A luxury travel agent who plans vacations for the world’s most elite clients has detailed what it’s like to organize lavish trips for the ultra wealthy – and the destination hotspot of the summer.
Over a decade ago, Jaclyn Sienna India founded Sienna Charles, a boutique travel firm that offers one-of-a-kind vacation organization to the rich who splash out over $500,000 on a single trip.
Since she began her business, the 42-year-old has mastered the art of giving mega billionaires and a slew of celebrities the most opulent trips – even helping former President George W. Bush and popstar Mariah Carey travel in style.
And Jaclyn has no plans of slowing down any time soon. With business booming more than it ever has before, the lavish trip advisor has lifted the lid on just how the country’s A-listers like to travel and where her affluent clients are jetting off to this summer.
Jaclyn Sienna India plans vacations for the world’s most elite has detailed what it’s like to organize lavish parties and trips for the ultra wealthy
With business booming more than it ever has before, the lavish trip advisor (seen with her husband) has lifted the lid on just how the country’s A-listers like to travel
In a wide-ranging interview with The Cut, Jaclyn opened up about her wealthy clients and how she fulfills even their most outlandish requests.
Jaclyn started by explaining that she began in the travel advisement industry 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 my whole world. I was enamored with the people who came in — they were dressed beautifully, rolling up in Rolls-Royces and ordering $5,000 bottles of wine.’
This opened up her eyes to the world of destinations, and soon enough she found herself working at a local travel agency.
While there, Jaclyn realized that she wanted more, she imagined a greater trip – a specifically curated trip – for the most wealthy clients.
That’s when she realized she was onto something and decided to build her own company around helping the ultra-rich.
‘So I created my company 16 years ago based on the ethos of knowing the client, knowing the product, and providing everything they need,’ the entrepreneur said.
She wanted her firm to offer everything to the elite class so she created two distinct forms of membership.
Since she began her business, the 42-year-old has mastered the science of giving mega billionaires and a slew of celebrities the most opulent trips – with her even helping former popstar Mariah Carey travel in luxury
She has also helped plan former President George W. Bush’s vacations (seen in 2006)
Most of her clients are based in New York, Dallas and Los Angeles, are aged 55 to 75 and work in tech.
‘We charge clients $75,000 a year for unlimited travel and dining reservations. Then it’s $150,000 a year for unlimited travel, unlimited dining, and lifestyle. That would include arranging spa appointments, recruiting house 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 of their planning.
The second membership option is perfect for those who have more opulent lifestyles and boast multiple homes, which according to Jaclyn means more ‘lifestyles to manage.’
The advisor explained that clients can contact her company at anytime for anything travel or lifestyle-related and they will be ‘all hands on deck.’
And to Jaclyn, there is no request that she can’t handle.
Speaking about what her clients ask of her, she told the outlet: ‘”How do I hire Taylor Swift for my birthday party?” or “Is there a new facial person in LA that you like?” There’s no rules other than everything needs to be right now. We acknowledge all emails within five minutes.
‘And all our clients are really nice. We don’t take on any jerks because the amount of work and hand-holding that goes into the back end is really full-on. But to me, there’s no expectation that’s unreasonable.’
Jaclyn said that she keeps about 10 per cent from every hotel she books, which she explained adds up a lot when you are reserving multiple $30,000-a-night suites every month.
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 of their planning (stock image)
The travel agent revealed that she has previously closed down Versailles for dinners (pictured)
However, the agent admitted that the most important thing to her is that her clients are happy, because if they’re happy, they keep coming back.
She explained that even if she can’t fulfill one of her client’s requests, but goes above and beyond for the other ‘128’ demands, she knows she has secured a forever customer.
As far as what she has made happen, Jaclyn confessed that anything is bookable – adding that it all comes down to the amount of money you have.
The lavish travel advisor told The Cut: ‘We’ve closed down Versailles for a private candlelit dinner. We’ve closed down monuments in Turkey. We’ve done really cool parties at the pyramids. We’ve never really had to say no. It all comes down to money. This is 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 client asks for something that doesn’t exist, Jaclyn revealed that she often redirects them to a different activity or location she thinks is better for their expectations.
To get into restaurants that are booked, Jaclyn admitted ‘you have to know a person at the restaurant and have a relationship with them.’
She also said she has thrown parties at the Pyramids (pictured)
She confessed that her affluent clients are over Capri and are now looking for a more ‘unique’ experience in Sicily (pictured)
Jaclyn also dished out the details of the travel tips that the mega rich will be doing this year.
She said that most of the A-listers put a ‘FedEx label’ on their bags and ship them to arrive at their destinations ahead of time so they don’t have to lug them through the airport.
‘Another trend I see is that wealthy people don’t eat out as much as you think. They have their own chefs who travel with them so that they can stay on a diet or keep pace with medical or health goals,’ she added.
And if you really want to travel like the ultra wealthy, Jaclyn has shared the location that they are heading to this summer.
She confessed that her affluent clients have moved on from Capri and are now looking for a more ‘unique’ experience.
‘They’re taking the yacht around Sardinia or going to smaller islands in Sicily. A lot of extremely wealthy clients aren’t even staying at hotels anymore. I find that many hotels are not conducive to a real ultrahigh-net-worth situation.
‘They have that trophy penthouse, the $30,000-a-night suite, but there’s a lot of heavy lifting to get things the way that the client is used to. People want a certain type of water, or certain foods, or a bedroom that is dark and has seven beds for their dog,’ she told the outlet.
The lavish travel agent also shared that more and more members of the mega rich are skipping out on hotels and staying on yachts instead (stock image)
And since the mega rich aren’t staying at hotels anymore, Jaclyn revealed that villas and yachts are in and have become the new go-to spots to stay.
Luckily, Jaclyn even gave ‘normal’ people advice on how to travel. She explained that if you don’t quite have the funds, you shouldn’t rely on the social media profiles of the mega rich and instead, find a location that fits your budget.
Despite making an art out of dealing with billionaires, Jaclyn admitted that growing up, she wasn’t wealthy. 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 feel special. And that’s my expectation for everything I do — I want excellence. It doesn’t always need to be expensive, it just needs to be good. I must’ve been a princess or something in my past life.’
Furthermore, she revealed that when she goes on vacations, she pays for everything herself, instead of getting it comped.
