From Faking It to Five-Star: The Rise of a Luxury Travel Maven

When Jaclyn Sienna India launched Sienna Charles, her travel concierge service, in 2008, she adopted a “fake it till you make it” approach. Despite her husband’s skepticism about her business, which had no clients at the time, India managed to project an image of success. She frequently received inquiries from potential clients seeking travel opportunities, which she would politely decline, claiming to be fully booked with high-profile patrons.

Fast forward 16 years, and India’s strategy has proven fruitful. She now caters to a roster of clients, including prominent figures such as former President George W. Bush and celebrities like Mariah Carey. Her services are tailored for individuals with an annual income exceeding $100 million, clients who seem to have it all. So, what unique value does India offer them?

India notes that her clients are influential and well-connected, yet she believes that true success in fulfilling their needs comes from genuine care. Drawing from her experience as a server, she emphasizes the importance of understanding and prioritizing clients’ desires.

Sienna Charles boasts an extensive network, often referred to as her “black book,” containing over 2,000 relationships within the luxury hospitality sector, including connections with yachts, high-end hotels, and exclusive restaurants. This network allows her to curate exceptional travel and dining experiences tailored to her clients’ aspirations.

“My clients are articulate about what they want to achieve, but they often lack the resources and creativity to bring those visions to life,” India explains. She considers it her gift to grasp their aspirations and deliver on them effectively.

However, India’s mission extends beyond securing reservations at the most luxurious venues; she is also committed to ensuring that the experiences are meaningful. For instance, she does not promote popular locations like the French Laundry in Napa, as she believes there are more exciting alternatives, such as Single Thread Farms.

India focuses on crafting unique and personalized experiences for her clients. She recalls arranging a romantic candlelight dinner in Versailles and brunch on the Arc de Triomphe. Additionally, she facilitates opportunities for her clients to meet influential figures, organizing breakfast meetings with the Hermes family and lunches with the Fendi family in Rome.

Sometimes, her clients prefer simpler comforts. When arranging for Bush’s visit to Ethiopia, India made sure he had familiar items like peanut butter and non-alcoholic beer, alongside a warm welcome from local children wearing Texas Rangers baseball caps.

“I truly care about people,” she shares. India dedicates her days to connecting with various individuals, from cab drivers to restaurant staff, in search of authentic experiences for her clients. She believes that the world encompasses more than just luxury; it is about offering genuine and meaningful experiences.

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