Insider Secrets Exposed: Scandals, Outrageous Requests, And Celebrity Drama From Private Resorts For The Ultra-Wealthy

Private members club resorts have evolved from exclusive enclaves into destinations that cater to travelers seeking both luxury and privacy. They frequently offer high-end amenities and personalized service – along with the exclusivity of not being open to anyone willing to pay the room rate (let alone redeem points).

The concept began as country clubs, which originated in Scotland, and began appearing in the U.S. in the 1880s as private clubs that offered recreational sports, often golf, tennis, and swimming, with facilities for dining and social gatherings. Typically located in suburban or rural areas, these clubs required expansive grounds, distinguishing them from urban athletic clubs.

The rise of country clubs in the United States was tied to suburbanization and the growth of upper-class elites, peaking between 1880 and 1930. The Brookline Country Club, founded in 1882, is recognized as the first U.S. country club, and there was a boom in the 1920s. Clubs initially focused on equestrian sports but shifted towards golf in the 1980s. Historically, country clubs were exclusive and often enforced racial, ethnic, and religious restrictions. Legal pressures in the 1960s forced the removal of discriminatory policies.

Many have lodging that members have access to. Resorts and vacation destinations, though, combine membership with full hotel products.

A five-year employee of a private resort “for the rich and famous” who worked in food and beverage answered questions online about their experiences and the things that they overhead working. They envied the lifestyles of wealthy guests, and found famous guests to often be paranoid and guarded – and would often visit alone (cherishing the space).

  • Nightmare Guests: A country music singer called a bartender a “butterface” and poured an expensive drink on the carpet to brag about his wealth. He was banned.

    That’s distinct, it seems, from the worst guest whom this individual says was referred to as the “biggest scumbag” but doesn’t elaborate as to why.

    Also, a group of guests threw shoes at taxidermy, drove a golf cart into a lake, broke into the bar, stole liquor, and caused over $20,000 in damages.

  • Juiciest Overheard Comment: “Who cares if it was insider trading? I made over 40 million dollars off that deal, sue me!”

  • Best Celebrity Encounter: Michael Jordan was described as polite, considerate, and took good care of the staff. Tipped adequately, though not as extravagantly as others.

  • Unusual Activities: There was a mysterious clearing in the woods near the owner’s house, which created a feeling of a “conspiracy,” but its purpose remains unknown.

  • Wildest Incident: A well-known politician and friends consumed 17 bottles of Fireball in three days and engaged in “dildo wars” (capture-the-flag with suction cup dildos) on the golf carts. They found guests passed out on the golf course.

  • The guest they loved most: and they realize this will surprise many, but Tucker Carlson and Family whom they found to be kind and respectful, had genuine conversations with the staff, and showed interest in their lives.

  • Substance Use: While not everyone used drugs, some guests indulged in marijuana and cocaine, and staff minded their business.

  • Special guest requests: included slushy and espresso machines, rare alcohols, and an entire elk helicoptered in for one guest’s meals (leftovers were enjoyed by staff).

  • Weird Secret Society Events: An annual high-stakes event involved influential people making what were likely major business deals. The staff was also aware of “swinger” activities among some guests.


Credit: CostaTerra Golf and Ocean Club, Portugal


Credit: CostaTerra Golf and Ocean Club, Portugal

No one’s inviting me to join Conquistadores del Cielo. However, when I lived in DC I was a member of the Arts Club, which is located in the home where James Monroe lived while President of the United States when the White House was being restored after the War of 1812,

I think they were quite desperate for members at the time they accepted me, since the membership was rapidly aging. Dues were fairly modest, and it gave me access to the venue for events which was special. (Many years ago I invited readers to a book launch party that I hosted there.)

Otherwise my access to most spaces is going to come from cash, points, or leveraging benefits of status and credit cards. If I had the dollars and inclination I’d likely just stay at Aman properties, to be honest.

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

More articles by Gary Leff »

Comments

  1. A five-year employee of a private resort “for the rich and famous” who worked in food and beverage answered questions online

    Reddit AMA is rife with aspiring fiction writers making stuff up. Reddit, being an audience of life-inexperienced teenagers and basement dwellers, can’t tell fact from fiction. Those losers upvote anything that sounds juicy–veracity be damned.

    Venues for actual VIPs have all staff sign ironclad nondisclosure agreements. Confidentiality is ingrained in their service culture, and service providers are remunerated handsomely to maintain the level of discretion expected in such venues. In short, plebs and peons will never hear the real story of anything related to real VIPs.

    So what do you do if you really want to know what goes on? You have to become a member yourself. You cannot trust what is written on the internet.

  2. To the article about guest at resorts? What Lib Bull Shit! To say u might be surprised that Tucker Carlson & his family were nice and kind?
    All the people I know say that when they meet lib politician’s, ,and loons are the most Rude
    Entitled people around.

  3. Tucker Carlson, the same nut job who claimed he was attacked by a demon in bed and worships a multiply convicted felon?

  4. @ SFO/EWR — Please, tell us what a bunch of entitled a**holes do in their ultra-wealthy private luxury retreats?

  5. Such a lovely bunch of comments, love how everything has to turn to politics regardless of the subject. Regarding Carlson, regardless of political views, we all know he has his public persona for the views, clicks and outrage, and then everything else, where it turns out he’s kinda normal (albeit, private country club ‘normal’).

    As for the country clubs, they attract all sorts, the only commonality is you need to be rich, and have someone to vote you in. Outside of that, of course there’s stories, just like there is in all walks of life, and unless you’re senior staff, as opposed to the seasonal staff, then who cares about the NDA? Not you’re 21 yr old getting paid $15 an hour and missing out on most the tips.

Leave a Reply

Your email address will not be published. Required fields are marked *