A luxury travel agent who plans vacations for the world’s most high-profile clients has detailed what it means to organize lavish trips for the ultra-rich – and the summer’s hottest destination.
Over a decade ago, Jaclyn Sienna India founded Sienna Charles, a boutique travel agency that provides one-of-a-kind vacation planning to the wealthy who spend over $500,000 in a single trip.
Since launching her business, the 42-year-old has mastered the art of treating mega billionaires and scores of celebrities to the most lavish trips – she’s even helped former President George W. Bush and popstar Mariah Carey to travel in style.
And Jaclyn has no plans of slowing down anytime soon. With business booming like never before, the lavish travel consultant has lifted the lid on how the country’s stars love to travel and where her wealthy clients are jetting off to this summer.
Jaclyn Sienna India plans vacations for the world’s most elite and detailed what it means to throw lavish parties and trips for the ultra-rich
With business booming like never before, the lavish travel consultant (seen with her husband) has lifted the lid on how the country’s stars love to travel.
In a lengthy interview with The Cut, Jaclyn talked about her wealthy clients and how she fulfills even their most outlandish requests.
Jaclyn started by explaining that she started in the travel advice business at the age of 18 when she moved to Philadelphia and got a job at a five-star restaurant called Le Bec-Fin.
She told the outlet: “I worked there for five years and it opened up the world to me. I was in love with the people who came in – they were beautifully dressed, riding in Rolls-Royces and ordering $5,000 bottles of wine.
This opened her eyes to the world of destinations and she soon found herself working at a local travel agency.
There, Jaclyn realized she wanted more, so she imagined a bigger trip – one specially curated – for wealthier clients.
That’s when she realized she was right and decided to start her own business to help the ultra-rich.
“So I started my company 16 years ago based on the philosophy of knowing the customer, knowing the product and providing them with everything they need,” the entrepreneur said.
She wanted her company to offer everything to the elite class and so created two separate membership forms.
Since launching her business, the 42-year-old has mastered the science of giving mega billionaires and scores of celebrities the most lavish trips – she even helped former popstar Mariah Carey travel to the luxury.
She also helped plan former President George W. Bush’s vacation (seen in 2006)
Most of its clients are based in New York, Dallas and Los Angeles, are between the ages of 55 and 75 and work in the technology sector.
‘We charge our customers $75,000 per year for unlimited travel and restaurant reservations. Then it’s $150,000 a year for unlimited travel, dining, and lifestyle. This would involve arranging spa appointments, recruiting housekeeping staff, helping clients build a home gym, whatever they need,” the 42-year-old said.
She explained that the first-tier membership was best for clients who still had their hands tied with work and needed someone to handle all their planning.
The second membership option is perfect for those who have a more opulent lifestyle and own multiple homes, which Jaclyn says means more “lifestyles to manage.”
The advisor explained that clients can contact her company at any time for anything travel or lifestyle related and that they will be “all hands on deck.”
And for Jaclyn, there’s no demand she can’t handle.
Speaking about what her clients ask her, she told the outlet: “‘How do I hire Taylor Swift for my birthday party?’ or ‘Is there a new face person in LA that you like?” There are no rules other than everything must be right now. We acknowledge receipt of all emails within five minutes.
“And all our customers are really nice. We don’t take any fools because the amount of work and support that goes into the background is really intense. But for me, no expectation is unreasonable.
Jaclyn said she keeps about 10 percent of each hotel she books, which she said is a lot when you’re booking multiple $30,000-a-night suites every month.
She explained that the top tier membership was best for clients who still had their hands tied to work and needed someone to handle all their planning (stock image).
Travel agent revealed she had already closed Versailles for dinners (pictured)
However, the agent admitted that the most important thing for her is that her clients are happy, because if they are happy, they keep coming back.
She explained that even if she can’t fulfill one of her client’s requests, but goes beyond the other “128” requests, she knows she has obtained a forever client.
As for what she’s achieved, Jaclyn confessed that anything can be booked – adding that it all depends on how much money you have.
The lavish travel advisor told The Cut: “We closed Versailles for a private candlelit dinner. We have closed monuments in Türkiye. We had some really cool parties at the pyramids. We never really had to say no. It all comes down to money. It’s the cost. How much do you want to spend?’
On her website she offers things like “private yacht in Dubai”, “morning with the monks” and “Bhutan by helicopter”.
And when a customer asks for something that doesn’t exist, Jaclyn reveals that she often redirects them to a different activity or location that she deems better suited to their needs.
To access restaurants that are booked, Jaclyn admitted “you have to know someone at the restaurant and have a relationship with them.”
She also said she threw parties at the Pyramids (pictured).
She admitted that her wealthy clients have left Capri and are now looking for a more “unique” experience in Sicily (pictured).
Jaclyn also gave details of the travel tips the mega-rich will be following this year.
She said most A-listers put a “FedEx tag” on their luggage and ship it ahead of time to arrive at their destination so they don’t have to lug it through the airport.
“Another trend I’m seeing is that rich people don’t eat out as much as we think. They have their own leaders who travel with them so they can diet or track their medical or health goals,” she added.
And if you really want to travel like the ultra-rich, Jaclyn shared where they’re headed this summer.
She admitted that her wealthy clients have left Capri and are now looking for a more “unique” experience.
“They tour Sardinia by yacht or go to smaller islands in Sicily. Many extremely wealthy guests don’t even stay in hotels anymore. I find that many hotels are not conducive to a true high net worth situation.
“They have this trophy penthouse, the $30,000-a-night suite, but there’s a lot of work to do to get things up to what the client is used to. People want a certain type of water, or certain foods, or a dark, seven-bed room for their dog,” she told the outlet.
The lavish travel agent also said that more and more members of the super rich are avoiding hotels and instead staying on yachts (stock image)
And with the mega-rich no longer staying in hotels, Jaclyn revealed that villas and yachts have become the new go-to places to stay.
Luckily, Jaclyn even gave advice to “normal” people on how to travel. She explained that if you don’t really have the funds, you shouldn’t rely on the social media profiles of the mega-rich and instead find a place that fits your budget.
Although dealing with billionaires was an art, Jaclyn admitted that growing up, she wasn’t rich. However, she knew she was “born to be a billionaire.”
She told the outlet: “I started working when I was 13 because I wanted my own money. I always wanted things to be special. And that’s what I expect from everything I do: I want excellence. It doesn’t always have to be expensive, it just has to be good. I must have been a princess or something in my past life.
Additionally, she revealed that when she goes on vacation, she pays for everything herself, instead of getting reimbursed.
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