily mean unknown so much as requiring a little more knowledge, effort or reason for being there (hat tip to Point O’Woods, Sylt and Sandhaam).
Plum Sykes recently got at the same phenomenon in her Substack piece, “Why the ‘Cool Rich’ Adore Antiparos,” in which she distinguishes between Rich People and Cool Rich People by, among other things, where they disappear to in the summer. Her basic argument is that inconvenience has become a luxury of its own. RPS will add to this by saying places like Saint-Tropez and Southampton are almost too easy, while Antiparos requires flights, ferries, and enough logistical friction to thin the herd. (Although that is the problem with Discreet places—eventually someone writes about them).
None of these categories are fixed, which is why this is very specifically the 2026 version. Comporta has been inching toward Classic for years, and Antiparos is getting more attention by the week. Mykonos, after all, did not start out as Mykonos.
That is usually how it happens. A place starts with the people who know, then comes the wave of people who heard about it from them, and eventually everyone is going. Give it enough time, though, and some destinations manage to come out the other side as Classics. And that’s about when the NO INFLUENCERS signs start going up.
So you tell me: what else belongs where on this Venn diagram of Obvious, Classic and Discreet summer vacation destinations in 2026? Paid subscribers, chime in.
Plus: Jeff Bezos can’t get into the Indian Creek Country Club, a new members club delayed until 2028, Bronson van Wyck’s 300-person Ibiza Pharaoh’s Ball, natural diamond prices collapse, a $100,000 US Open hotel package, boomers spending the kids’ inheritance on luxury travel, a $723 million divorce offer, Anthropic’s CEO’s wife and her very unexpected résumé, Penn cracks down on application shortcuts, the secret off-market superyacht boom, and more.
