From ‘Fake It’ to Fabulous: The Rise of a Luxury Travel Guru

Jaclyn Sienna India launched Sienna Charles, her boutique travel concierge service, in 2008 with a determination to “fake it until you make it.” Initially, she faced skepticism, including from her husband, as she handled calls from prospective clients seeking travel bookings. Without any clients, she would tell them that her service was fully booked with high-net-worth individuals.

Fast forward sixteen years, and her strategy has proven successful. India now counts former President George W. Bush and celebrity Mariah Carey among her clients, catering specifically to individuals with annual incomes exceeding $100 million. The question arises: what unique offerings does India provide that her affluent clients cannot secure themselves?

India believes that personal care and empathy set her apart. Drawing from her previous experience as a server, she emphasizes the importance of understanding the needs and desires of her clients. Sienna Charles maintains a comprehensive network, boasting over 2,000 contacts in the hospitality sector, which enables India to craft extraordinary travel and dining experiences for her clientele.

She notes, “My clients express their visions to me. They see what they want but lack the time, access, and creativity to realize it. One of my strengths is translating their ideas into reality.” However, India’s goal transcends merely securing exclusive venue access; she aims to deliver enriching and memorable experiences.

For instance, she provocatively mentioned that she doesn’t promote dining at the well-known French Laundry restaurant, as she finds other venues, like Single Thread Farms, to be more exciting. Her services often include exclusive and unique events, such as a candlelight dinner at Versailles or brunch on the Arc de Triomphe. Moreover, India has arranged meals with influential figures, including a breakfast with the Hermes family and lunch with the Fendi family in Rome.

At times, her clients prefer simpler comforts. When arranging a trip for Bush to Ethiopia, she made sure he had familiar snacks, like peanut butter and non-alcoholic beer, and arranged for him to be welcomed by children in Texas Rangers baseball caps.

“My genuine care for people drives my work,” India explains. She dedicates her day to connecting with various individuals, including cab drivers and restaurant staff, to uncover unique opportunities for her clients. Ultimately, her focus is on delivering authentic experiences that reflect the diversity of the world, rather than just luxury.

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