Jaclyn Sienna India "The Ghislaine Maxwell of Travel"

The Ultimate Fixer: How Jaclyn built a luxury travel empire from scratch and now curates the world’s most exclusive getaways for presidents, tech billionaires and the elite

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"Vacations are for losers," Jaclyn declares within the first five minutes of our Zoom call.

Bold words coming from a travel advisor.

But I soon discover, Jaclyn Sienna India isn’t just another travel agent—she’s an architect of opulence, crafting ultra-exclusive experiences for the global elite.

"Rich people don’t go on vacation. Travel is just part of their daily existence," she explains.

If anyone knows this world intimately it’s Jaclyn. Raised in modest circumstances, she has navigated her way to the top, becoming the go-to planner for the crème de la crème. Her client list reads like a who’s who of Silicon Valley’s new money millionaires and Palm Beach’s old guard, each trusting her to curate not just trips, but experiences that reflect their stature and sophistication.

But Jaclyn has little patience for what she sees as the diluted portrayal of luxury travel in mainstream media. Despite receiving dream coverage in top-tier magazines—Forbes, Condé Nast, Bloomberg, you name it—she feels the glossy profiles reduce her to just another cliché "girl boss" success story.

"They leave out the real stuff," she says. "Like when I told one journalist that my clients don’t care about carbon emissions—they cut it because it doesn’t fit the environmental agenda they’re pushing." Jaclyn could play along, pretending her billionaire clients care about eco-friendly travel, but that’s not her style.

She’s candid about how her business thrived post-COVID. "The rich have only gotten richer," she notes, a fact often left out of print.

After just ten minutes of unfiltered Jaclyn, I knew I had to introduce her to Jessica.

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Jaclyn invited us to meet her in Los Angeles, where she and her husband Freddy were staying in a mid-century modern Airbnb on Mulholland Drive. We were greeted by the love of her life, Tokyo, her Yorkie, who demands helicopter rides to the airport because he "hates traffic." If Jaclyn can cater to the whims of a bougie Yorkie, it’s no wonder she impresses the world’s wealthiest, who pay her up to $150,000 a year to curate their every moment of their holiday.

She pours us glasses of wine from two brands she swears don’t give you a hangover and we start learning why the CNN comment section called her the “Ghislaine Maxwell of Travel.”

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“I’m a maximalist. I’m not doing- what’s that lady? Marie Kondo? No. I like to bring as much as humanly possible.”

Jaclyn has been to 90 countries, her Rimowa trunk packed tight with a curated selection of supplements, enough to rival an Abbot Kinney wellness shop, and more shoes than even Carrie Bradshaw would pack. Her philosophy? “Bring as much of your shit as possible.” You never know when you’ll need it. She even packs her water distiller so she doesn’t have to rely on fetching bottled waters when she lands at a destination.

Jaclyn starts her mornings with a coffee enema—a must-have in her travel kit—and isn’t shy about showing you a photo of the parasite she expelled at 6 AM. Spending just three hours with her made me rethink my life choices. It’s the Beyoncé effect: realizing you have the same 24 hours in a day, but while you’re doomscrolling eating french fries, she’s planning South American boat trips for her clients on a heavy metal detox.

If you’re fortunate enough to afford Jaclyn’s services, you can reach her through her website, Sienna Charles Luxury Travel and Lifestyle Experiences. But even if you’re not, an hour of her unapologetic banter and unique travel insights on this podcast might be all the inspiration you need to make your next trip a little more special.

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Watch Full Podcast Here (A Must Watch!)

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