From Skepticism to Stardom: How Jaclyn Sienna India Redefined Luxury Travel

Jaclyn Sienna India founded Sienna Charles, a boutique travel concierge, in 2008 with the mindset of “fake it until you make it.” Initially, she faced skepticism, even from her husband, as she received inquiries from potential clients despite not having any actual clients at the time. She would tell them that her services were fully booked, even though she was just starting out.

Fast forward sixteen years, and India’s strategy has paid off significantly. She now serves high-profile clients including world leaders like former President George W. Bush and celebrities such as Mariah Carey. Her clientele comprises individuals who earn over $100 million annually, a demographic that seemingly has access to everything. So, what unique offerings does India provide?

India emphasizes the importance of empathy and personal connections. Drawing on her five years of experience as a server, she believes understanding what drives people is crucial. Her attention to detail and genuine care for her clients set her apart in the industry.

Sienna Charles maintains a vast network, boasting over 2,000 industry contacts across the hospitality sector, including luxury hotels, yachts, and fine dining establishments. This extensive relationship-building allows India to create exclusive travel and dining experiences tailored to her clients’ desires.

She highlights a unique aspect of her service—understanding a client’s vision through mere hints and delivering it precisely. However, her mission transcends simply getting clients into exclusive venues; she aims for the experiences to hold real significance. For instance, she noted her lack of enthusiasm for dining at upscale locations like French Laundry because she believes other options, such as Single Thread Farms, offer more memorable experiences.

India often arranges extraordinary events for her clients, such as a candlelit dinner in Versailles or brunch on the Arc de Triomphe. Additionally, she integrates encounters with notable figures into dining experiences, having arranged meals with the Hermes and Fendi families.

Sometimes, her clients seek simple comforts. When Bush visited Ethiopia, she made sure he had peanut butter and non-alcoholic beer, along with a warm welcome from local children wearing Texas Rangers baseball caps.

At the core of India’s approach is a deep care for people. She engages with everyone from cab drivers to restaurant staff to uncover the most interesting options for her clients. For her, true luxury is not solely about extravagant experiences; it’s about authenticity and genuine connections.

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