The business of six figure+ travel

With Erina Pindar, COO of SmartFlyer

Hello everyone, happy Thursday.

This edition of The Stanza’s “In The Room” column is a special one, as I’m introducing one of The Stanza’s 2026 partners: SmartFlyer. A few weeks ago, I shared my notes from their internal conference about the business of high-end travel and what it takes to sell those outrageously priced hotel rooms. A hotelier behind one of Italy’s objectively best hotels told me that SmartFlyer is consistently a top 3 source of business for peer hotels across Italy. Their numbers share some more insight into how big the luxury travel advisory business is: in 2025, SmartFlyer booked $1.02B in travel across its 250 agencies.

Erina Pindar is the COO and Managing Partner of SmartFlyer, a luxury travel advisory founded in 1990 by Michael Holtz. SmartFlyer originally started as an air travel agency business, but has since grown into a 360 luxury travel platform guided by the principle that travel has the power to positively transform the human experience.

As The Stanza evolves to explore the various facets of the hospitality business, I’m excited to introduce SmartFlyer as an aligned partner. As always, if you have any questions about the high-end travel advisory business, you’re welcome to directly reply to this email.

Hotel du Cap is one of SmartFlyer’s most booked hotels.

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What aspects of hospitality shape how you approach the travel advisory business?

Travel is such a human endeavor. You’re working with people as clients, as partners, and of course, as advisors. Hospitality is this world where everyone is always rushing to open the doors for each other, and that’s what I’ve always loved about it. Learning how to understand and anticipate what people need — sometimes before they even ask for it — has been the biggest influence in how I choose to lead.

Of course there are concrete things about building a business, but the EQ side of leadership is really the most important, especially in hospitality.

In the past couple years, luxury hospitality has exploded. And with that, different segments of “luxury” have emerged: ultra-luxury, aspirational luxury, etc. Where do you see the line between luxury and value in today’s world? And has that definition changed since you started?

My definition of luxury has always been that luxury is what you value. And you said it: there are so many different tiers now, whether it’s ultra-luxury or modern luxury. We’re not really in a world anymore where the Ritz-Carlton chandelier is the one picture of luxury. That’s probably the biggest shift.

Luxury is so subjective. For one person it’s access, for someone else it’s thread count, and honestly, there’s nothing wrong with any of it. It’s just about what you personally deem valuable and what you’re willing to pay for.

Luxury travel can sometimes feel like it’s about access: upgrades, sold-out hotels, impossible reservations. What do you think actually creates the deepest client loyalty?

I think it goes back to the first question you asked me, which is that this is such a human business. What creates loyalty is really listening to people, making them feel seen and understood. And it’s not my favorite thing to say, but sometimes it’s the complicated situations — with a client or a hotel — that turn the tide.

It’s one thing to create a beautiful experience. It’s another when someone is in a bind, and you make sure they’re taken care of, and they know there’s someone to turn to. That sense of safety and knowing someone has your back while you travel is huge.

For example, over New Year’s, when Caribbean airspace shut down completely — or even back in 2020 with COVID — those are things we never thought would happen, and then they did. Reliability and follow-through is ultimately what creates loyalty.

I have an appreciation for people like yourself making the impossible possible behind the scenes. In recent years, what is the biggest shift you’ve seen in traveler expectations, particularly in the high-end segment? And what are some new skills that the best travel advisors need now that they didn’t before?

When a place becomes ultra-popular — like Capri, for example — the ultra-wealthy start to move away from it. Luxury is evolving because as certain places become more accessible and more crowded, luxury starts to shift into what isn’t accessible, what isn’t crowded. Then there’s also this pursuit of what’s undiscovered in the moment. What feels truly special now is the thing not everyone else is doing. So a big part of our job as travel advisors is staying ahead by scouting new destinations and building relationships in those places that unlock access to interesting experiences for our clients.

What are some example destinations?

You can take places like Antarctica — something like White Desert — as an extreme example of what’s not accessible to everyone. Parts of Africa, such as Botswana, are another good example. Or even in Italy: the Amalfi Coast and Capri, which I still love, but maybe now you’re looking for something a little more off the beaten path, like Pantelleria. Or take a property such as Amanpuri, for example. It’s been around for decades, but it’s still very hard to get into. They prioritize guests who have been coming for years, which is the right thing.

But that’s what luxury is shifting toward: gaining access to places that not everyone can.

So that’s what working with SmartFlyer as a guest or traveler gets me: access.

And it’s also that we have great, long-standing relationships with these properties and brands. At the end of the day, our collective buying power certainly helps in delivering for our clients.

Do SmartFlyer agents also vet the clients they work with?

SmartFlyer has about 250 agencies attached to our platform, and they all work slightly differently. Our advisors are considered some of the most elite in the space. They’re well respected, they’re high producers, and they’re very thoughtful in how they structure trips. They can’t do that in huge volume. Therefore our advisors are selective about the clients they work with.

How do you handle when a client’s expectations are unrealistic, especially at the high-end level?

At the high end, a big part of the job is setting expectations early. Sometimes it’s saying that if there’s a budget constraint, we need to be realistic about what’s possible. We will always deliver the best experience we can, but it’s important that everyone is on the same page from the start.

And if someone is asking for something that feels impossible, the truth is: almost nothing is impossible if the budget is there. That’s usually the simplest way to explain it.

Our advisors also aren’t personal assistants who just say yes to everything. They work collaboratively with clients or their teams to facilitate experiences and access. So it’s always a yes, within the constraints of the client. There are limits to everything, and clarity around that is what creates trust.

What’s your perspective on the role of AI and technology in luxury travel planning? What should be automated? What should never be automated?

There are a lot of things that should be automated. Internally, there’s so much operational work within an agency that technology can really help with, like itinerary building or certain booking platforms.

What should not be automated is the relationship side of it. Our advisors start the process by having a conversation with their client and get to know them. One of the biggest things we’ve always said is that we’re not experts in destinations, we’re experts in our clients.

Any great advisor can learn a destination quickly. What’s harder is learning the human element. I want to know what’s important to you when you travel. I want to understand why you want to go to a place, what the motivation is. Those are the nuances and they can’t be automated by AI.

Where is human taste irreplaceable? Because in reality, someone could tell ChatGPT that they value history and good food and wine, and then it’ll spit out an itinerary.

I think it’s a fair question, because you could absolutely go into ChatGPT and say: “I love history, I’ve never been to Rome, I want four great restaurants, I want art experiences, build me an itinerary.”

And chances are, it will give you a really solid basic itinerary. It’ll pull the restaurants that are already listed online, the museums everyone knows, the things anyone has access to. But AI is pulling from existing information. So if a restaurant has changed, if the chef has left, if something is no longer as good, that’s not going to be reflected quickly.

The bigger difference is the human element. It’s a conversation in person or over the phone to figure out: What kind of history are you actually interested in and why? What part of art moves you? What do you want this trip to feel like?

I had a client once who was obsessed with churches. Truly obsessed. They wanted to walk into every church in Italy. It was a celebratory trip, but they only had two nights on the ground. They wanted it to be undeniably special.

So then the question becomes, how do you take something that’s accessible and make it extraordinary?

We thought: what about the Sistine Chapel? But instead of doing it like everyone else, what if we privatize it? What if we take you in the evening, when it’s closed, and then follow it with an incredible dinner cooked by a private chef in a special, undisclosed location?

ChatGPT can’t do that. That’s the difference: it’s not just the itinerary, it’s knowing what’s possible, and knowing how to make something feel once-in-a-lifetime.

Everything AI knows is information that’s available to everyone. What a great travel advisor brings is education, relationships, access. That’s earned over time and is irreplaceable.

Surely not just anyone can call and ask to privatize the Sistine Chapel!

One hundred percent. It’s also the education; you have to know what’s even possible in the first place. It’s one thing to have relationships, and those relationships help open doors. But it’s also about having the knowledge, not just the access.

How do you explain SmartFlyer to someone who thinks travel advisors are just “booking agents”? What do you wish more people understood?

SmartFlyer is really ideal for someone who wants a full experience from start to finish, and who wants to build a relationship with a professional over time. We’re not just booking agents because we’re genuinely invested in our clients.

For example, we worked with a couple when they first came to us just planning a simple little getaway. A few trips later, about a year into working together, he called us to help him plan a proposal. So we planned it with him, based on what we already knew about him, what we knew about her, and what would make it meaningful for them.

And then they got married, had babies, and now we’re planning family trips for them.

That’s really the point. We invest in clients for the long term, because the more we know about you, the better job we can do. The farther away we are from simply being a booking agent, the more personalized and thoughtful the travel becomes.

It’s about being experts in the person. What do you care about? What do you not like? What are your interests? I joke, but not really, that we want to know as much about you as possible. The more context we have, the better the trip is going to be.

At this level, travel is no longer a casual purchase — it’s a major financial transaction. Clients are spending $100,000+ on a single hotel stay or hundreds of thousands on yachts and private aviation. The reality is, advisors at the high end are managing enormous sums of money and complex logistics.

In many ways, a great travel advisor is the equivalent of a financial advisor: someone you trust with high-value decisions, who needs deep expertise, strong relationships, and the ability to protect the client’s investment.

What does SmartFlyer do exceptionally well that is hard to replicate, even for other luxury agencies?

I always say we have a really deep bench of incredibly knowledgeable advisors. Our community is one of the most special parts of SmartFlyer. No one person can possibly know everything about the entire world down to the smallest details. So instead, we have this tight-knit network of experts who travel constantly, who are on the ground, and who have the most up-to-date knowledge of cities, hotels, and experiences everywhere.

For example, we have an outpost in Australia, so our advisors there know the Asia-Pacific landscape exceptionally well. That information sharing is critical for us, and it has always been one of our strongest pillars: this incredible collective knowledge that’s constantly evolving.

I think that’s a real point of differentiation.

And at the same time, it’s a small world. I’m a champion of the travel advisory industry as a whole. There are a lot of great agencies out there. It really comes down to what fits your preferences and what kind of relationship you’re looking for.

What’s a travel trend you think is overrated, and one you think is underrated?

Can we all stop traveling for Instagram? I would love to see that go away.

And what’s underrated is going deeper into a destination. Settling in, taking your time.

The trend used to be, “I’m going to do Australia and New Zealand in one week.” And it’s like, sure, you can, but you won’t actually see anything. I’d much rather see people immerse themselves in a place, stay longer, and return because you always rediscover new layers. Even for something like a safari trip, you can go over and over again and it’s never the same.

Life is short. Don’t save everything for someday.

When you’ve been to a place more than once, you also earn the ability to go off the beaten path. Of course there are places you should always see. If you’re in Rome, you should see the Colosseum.

Then the question becomes: what else is interesting beyond the obvious?

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