Inside the billionaire travel club: meet the luxury concierge who rented an island for Mariah Carey

Yahoo

12-07-2025

What plans have you made for your next holiday?
Breakfast atop the Arc de Triomphe, or perhaps private dining amid the splendour of the Palace of Versailles? How about an intimate tour of the Great Sphinx of Giza?
It's all in a day's work for the luxury travel concierge Jaclyn Sienna India, who has devoted her career to masterminding incredible experiences for her high-net worth customers.
"We do all the crazy stuff," Jaclyn tells HELLO! in our exclusive interview, speaking from her new home in Beverly Hills.
"We shut down monuments; we work with the most exclusive clients."
The founder of her own bespoke travel company, Sienna Charles, Jaclyn, 43, is the woman the ultra-wealthy turn to for premium out-of-reach experiences.
She once rented an entire private island in the Caribbean to host a birthday party for Mariah Carey.
Membership of Sienna Charles starts at $50,000 a year – and there's a long waiting list.
"I'd say we don't have any members now who are worth less than $500m," she tells us. "Probably 90% of our clients are billionaires."
'You can't just be a travel agent anymore. You have to know the hottest places, because when a client books that trip, they start communicating it to friends. You need to know the restaurants before they do, and get them in. You can't sell something you don't have access to."
Jaclyn's secret weapon is her little black book, in which she records the hotspots she finds through her extensive travels.
The American businesswoman spends more than 200 days a year visiting between ten and 20 countries to vet locations and meet locals, so she can "discover places and experiences that simply aren't found through conventional searches".
"The UK, France, Italy and the US are our top four destinations," she says.
"Japan is really popular, and skiing in the French and Swiss Alps… then, in awards season, it's Los Angeles, London for art shows, Paris for dining. The summer is the south of France, Italy and Greece."
'In the UK, it's London for private viewings of the Crown Jewels, access to private art galleries, dining at Michelin starred restaurants and VIP shopping experiences. Then it's the countryside, with experiences like falconry, horseback riding and farm-to-table dining."
High-net-worth individuals are using services like Jaclyn's to ensure their lives run seamlessly, wherever they are.
And it seems that no request is too big for Sienna Charles.
"We've travelled with tonnes of celebrities and booked trips for them, and the ask is always the same – privacy," Jaclyn says.
Think private meals at Louis Vuitton's historic home in Paris, or breakfast with the Hermès and Fendi families, also in the French capital – experiences that are out of reach for most people.
One high-profile client of Jaclyn's was the former American president George W Bush.
"We organised a remarkable visit to Ethiopia's Omo Valley for President Bush, his wife, four friends and 30 security agents," Jaclyn says. "We collaborated with local partners to custom-build a luxury camp specifically for his stay. We also added personalised touches.
"The Secret Service very rarely comes out of their approved list – they have to really want to work with somebody like me – so having that glimpse into the government was really special."
There is always a way to fulfil a client's wish, she says.
"If somebody wants Super Bowl tickets the night before, how much are you willing to pay for it? You can always get it done."
Born and raised in Brooklyn, New York, Jaclyn now splits her time between her homes in LA, New York and Paris – and she finds her client base fascinating
"People think differently when they have that type of money," she says. "Our clients often approach life and travel with a distinct mindset. It's not just about what they can afford, but how they prioritise and value their time and experiences.
"Many of our clients are what we call Type A personalities, accustomed to efficiency and excellence in all aspects of their lives.
"Whether it's deep-sea fishing in a remote ocean or attending an exclusive art auction, their passions inform their travel choices, and they are willing to spend sometimes up to $500,000 on a trip to make it special and memorable."
Jaclyn's own story began when she studied art history at Temple University, Philadelphia, and worked at the five-star French restaurant Le Bec-Fin, where its extremely wealthy diners would often spend $5,000 on a meal.
"They would talk about where they ate in Paris or New York or London. I would literally save the list, run there and be like: 'Wow, you could tell the difference.' They had such a standard."
After graduating, Jaclyn spent time travelling before setting up her agency in Palm Beach, Florida, in 2007, together with her husband, Freddy Charles. An expert in restaurants, wine, art, fashion and history, Jaclyn tells us that her company's unique selling point is herself.
"The differentiating factor is me, because of my taste level, my connections and my know-how of how to get it done, over and over again," she says.
So, what do her clients want right now?
"People are not taking vacations," Jaclyn says. "It's part of this new wealthy lifestyle. They live in four homes every week: there's a new social calendar. They're going to a winery for the harvest or to a fashion show, and they're moving around quite nomadically."
Her own destinations of choice include Bali, Hong Kong and Korea.
"I love Asia," she says. "My brother lives in Vietnam, so every year I take an apartment there for two months, and my husband and I rent a motorbike and are very much a part of the culture there."
There's no doubt that Jaclyn is a one-off powerhouse, and she isn't slowing down.
"I love learning – new places, new hotels," she says. "There's always a new restaurant, always a new designer. There's always something new."