Sienna Charles: Luxury travel agent plans trips for former US presidents and world leaders

(CNN) — On a personal trip to Ethiopia in 2015, former US President George W. Bush encountered a pleasant surprise.

When he arrived in the ancient Christian town of Lalibela, dozens of children wearing royal blue Texas Ranger hats — one of the Texan’s favorite sports teams — gave him a warm welcome.

“I try to think of cool ways to make (travelers) excited, so I bought about 100 Texas Rangers hats. And when Bush came to the village, all the kids had them on.”

Personal touches, exclusivity, security, discretion — these are the things that world leaders have come to expect while traveling.

“It’s very much like theater — world leaders have this vision of what this place could be like, how exotic and how amazing,” adds India. “And we want to fulfill that vision with special moments.”

Bush was not the first world leader India worked with. Her agency has planned more than 100 journeys for at least 15 presidents, prime ministers and premiers since 2012.

“Whether it’s a former president or billionaire or celebrity, everybody’s an individual,” she says.

“If you understand what makes them tick and why are they taking that trip, it will be a successful relationship.”

In 2015, luxury travel specialist Jaclyn Sienna India accompanied former president George W. Bush to Ethiopia's Omo Valley.

In 2015, luxury travel specialist Jaclyn Sienna India accompanied former president George W. Bush to Ethiopia’s Omo Valley.

Courtesy Sienna Charles

Delivering tailored experiences

India learned all about the art of luxury hospitality at now closed Le Bec Fin, at the time a fine dining restaurant with three Michelin stars, where she worked while earning a bachelor’s degree in art history at the Tyler School of Art at Philadelphia’s Temple University.

“I fell in love with servicing the ultra-high-net-worth,” she recalls. “I really excelled and understood their needs. That’s really been the success of my career — understanding the needs of each person and then being able to deliver that experience.”

After college, the New York native moved to Palm Beach, Florida, with her then boyfriend and now husband, Freddy Charles Reinert, where she quickly realized the level of service in “luxury” tourism paled by comparison.

Sienna Charles has even managed to gain its clients private access to the Louvre.

Sienna Charles has even managed to gain its clients private access to the Louvre.

Frédéric Soltan/Corbis/Getty Images

“It just didn’t make sense to me; at the restaurant, you would sit down for three hours and spend $5,000-10,000,” she recalls.

“You’d have seven people waiting on you with silver (tableware); the somm knew every grape and winemaker; the chef came out to your table and knew where the foie gras came from.”

Everything was obsessive and service-driven at the restaurant, she says, but that was not so in luxury travel.

“The same type of clientele would be spending $100,000 on a trip to Italy or France but the (travel agent designing) the trip had never even been there,” says India.

Striving to offer a better alternative for high-net-worth travelers, the pair launched Sienna Charles in 2008.

Every trip is tailored to the client’s needs, be that a multi-generational retreat in Umbria or a private island in Indonesia.

“I personally vet all of my recommendations and am obsessed with quality and service,” she says.

An adventure through Egypt

In 2012, Sienna Charles had a chance to plan and execute a trip for a world leader for the first time.

When approaching India, the client (whose name cannot be shared due to a non-disclosure agreement), had their sights set on Egypt.

The leader had previously visited the country for work and was “really interested in Egyptology,” says India.

"We closed down monuments for (the leader), and they just wanted to dig deeper into their personal passion," recalls India of a trip to Luxor, Egypt she planned in 2012.

“We closed down monuments for (the leader), and they just wanted to dig deeper into their personal passion,” recalls India of a trip to Luxor, Egypt she planned in 2012.

Khaled Desouki/AFP/Getty Images

So the travel expert arranged a multi-stop, 12-day adventure that peppered in history and cultural discussions with several professionals and academics.

The trip took the world leader from Cairo to a Nile cruise on a private yacht, with several stops at historic sites along the way.

They finished the journey in the ancient capital of Luxor — nicknamed the “world’s greatest open-air museum” — where some of the country’s oldest tombs and temples can be found.

“We closed down monuments for (the leader), and they just wanted to dig deeper into their personal passion,” recalls India. “They had this romantic sense of the world where they just couldn’t wait to discover this place.”

Thanks to referrals and this first successful trip with a world leader, India went on to plan trips for George W. Bush, among several other world leaders.

The Bushes in Ethiopia

In 2015, India meticulously choreographed a trip to some of the most remote corners of Ethiopia for Bush, his wife Laura, four friends, his doctor and 30 Secret Service staff.

Due to the massive entourage, word got out about the trip.

“We’re all about discretion and privacy,” says India. “But with so many staff and Secret Service agents, it just became a media frenzy. Some world leaders just go with one security agent and a baseball cap — and nobody knows that it’s them.”

Lalibela, Ethiopia is famed for its gorgeous rock-hewn churches.

Lalibela, Ethiopia is famed for its gorgeous rock-hewn churches.

Edwin Remsberg/VWPics/Universal Images Group/Getty Images

She says Bush chose Ethiopia because he had been there during his presidency but didn’t have enough time to get out and explore in more depth.

“He told me that he visited about 80 countries during his presidency, but would be at a beautiful monument like the Taj (Mahal) and never really see anything (due to the demanding schedule),” adds India.

To immerse the former president in culture and history, she planned a multi-leg journey from the remote Omo River Valley — home to some of the world’s most isolated tribes — in the south up to Lalibela in the north.

The logistically challenging trip required various modes of transport, from SUVs to helicopters, private jets and riverboats.

“Lalibela is all about Christianity — that was amazing,” says India, alluding to Bush’s religious affiliation. “When we were in the Omo Valley, (villagers) did a ceremonial dance to welcome him.”

All about the personal touches

India’s team catered to highly specific requests for food and drink, since “the trip is all about them.”

For example, she says Bush likes comfort foods like peanut butter sandwiches and pasta when he travels, so India ensured all of his favorite meals were available even in the most remote parts of Ethiopia.

“For world leaders, service is at a level of insanity in their homes and they have executive assistants everywhere they go,” she explains. “So when they travel, they really have high expectations — and understandably so.”

"When you're willing to pay, it's a really easy conversation," says India of how Sienna Charles managed to close down major world monuments for clients, including the Hagia Sophia in Istanbul, pictured.

“When you’re willing to pay, it’s a really easy conversation,” says India of how Sienna Charles managed to close down major world monuments for clients, including the Hagia Sophia in Istanbul, pictured.

Yunus Emre Gunaydin/Anadolu Agency/Getty Images

Since the hotels in Ethiopia did not meet India’s expectations, she worked with local partners to build luxury camps for the former president and his entourage instead.

They purchased brand new furniture, bedding, sheets — building beautiful accommodations from scratch.

The nice thing about working with world leaders, she says, is that they know how to delegate.

“I tell them what we’re thinking and they let me run with it. These are people who run countries, so they understand the power of hiring experts and can relinquish (control) to people who are good at what they do,” says India.

Once, she helped a world leader celebrate his wife’s birthday by covering the entire floor of a private villa with exotic “Cherry Snow” roses flown in from Ecuador, she says.

Another time, she worked with movie set producers and styling experts to create a cinematic Parisian scene in the heart of Miami, where famed chef Eric Ripert designed a special menu.

And in Italy, she arranged for a world leader to enjoy a private visit with a famous jewelry designer. The leader helped design a unique gift for his wife — a gold Navette ring with an oval-cut faceted ruby and 24 round-cut diamonds for $714,000.

Discretion, security and exclusivity

In most cases, India says her clients come to her with a vision of what they hope to experience on a trip.

Perhaps that’s taking a deeper dive into Chinese culture, lazing by the pool in St. Barts, or simply renting a house and being a grandpa for a week in Italy.

After an initial consultation, India — who has traveled to more than 80 countries and insists on experiencing each recommendation first-hand — will typically suggest three to five options, outlining the pros and cons of each.

From there, the travel expert works closely with the client’s chief of staff, personal assistant and security to iron out the details.

“From the room type to food allergies, what type of restaurants they like, what time they like to wake up, what newspapers they want in the room, what type of tour guides they like … we take every detail into account,” she says.

India has taken clients on exclusive, private tours of Machu Picchu.

India has taken clients on exclusive, private tours of Machu Picchu.

Pablo Porciuncula Brune/AFP/Getty Images

Transport tends to be relatively smooth since 100% of her clients have their own private yachts, helicopters and private jets.

As part of security protocol, Sienna Charles often needs to close down major monuments and museums so clients can experience them alone.

“We’ve closed down the Sydney Opera House, the Hagia Sophia in Istanbul, the Louvre, Versailles, the Great Sphinx of Giza, Machu Picchu… tons of monuments,” says India. “When you’re willing to pay, it’s a really easy conversation.”

Typically, Sienna Charles first tries to arrange a visit during off-hours. If that’s not possible, they attempt to make a donation of anywhere from $20,000 to $100,000.

“We don’t need to spend money just for the sake of spending money,” she says. “You just have to know who to call. But if they’re able to view it in a private manner, that’s a win.”

Leaving room for spontaneity

Security is much more challenging, especially when working with world leaders who tend to travel with at least one security agent.

“They have a lot of security — and the security wants an itinerary,” she says. “They want it mapped out from literally how many steps we have to take from the car to every monument to every restaurant.”

Initially, this was quite frustrating for India because she believes that “travel is all about being serendipitous.”

“The trip unfolds as (our clients) are traveling. We learned pretty quickly after that first trip (in Egypt) that yes, we’ll prepare a minute by minute account of what we’re going to do for the security teams, but we also have to manage the client,” she says. “And if the client feels like it’s a great trip, that’s a win for me.”

That means, at times, venturing off the minute-by-minute itinerary. For example, when she took Bush to Ethiopia, India had an unexpected opportunity to visit a remote tribe in the Omo River Valley.

But the group would have to shimmy down a very steep path with poor visibility to reach the river, then take a boat to get there.

“I asked his staff if he could do it so (Bush) could see more. And they said absolutely not,” recalls India.

“But this would be the only way we would get a moment with this tribe, so I asked Bush directly, and he said, ‘Absolutely.'”

“I’ve learned to respect the security and staff who want to keep the person safe, but that (strict itinerary) can also shield them from enjoying things,” she says.

A new era for ‘out of control’ spending

The pandemic hasn’t impacted the travels of the ultra-wealthy and elites, says India.

“There are a lot of places like Fiji and Thailand that started letting private jets in about six months ago,” she says. “It’s an advantageous time to be an ultra-high-net-worth person. Because, like anything else, money talks. People are willing to spend the money to do whatever they want.”

She has noticed several ultra-luxury travel trends spurred by the pandemic. For instance, India’s clients tend to plan trips at the last minute — sometimes just a day or two in advance — due to the uncertainty of border restrictions and quarantine requirements.

They have also started skipping intermediaries entirely, purchasing their own yachts and private jets and buying vacation homes.

What’s more, India says discretion has become the norm.

Gardens of the 'Orangerie' of Versailles Palace.

Gardens of the ‘Orangerie’ of Versailles Palace.

Stephane De Sakutin/AFP/Getty Images

“They are not traveling just for the sake of travel. But when they do go, the wealthy are not sharing online anymore,” she says. “When so much of the world is struggling, they’re not going to post photos aboard their mega yacht.”

Still, the money spent on trips right now is “insane”, she adds. “People just want what they want. If they are chartering, it’s going to be the most expensive yacht. And they’re not messing around with staff who don’t know how to deal with them.”

Before the pandemic, India would help clients charter yachts for roughly $200,000 to $300,000 a week. Now, they are booking boats that cost up to $1 million a week.

When it comes to vacation homes and estates, spending has skyrocketed from an average of $10,000 a night to $35,000 or more for Sienna Charles clients.

“The spending is certainly out of control,” says India. “It’s across the board. People are just willing to pay for exclusivity and being at the right place at the right time. Always.”

Top image: Jaclyn Sienna India, founder of the Sienna Charles luxury lifestyle company. Credit: Anna Gunselman

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