20 Minutes With: Luxury Travel Impresario Jaclyn Sienna India

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Jaclyn Sienna
India, founder of
Sienna Charles,
a membership-based travel company, helps wealthy travelers make their most majestic dreams come true, working with clients who typically have a net worth of over US$100 million. She has arranged a private breakfast on the top of the Arc De Triomphe in Paris, brought a yacht to the Galápagos, and arranged backstage passes to meet
Jennifer Lopez
after a concert. 

Sienna India, who founded the first ultra-luxury travel company in 2008, travels 200 days of the year and has visited over 90 countries searching for new experiences for her clients. Her company is based in Los Angeles and limits services to roughly 100 members.

She spoke to Penta about luxury travel trends, sublime travel experiences, and working with billionaires.

PENTA: How is travel changing as people start traveling again?

Jaclyn Sienna India: People are being more careful about where they go, not rushing anywhere. People are also more thoughtful about how they travel and what their goal is. In luxury travel, we’ve noticed the purchase of assets, rather than renting them. A lot of clients started buying vacation homes where we were sending them, as well as yachts and chartered planes. People are not sharing their trips on social media. Privacy is important.

Who are your clients?

Most of our clients work in finance. We work with presidents of countries and celebrities—privacy is at the core of what we do, so we don’t name names. They usually live in New York, Los Angeles, and Palm Beach, they usually travel with their family. We assist with travel and lifestyle services, including wellness, we help them with real estate needs, build yachts, anything luxury lifestyle related.

How does membership work?

We charge between US$75,000 and up annually for access to me and my team. We help them plan unlimited lifestyle luxury experiences, travel, or related. We started in 2008 as a travel agency striving to be more. We realized the nuances that go towards designing a trip became an intimate experience; understanding who they are and what they love—it was really about pursuing their passions, be it food or history.

What kind of information do you collect on your trips?

I source the best restaurants, experiences, and chefs. I amassed this black book of people, places, and things, on top of my own passions, wellness, and art. It made me open that black book to anything. I would get a ping: “Where should I get a massage in L.A.?” or “Who is the best acupuncturist?” I felt people were coming to me for my take on luxury lifestyle. I’m constantly scouring for the best of everyone and everything.

What goes into your research?

When they come to me and they sign up, not everything has to be a ‘wow’ moment, but it has to be right. If they get there and love the experience, great. But they already had a vision of what they expected but couldn’t make it happen because they don’t know the world like I do. It’s a unique service perfectly tailored to them. Money is no object, so we can get creative.

What are currently the most popular kind of experience for wealthy individuals?

[Yachting] is the most popular it has been. They sometimes pay US$100,00 to US$300,000 a week for a boat and bring their multi-generational family for a trip. It’s quite busy overall. This summer, we did the Bahamas, Croatia, Italy, and France. 

Private aviation is huge right now. A lot of people who flew commercial will only fly private now. It’s about quality and service for us. People aren’t willing to compromise on quality, which fits into exactly what we do.

Has being around so many CEOs who are experts in leadership helped your own business grow? Has some of their wisdom rubbed off on you?

A hundred percent, that’s what got me into the business. I was working at a five-star restaurant when I was in college and the people who came in were the wealthiest people in the city. I didn’t come from that background, but I admired their success and wanted to learn everything about them to model my own life after it. 

Whether it’s the way I run my business, my level of efficiency or the way I communicate. Or the standards I hold myself to. I continue to be in awe of that—having lunch with my billionaire clients, which I do a few times a week. It gives me the chance to understand who they are, what makes them successful, and what makes them tick. It’s so valuable and I’m lucky to be able to do that.

This interview has been edited for length and clarity.