April 13, 2024


Booking Travel

I’m a Travel Agent Who Plans Luxury Vacations for Billionaires and Celebrities

This as-told-to essay is based on a conversation with Jaclyn Sienna India, the founder of the luxury travel concierge Sienna Charles. The following has been edited for length and clarity.

I attended university for art history. I was a typical college kid, but at that time, I started working at a five-star French luxury restaurant, Le Bec-Fin, as a server. I didn’t know how much that restaurant would impact my life.

The clients coming in came from wealthy backgrounds. I saw people spend $10,000 on dinner. They were super dressed up, covered in jewels, and coming in with Rolls-Royces to dine on the best food and drink the best wine.

I became enamored with studying people with ultra-high net worths. I wanted to take that elegance, knowledge, and personal service I learned in the restaurant and bring it to travel.

Faking it until I made it

I started my own travel concierge, Sienna Charles, 16 years ago. I definitely faked it until I made it, but I believed in it.

You could start a business for $99. But what you do with that after is when you start to grow as an entrepreneur. I opened my business, but it’s not like the phone rang.

At that time, I was writing to Gotham Magazine and Manhattan Magazine, telling them that I was the most exclusive travel company in the world.

My husband thought I was the dumbest person in the world because we would get calls from people saying, “Oh, I saw your article. I’d love to go to Disney,” or, “We’re going to New Jersey for the weekend.” And I was like, “Oh, I’m sorry, we’re so busy, we’re really sold out this season with high-net-worth people.”

But I had no clients. My husband would say, “You’re an idiot. Take the trip.” And my response was, “No. I either work for the wealthy or I don’t.”

Jaclyn and her husband.

Jaclyn Sienna India and her husband.

Courtesy of Sienna Charles

It took me three years to get a client. After booking my first billionaire client, I put the $30,000 profit toward my personal travel.

Most people would think I was an idiot at that time because I didn’t have the money. In retrospect, it was about understanding the product.

I took it just as seriously from the beginning as I do today.

My dream was to create, for lack of a better term, a one-stop shop because the industry was so segmented. If you wanted to go on an African safari, you would call Abercrombie and Kent. If you wanted to go to Paris, you would call this person. You would call a broker if you wanted to go on a yacht. If you wanted to get a plane, you would call somebody else.

I wanted to be that one point of contact all the time for that wealthy person.

My clients are billionaires and A-listers with type-A personalities

Clients typically come to us. Their average net worth generally starts at $100 million. Annual membership fees range between $75,000 and $150,000, depending on the services clients require. On the lower end, that includes travel and dining services at home and while traveling. The higher-paying members get access to that plus lifestyle services.

But all members get access to our team 24/7 and my personal black book. We work with less than 100 families. We’re handling their dining while they’re at their multiple homes and booking their trips. We’re an extension of them and their team.

When they reach out and want to become a member, there’s an interview and then an onboarding preference call where we get to know them and build out their profile. We ask questions like: What are you comfortable spending nightly at a hotel? Do you prefer contemporary hotels or a more classical style? What are your favorite dining times? Are you OK with tasting menus? What type of guide do you like? We collect all that, and then as the travel and lifestyle requests come in, we use those preferences to help clients with anything and everything throughout the year.

We’re learning about them constantly and using information to improve every experience. Some people want calendar invites, others want the mobile app, and others only want to email.

It’s a very difficult, complex business because it’s not one size fits all.

During COVID, we helped people gain second passports and pick new locations to build a home. We’re first and foremost a travel company, but because we have such a great methodology of sourcing like-minded vendors that share our ethos, we’re often asked to help clients with different aspects of their lifestyles.

George W. Bush and Jaclyn Sienna Charles in Ethiopia.

George W. Bush and Jaclyn Sienna India in Ethiopia.

Courtesy of Sienna Charles

Many of the people we handle are A-list celebrities, but also very much the billionaire next door. They are generally self-made entrepreneurs and CEOs, and they have type-A personalities.

The expectations are quite high. But I’ve learned if somebody’s willing to give $75,000, it doesn’t mean they’re a fit.

We’ve had people who don’t want to relinquish control. That doesn’t work. We need to be on the same page.

But it generally works out well. When you have a CEO, whether male or female, they understand the principles of a successful relationship as communication, delegation, and hiring somebody to handle a problem you’re looking to solve.

I have a unique relationship with our members. They’re the smartest, busiest, most incredible, talented people in the world. It’s a family. The fact that they trust us is not taken with a grain of salt.

We do sign an NDA with clients now. Ones not covered by an NDA are George W. Bush and Mariah Carey.

And we’ve done it all. Money talks, right? If you want to close down the Taj Mahal or you want to close down monuments in Turkey, we’ve gotten it done. People just want what they want and are willing to pay for it.

I specialize in quiet luxury travel

In terms of the trips, we do the simple to the sublime.

Clients could live in Los Angeles and not have an apartment in New York City and maybe want to go there for three nights and stay at a great hotel — that trip could be $10,000 a night in a hotel. So, we do those regular trips and trips that cost well into the millions, like going to Africa with helicopters and private jets.

Before it had a name, we definitely had been practicing quiet luxury travel and hospitality.

Almost all the clients we have don’t want to be seen. They’ve reached a level in their success where they don’t need to prove it to people by taking pictures of their pasta at Carbone.

The people in Capri in July are one set of people, and the people on a small island on their own yacht in Sicily are another group. That’s the people we cater to.

Sienna Charles specializes in "quiet luxury" travel.

Sienna Charles specializes in “quiet luxury” travel.

mr-fox/Getty Images

You can read 1,000 travel magazines, and people say, “This new hotel is incredible.” I don’t think it’s incredible until I go there and see what I think of it.

So many times, I’d been excited about a popular new hotel or destination and was disappointed.

However, the beauty of hospitality projects, whether a hotel or restaurant, is that they always have an opportunity to improve because they learn from their mistakes.

But being on a list just means that everyone who follows lists will go there. I’ve become a real filter for our members to ensure they only visit phenomenal places that live up to expectations.

I rarely travel for leisure

I’ll take a vacation very rarely. It’ll be when I know everything is all set, like after Christmas to January 15th, when everybody’s on mental break.

Everything else is work. Every week, I’m generally in two places.

I’m on the computer answering the team all day and night. I work 40 to 50 hours, sometimes 60 hours a week. When I travel in Europe, before the team gets on, my calendar is filled with site inspections, meetings with clients, or meetings with new vendors.

Jaclyn Sienna India says she has a type-A personality, like most of her clients.

Jaclyn Sienna India says she has a type-A personality, like most of her clients.

Courtesy of Sienna Charles

I have a very type-A personality. I’m focused on living and breathing by my calendar and having every minute dedicated to the company’s growth.

I use my own service. I don’t think many owners try their own service or know how everything flows.

We often get asked to sell our company. I don’t want to sell my company; I’m still learning. It’s something that drives me every day.

It’s like polishing a diamond. Every day, I become a better business person and a better leader to handle the challenges of running a 20-person team that is committing to the most difficult people in the world, in the most difficult time in history, to deliver phenomenal customer service every minute of the day.