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4 travel secrets of the mega-rich, from a vacation planner for billionaires

In Business
April 20, 2024

Imagine closing down Versailles to enjoy a private candlelit dinner.

That’s the reality for the ultra rich, and people like Jaclyn Sienna India make it happen.

India is the founder of a Sienna Charles, a members-only travel agency that caters to wealthy clients who take million-dollar trips around the world. India recently discussed her work and billionaire clientele in a Q&A with The Cut.

Her company’s services include a $75,000 annual tier for unlimited travel and dining reservations, and a $150,000 yearly option to tack on a “lifestyle” component. That includes “arranging spa appointments, recruiting house staff, helping clients build a home gym, whatever they need,” India told The Cut.

She shared some of the travel secrets of her unthinkably wealthy clients:

1. Penthouse suites are out, yachts are in

Most of India’s clients are 55- to 75-year-old ex-finance workers in New York City, but in recent years, she’s seen more interest from people in Dallas and Los Angeles who work in finance or film. Her newest clientele are tech VIPs in their 40s and 50s.

India’s typical clients are no stranger to booking hotel suites for $30,000 a night, but it’s becoming more passe.

The mega-rich want their accommodations loaded up with their preferred foods, fancy water and drinks as well as other, more-specific requests (a space with seven dog beds, for instance), but training hotel staff on everything within a few days is inefficient.

The trendier thing to do is stay at a villa or yacht owned and rented out by billionaires.

“[The owner] has customized everything, picked his staff, and trained them for expectations that are otherworldly,” India said. All of that means her clients can “relax deeply because the staff knows how to deliver excellence every minute.”

2. They don’t deal with luggage

Unlike the rest of us, the rich aren’t worried about airline baggage fees. Then again, they’re not schlepping their suitcases at all.

Instead, they ship it, India said: “Just throw a FedEx label on it, and it arrives at your destination the next day.”

3. They’re not dining out at fancy restaurants

Though Sienna Charles staffers know all the best restaurants and how to get impossible reservations, India says many of her clients don’t eat out when they travel.

That’s what their private chefs are for, she says.

The chefs travel with clients and help maintain their diet and medical or health goals, India said. She gave an example of one client who traveled to San Francisco for two weeks, brought his chef and only ate out once.

“He has all the money in the world, but he didn’t want to go to Michelin-star restaurants,” India told The Cut. “A lot of our clients work really, really hard, and it’s important for them to have consistency and routine wherever they go.”

4. They want unique experiences

If you want to rub shoulders with a billionaire this summer, India said they’re increasingly trading the typical hotspots (think: Capri) for more “unique experiences.”

“They’re taking the yacht around Sardinia or going to smaller islands in Sicily,” she said.

Sometimes her clients have specific travel requests, like wanting to take a family trip to Rome in a specific timeframe. More often than not, they’re pretty general about their vision and want help with the specific details.

One recent tech billionaire “told me they want to go to Europe in August for nine days, just the couple, no kids,” India said. “And that’s all they said. This is pretty common.”

As for those with more modest means, India’s best advice is to “normal” people is to steer away from places where celebrities and influencers abound. Or, at least, recognize that you’re unlikely to get a similar A-lister experience if you go.

For example, she said, “The Hamptons are good if you stay at somebody’s house and lay out at their pool and you have beach access. But if you go to be a lookie-loo and you’re staying at a hotel and the traffic sucks and you can’t get into a restaurant because nobody knows who you are, then that’s probably not the best destination.”

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