From Faking It to Exclusive Travel: The Rise of Jaclyn Sienna India

When Jaclyn Sienna India launched Sienna Charles, her boutique travel concierge service, in 2008, she was committed to the philosophy of “fake it until you make it.” Initially, she found herself in a challenging position where potential clients would reach out, but she had no existing clientele to back her claims. She would often tell callers that her services were fully booked with high-net-worth individuals, despite the fact that she had no clients at the time.

Fast forward sixteen years, and her strategy has paid off. India now counts several prominent figures among her clients, including former President George W. Bush and iconic celebrities like Mariah Carey. Her specialized services cater to individuals earning over $100 million annually, focusing on clients who may have everything but seek extraordinary experiences.

India emphasizes that her value lies not in her connections but in her genuine care and understanding of her clients. Drawing from her background as a server for five years, she has honed the ability to empathize with people and prioritize their needs.

Sienna Charles maintains an extensive “black book” that includes over 2,000 industry connections across luxury hospitality, offering exclusive access to yachts, hotels, and high-end dining. This capability enables India to curate bespoke travel and culinary experiences tailored to her clients’ visions.

Her approach transcends simply providing access to elite venues. India believes that authenticity is key, often recommending experiences she finds more meaningful or engaging. For instance, she prioritizes unique dining experiences, like recommending Single Thread Farms instead of the well-known French Laundry.

India’s service includes crafting unforgettable moments; she once arranged a candlelight dinner in Versailles and a brunch on the Arc de Triomphe. She also seeks to connect her clients with notable personalities, organizing meals with families like Hermes and Fendi.

Despite her high-profile clientele, sometimes the needs are more straightforward. For Bush’s trip to Ethiopia, she made sure he had his favorite comforts—peanut butter and non-alcoholic beer—while also arranging for local children to greet him wearing Texas Rangers caps.

India’s approach centers on understanding that luxury isn’t always about opulence; it’s about providing authentic experiences. She maintains a hands-on approach, engaging with everyone from cab drivers to restaurant staff to discover unique opportunities for her clients. Her commitment to genuine care and exceptional service continues to set her apart in the competitive luxury travel market.

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