Who do you call when you want to shut down Versailles for an intimate candlelit dinner? If you’re a billionaire, it’s Jaclyn Sienna India, who founded her members-only travel agency Sienna Charles 16 years ago to serve the whims of ultrawealthy clients. Since then, she has organized multiple parties at the pyramids in Egypt, a private breakfast on the top of the Arc de Triomphe in Paris, and countless million-dollar trips for the world’s Über-rich.
India says that many of her clients don’t even really “live” anywhere — the concept is passé. “Our clients don’t take vacations. Travel is their lifestyle,” she says. Most of them have limitless funds, a desire to spend them, and a vague idea of what they want — but would prefer to outsource the heavy lifting of actually getting it. That’s where she comes in. “We never really have to say no,” India says. “It’s just about how much it costs, and whether you’re willing to pay for it.” Here, she talks about why she’s over hotels (yachts are where it’s at), why her clients always ship their luggage (“Don’t touch your giant Rimowa”), and where the world’s billionaires are going this summer.
How did you get into this business?
When I was 18, I moved to Philadelphia to go to art school at Temple University and got a job at a five-star restaurant called Le Bec-Fin. I worked there for five years and it opened up my whole world. I was enamored with the people who came in — they were dressed beautifully, rolling up in Rolls-Royces and ordering $5,000 bottles of wine. I wanted to study them and understand who they were, why they wanted things a certain way, what made them successful, and what they were doing in their spare time. I wanted to learn about the ingredients the chef flew in, the pheasant from Northern France, what wines we were pairing with it.
When I graduated, I got a job at a travel agency. The trips we did were always fine, but I was struck by the fact that we’d just book flights and a hotel for our clients without thinking about restaurants or other experiences during their trip. Why not customize it more, the way that you would an $8,000 meal at an amazing restaurant? So I created my company 16 years ago based on the ethos of knowing the client, knowing the product, and providing everything they need.
Can you describe your average client?
Many of them have had successful business careers that require them to delegate, so it’s easy for them to delegate in their personal life, too. And they treat their personal life like a business. Which makes sense when they have multiple homes and staff that runs those homes. They have expectations for how they want things to be, whether that’s new flowers every Tuesday or their green tea a certain way. And they want their travel down to a science, too.
Historically, our clients were probably in the age range of 55 to 75. They were in finance, based in New York; that’s still our largest customer base. Then we started getting more clients in Dallas and Los Angeles, with a mix of people in finance and film. Now a lot of our new clients are younger, in the 40-to-50 age range, and they’re in tech.
In the old days, people had personal assistants manage their travel, but now it’s too much for one person to do. People are too wealthy, they’re too busy. Their calendar is a constant flow of what they want to learn about or what they want to do. Let’s say they’re in Palm Beach and someone’s like, “Oh, I’m going to this new members’ club in New York, let’s have dinner there,” so they go the next day. Then, oh, there’s a Rothko exhibit in London, so that’s the next place. People have become really nomadic since COVID.
Why do you think that is? What’s changed?
I think people just have so much money. Honestly, we’ve never seen such massive amounts of money. Whatever you think of — “Oh, I need to get a new dress. I’ll go to New York to go shopping” — there’s no limit. Imagine if you were a billionaire and every time you picked up your phone, there was a new opportunity to shop or buy tickets or go somewhere else, and you could just do it. They’re in L.A. for two weeks because the weather’s nice. And then they’re in Aspen and then they’re at a tech conference at Big Sky, and then they go back to Palm Beach. If you have all the money in the world and you dream of something, you go get it. It’s just about how much it costs, and whether you’re willing to pay for it.
Are clients’ requests getting more over the top?
Nothing surprises me anymore, but everybody’s super last-minute. It’ll be two days before the Super Bowl, and someone’s like, “Do you have Super Bowl tickets?” Sure. “Do you have the best suites available?” Yes. We know that those requests always come in and we plan in advance for that. But people are constantly changing their minds. They’ll give us dates for a trip and we’ll pick the perfect hotel, we’ll pick the perfect suite, we’ll contact the general manager, we’ll get the right flowers in the room, we’ll get the right type of filtered water. Then everything falls to pieces the day before. They’re like, “Oh, I don’t want to go to New York today, I’m still in L.A., the weather’s beautiful.” Everything gets changed. We’ve booked Carbone for them, but then they don’t want to eat at Carbone anymore because they just ate Italian in L.A. and they’re full and they don’t want pasta and they feel fat. So we get rid of pasta and we book salads. It’s hilarious because it’s a moving target that never ends.
How do you hack the dinner-reservation system?
It’s a multilayered process. Restaurants generally fall into three categories. Some have a reservation window that you have to hit. For example, you have to book at the Polo Club 30 days in advance at 10 a.m. Nobu in Malibu, same thing. Then there’s probably ten restaurants in the U.S. that are very hard to get into that have their own protocol — we have to know their system and play by it. Otherwise, you have to know a person at the restaurant and have a relationship with them.
If you can’t make something work, you need great alternatives. When people say, “Oh, I’m going to Napa, I absolutely have to go to the French Laundry,” then I’m like, “Hey, French Laundry hasn’t changed their menu in forever. Why don’t you try SingleThread Farm instead? What they’re doing right now is super exciting.” People want to be guided. They think they want to go to the places that they’ve heard of, but those places are not necessarily the best. They have just been around for a while. When we tell clients about something new, then they get to tell other people about it, and they love that.
How does your business work?
We have two tiers of membership. We charge clients $75,000 a year for unlimited travel and dining reservations. Then it’s $150,000 a year for unlimited travel, unlimited dining, and lifestyle. That would include arranging spa appointments, recruiting house staff, helping clients build a home gym, whatever they need. We find that the first membership is for people who are still quote-unquote “working” — maybe they’re still going to an office regularly. The second one is more for people post-IPO, who have a lot more homes, a lot more lifestyle to manage. Often we work with them in a travel capacity at first, and then eventually they want all hands on deck.
Clients can contact our company anytime through text, WhatsApp, or email. And we become their go-to for anything luxury or luxury-lifestyle related. “How do I hire Taylor Swift for my birthday party?” “Is there a new facial person in L.A. that you like?” There’s no rules other than everything needs to be right now. We acknowledge all emails within five minutes. And all our clients are really nice. We don’t take on any jerks because the amount of work and hand-holding that goes into the back end is really full-on. But to me, there’s no expectation that’s unreasonable. People just want what they want, and they want it now, and our service is built around that — our team is 15 people and we work with fewer than 100 families in total, so everyone gets that one-to-one service.
You still get commissions for your bookings, too, right?
Yes. We get 10 percent from every hotel we book, which is great when you’re booking a lot of $30,000-a-night suites every month. But most of our money comes from the memberships. We’ve had members in the past who paid the $75,000 fee but never even used us. And it’s great to bring that money in, but that’s not the relationship we want. We want people to use us because that’s how we get to know them. We want them to become addicted to us, so they’re signing up year after year. For most of our members, we do around 130 requests a year for them. And if we can’t get them into that restaurant that one day, but we’ve knocked it out of the park for 128 other requests, they keep coming back.
Can you give me some examples of what a client might ask you to do?
I just did a call with a client who’s a tech billionaire. They told me they want to go to Europe in August for nine days, just the couple, no kids. And that’s all they said. This is pretty common. Most of my clients have unlimited money, and they want to spend it, and they have a vision for what they want, but they can’t Google for it. They’re not sure how to find it. They want the guy that’ll open doors for them in Bordeaux so they can taste old wines. They want to go to the most incredible clifftop restaurant in Italy. These are things they can’t find themselves. But I can.
Other times, I’ll get a very specific directive — “We want to take the kids to Rome to learn about gladiators. These are the dates, please arrange it.” Or we get a concept — they want to be on the water in Europe, they want it to be hot and beautiful, but we have to flesh it out.
We’ve closed down Versailles for a private candlelit dinner. We’ve closed down monuments in Turkey. We’ve done really cool parties at the pyramids. We’ve never really had to say no. It all comes down to money. This is the cost. How much do you want to spend? Hospitality is also about being kind and knowing other people in the industry who are open to helping me if I need to get something done.
What do you do when people want something that doesn’t really exist?
A lot of what we do also is managing expectations. For example, a lot of New Yorkers want to go to the Caribbean. And I don’t think that there’s a perfect product there. Every destination has its pros and cons. So we’re honest — for example, here is the most beautiful, perfect beach, but the service isn’t as perfect. I think that’s how you build deep relationships with clients. You know the product and the challenges with it. Then the client feels confident in the trip because they’re aware of what could go wrong.
Were you raised around money and luxury?
Growing up, our family was not wealthy at all. But I was born to be a billionaire, I know it. I was always weird and different. I started working when I was 13 because I wanted my own money. I always wanted things to feel special. And that’s my expectation for everything I do — I want excellence. It doesn’t always need to be expensive, it just needs to be good. I must’ve been a princess or something in my past life.
How do you travel, personally? Do you have to pay for things, or is it all comped?
Sixteen years ago, when I started working in the travel industry, somebody told me how to write an email to a hotel to get free or discounted rooms. It was like, “I’d love to check out your property for my clients. Anything you can do would be greatly appreciated.” I sent that email to the Rosewood Mayakoba and they came back with three free nights. I couldn’t believe it. For the first eight or nine years of my career, I traveled the world for free, flying first-class and staying in the best hotels. Then, in the last five years, the industry changed. There are so many travel agents and so many influencers, and the hotels are at 99 percent occupancy already without our help. So I don’t get anything anymore. And it’s actually better. I’ve learned that paying your own way is a power in itself because there’s no obligation to reciprocate anything. I don’t have to deal with the politics of it.
What are some ways that the ultrawealthy travel that the rest of us wouldn’t know about?
They ship their luggage. Don’t touch your giant Rimowa — just throw a FedEx label on it, and it arrives at your destination the next day. Our clients do it all the time. You don’t have to schlep anything.
Also, there’s less hassle around traveling with pets. I bring my dog everywhere I go. He’s been to 30 countries. You used to be able to get the emotional-support card, but now airlines have made it harder to bring pets onboard. When you travel privately, you just bring the dog on. Companies like VistaJet really celebrate taking care of the pets as well.
Another trend I see is that wealthy people don’t eat out as much as you think. They have their own chefs who travel with them so that they can stay on a diet or keep pace with medical or health goals. We had a client who went to San Francisco for two weeks, and he brought his own chef and only ate out once. He has all the money in the world, but he didn’t want to go to Michelin-star restaurants. A lot of our clients work really, really hard, and it’s important for them to have consistency and routine wherever they go.
Where are the superrich going this summer? Is there a new destination?
Most of my clients have already done the Capri thing, and they’re more interested in unique experiences. They’re taking the yacht around Sardinia or going to smaller islands in Sicily. A lot of extremely wealthy clients aren’t even staying at hotels anymore. I find that many hotels are not conducive to a real ultrahigh-net-worth situation. They have that trophy penthouse, the $30,000-a-night suite, but there’s a lot of heavy lifting to get things the way that the client is used to. People want a certain type of water, or certain foods, or a bedroom that is dark and has seven beds for their dog. When we have to train the hotel staff to do all of that for three days, it’s inefficient. And by the time the staff is trained, then the client is leaving and you’re starting over.
Where do people stay, if not hotels?
Villas and yachts have been a huge part of our business. They are generally owned by a billionaire who has purchased it for his own use. He has customized everything, picked his staff, and trained them for expectations that are otherworldly. And then he’ll open up that experience to others at a very high price. It allows the client to relax deeply because the staff knows how to deliver excellence every minute. It’s an incredible way to travel.
Do you have any advice for “normal” people making travel plans this summer?
You might see a million pictures of celebrities and influencers at the same place, but that doesn’t mean it’ll open up to you in the same way. Like, the Hamptons are good if you stay at somebody’s house and lay out at their pool and you have beach access. But if you go to be a lookie-loo and you’re staying at a hotel and the traffic sucks and you can’t get into a restaurant because nobody knows who you are, then that’s probably not the best destination. There are way better places to go to if you’re on a budget and want to have an authentic experience.
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