From Skepticism to Success: The Journey of a Luxury Travel Maven

In 2008, Jaclyn Sienna India founded Sienna Charles, a boutique travel concierge service, with the mindset of “fake it until you make it.” Initially, she faced skepticism, even from her husband, as she fielded inquiries from people interested in travel arrangements that she was not yet able to provide. “I was like, ‘Oh, I’m sorry, we’re so busy, we’re really sold out this season with high-net-worth people,’” India recalled, despite having no clients at the time.

Fast forward sixteen years, and her strategy has proven successful. India now serves a prestigious clientele, including former President George W. Bush and celebrities like Mariah Carey, focusing on individuals with annual earnings exceeding $100 million. Her services go beyond what wealthy clients can achieve on their own, emphasizing personal care and attention.

India attributes her success to her background as a server for five years, where she learned the importance of understanding people’s needs. “It’s care. It’s leading from the heart,” she stated, highlighting the value of genuine relationships.

Sienna Charles boasts an extensive network of over 2,000 contacts within the hospitality sector, which enables India to curate unique travel and dining experiences for her clients. “They just don’t have the tools, the time, the access, and the creativity to be able to fulfill that,” she explained about her clients. Her strength lies in capturing their vision and bringing it to fruition.

India focuses not just on providing access to glamorous venues, but also on ensuring that experiences are meaningful. For example, she does not promote the renowned French Laundry restaurant, believing that alternatives like Single Thread Farms offer more exciting options.

Her unique offerings include special events, such as candlelight dinners at Versailles and brunch atop the Arc de Triomphe, often paired with meetings with influential personalities, like breakfasts with the Hermes family.

Sometimes her clients’ requests are more straightforward. For a trip to Ethiopia, she made sure former President Bush had a taste of home with peanut butter and non-alcoholic beer, and he was welcomed by children wearing Texas Rangers baseball caps.

India expresses a deep commitment to her clients, spending her time engaging with various people, from cab drivers to restaurant staff, to discover authentic experiences beyond mere luxury. “The world is not just fancy experiences. It’s everything,” she said, emphasizing her dedication to providing genuine, memorable moments.

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