Inside the Secret World of Ultra-Wealthy Vacations

What does a $400,000 summer vacation actually look like? Today, I'm talking to Hao Tang, a travel advisor who plans $100,000+ trips for some of the wealthiest families in the world. What does somebody get for $400,000 for 20 nights?

They're directly on the beach. It has a private butler. One of the villas has a private chef as well. You have your full-size pool, huge pool.

Today, we're going to uncover how wealthy people travel, plus the hidden psychology behind travel spending at the highest levels. I almost don't want to tell you this,

Because it's kind of my secret sauce. But

how you book luxury hotel stays for high net worth and ultra high net worth families. And I have an itinerary from a client that you booked an actual trip for, a $400,000 itinerary for a single dad and his kids. Can I put it up on screen? Can you walk me through this itinerary?

Of course. Happy to.

What's the price of this itinerary?

So it's roughly $400,000, give and take by a few, when you're accounting for the accommodation, the, the sum of activities, food, tips, and the private jet home.

For how long?

For— this is just under, I believe, 20 nights, just under 3 weeks. Let's call it 3 weeks.

So this is a $400,000 trip for 20 nights?

Yep.

I have questions. I have a lot of questions. What does somebody get For $400,000 for 20 nights?

Sure. So this is a family who needs a 3-bedroom villa setup at the minimum, or 3 bedrooms I should say. This is a trip to Turks and Caicos, so they're directly on the beach. They are in a villa that has obviously ample amount of space. It has a private butler. One of the villas has a private chef as well. You have your full-size pool, huge pool, Right. And you're on one of the best beaches in the world. That's just like the very high level, but there's much more that goes into it as well.

All right. So what did this client come to you with? What was the thing they wanted you to do for them?

They came to me and said, hey, we'd love to go take a summer trip with my children. And he actually said, hey, Al, I saw the trip you took last year to Turks and Caicos for your 40th birthday. I thought that was really cool. I would love to do the exact same thing. So this trip was actually inspired by my 40th birthday trip, which I stayed at Amanara in their villas and then at Como Parakeet in their villas.

Let's walk through the actual process because I want to take people behind the scenes of what is it like to arrive at one of these hotels? What's the check-in process? Quite different than when I checked in at a Holiday Inn.

Yes.

In my early 20s. It's very different. So let's walk through the check-in process. You get there, actually you walk out of the taxi. Okay. What happens?

So most of my clients, I would say, especially with resorts, we will actually arrange the transfers with the hotel. So the, so the experience starts not at the taxi when you arrive at the hotel, but at the airport, right? So as soon as you come off the airport, someone's already with a sign and then arrive at the hotel. And I will say this, The Peninsula always does a fun arrival in that because when you book their vehicle, when you pull up, there's 4 people out there waiting on you, right? Because the driver typically calls about 3 or 4 minutes out and says, hey, we're almost there. They come out, they have their pen, they have their notebook. You get out of the car, they whisk you into your suite to check in or your room to check in. You're not checking in at the desk? No, no, you're never checking in at the desk. You never see your luggage. When you get out of the car, Luggage is going to be in the room at some point in the next 3 or 4 minutes, like magic, right? And, and sometimes what I see them do is the team will ask you, hey, would you like a little brief tour before we take you to your room or suite first? And if you do that, they aim to get the luggage into your closet before you even check in.

Okay, so I get there, they're waiting to greet me, they take me up to the room. I don't go to any check-in desk. I'm now taken up to a room, to my room, and what happens next?

So this could happen in the room or sometime earlier. Every hotel is different, but they will usually have someone with a cold or warm towel depending on the location of the place and have welcome drinks for you and everything like that. And sometimes they may have a printout of your itinerary if you have an itinerary of things you want to do and, you know, things like that. And then once you've settled into your suite, they will ask you to obviously perform some housekeeping items like getting your passport and things like that. But then they will ask, hey, You know, if you guys are not tired, I would be happy to show you the suite and all the amenities and features and buttons and things like that. But if you're tired—

What's different in these suites versus like a Hyatt, you know, or any other hotel room?

There are a lot of hidden features. Like, for example, my TV is hidden somewhere in this room that you cannot assume, right? You cannot guess. So you have to know exactly how to access that. There are certain buttons, there are certain— some, some, like I stayed in a suite before where it had a hidden door. To the bathroom. I would have never found it on my

own. Why are these clients of yours— why do they care so much? For example, this is $15,000 a night for 8 nights at Aman Yara. $125,000, more than $15,000 a night. Whenever you hear somebody talking about numbers like this, it's really easy to say, that's crazy. What a waste of money. I can't believe people spend this. It's disgusting. So, I want you to use something I call the D2C principle. From disparagement to curiosity. Personally, I prefer to get curious. What do you get in a hotel room for $15,000 a night?

I would say, you know, one of the things I really love about beach properties is that there's really 2 very drastic ways, different ways to experience a beach hotel or beach resort, right? One is imagine the old school beach hotel in like Hawaii or something like that where you go into this Big complex, right? You have elevators, different floors with balconies and railings and everything. So every day you get up, you say, okay kids, okay everyone, pack your stuff up. Let's get our bag, go down to the pool. Let's go find some seats if we can find them. Hopefully we'll find them, right? Mm-hmm. And then let's make camp for the day, right? And if you, you know, like if you all of a sudden wanna take a call, if you wanna use the bathroom, I'm a bit of a germaphobe, so I don't like to use public restrooms. You're like, okay, do I really wanna dry myself off, get My sandals on, take the elevator, go back up, blah, blah, blah. So that's one way to experience it, which is still great, right? Growing up, never traveling at all, that's heaven. But imagine if you're on the most pristine beach in— on a private island and your room is directly on the beach. You take 3 steps out from your living room, you're on your private deck, half covered. In front of that is a gigantic pool just for you and your family. You can make all the noises you want when you have kids. You don't have to worry about anyone else. At any point in time, you can take 30 additional steps. Now you're on the beach by yourself. Take another 50 steps, you're in the water, right?

And what does it mean if, if you have a chef in some of these villas? How does that work?

It can be very different from different properties, but let's just use Amayar for, for example. So the chef will make anything you want, assuming that they have the ingredients. And sometimes if you would like, like for example, I have, I have some Indian clients who have very specific dietary needs and preferences, right? So for those clients, I love to always send ahead of time, hey chef, my clients do not eat these ingredients.

French food. They do not want French food because it has virtually no taste. They do not believe in pepper and rosemary as a seasoning. Okay, I understand. You send that ahead. What else?

Yeah.

So the chef gets these requests or these, like this list. And then what do they do?

They can customize a menu for them. But a lot of times, what's something that Aman's always known for is basically they can make anything off menu for you, right? So you can say, hey, listen, our family really loves Thai dishes. So one of the things that a lot of clients actually request by name is different types of chef at Aman. Some certain chefs are proficient in Thai food, some in Indian food, some in French food, etc., right? So these specificities are very important. And it's something that we also request almost like Requesting the room type.

Why not just go to the restaurant?

You can do that as well. All the options are available to you. One of the things that I've really loved when I've spent time there is that we actually, when we travel with children, what we do is we actually have the children eat at a different time. So we have the children eating at like 5:00 PM. We have the chefs make them grilled chicken, whatever the case may be. And then the kids all eat together and then they make a mess and then the butler cleans everything up. Everything is all nice and neat again. And then at 7 o'clock, after we kind of put the kids aside or to bed, then the adults come together and then we have our meal, right? So they have a different cadence to everything and different menu. So it's fantastic. I've also had travel with family there where some friends wanted Thai food, some friends wanted Italian food. It doesn't matter, all comes out. They'll just make whatever you want, right? So it's whatever you can envision that we'll try to execute.

Why do you think Your clients care so much. Like, why not just go to a restaurant like 99.9% of other people?

It's convenience. It's convenience. And I feel the same way, right? So for example, I go there every summer. I was just there this summer. And in the villa, you know, you have this idea of how the day is going to go before you go on your trip. You're like, oh, we're going to do XYZ. We're going to shower, dress up, go to the restaurant. But when you have kids, it's mayhem. It's 6 p.m. You know, my little guy is running around like butt naked with his diaper off or whatever the case. You're just trying to survive. You're like, I want dinner here now. I don't want to change. I want to be in my bathing suit and my t-shirt. I am in no mood to shower and then go get ready, right? Like, so it's convenience. I would say at the end of the day, so much of the luxury that you don't— that doesn't translate on a website is flexibility and convenience.

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They basically are with you at all times just to make sure that if there's anything you need, they can assist you with. And this could be make sure that there's always beverages, water, towels by the pool, et cetera. And with us, when we're traveling as a big group of friends or family, there's always a lot of mess, as you can imagine. Anytime they're not executing a request that's given by you, they're cleaning up, they're straightening things up, right? So like, that's really nice for someone who loves like being organized and, and I don't like clutter at all. That's like heaven to me. Mm-hmm. Someone's always straightening things up. And as, as a father, like that's one of the biggest annoyances of, uh, having a, having a kid playing with toys all the time. There's always a mess and that's always being cleaned up. So even on vacation, this is happening, which is, uh, it's, it's quite amazing. And then I would say in the example of Parakeet, this is one of my favorite butler concepts. So this butler not only looks after you when you're in your beach house, he or she will travel with you throughout the entire resort. They become your waiter, they become anything you do. So let me tell you where the magic is for that. If you were to go to the restaurant on day 1, your butler goes with you, he or she will know your drink preference. So for example, every time you sit down, you like to have a Diet Coke. with 2 slices of lemon, right, and half glass of ice. You say that once and you're— the rest of your trip is done. If your butler did not go with you everywhere outside of your room, which is what most butler services are like, you still may have to repeat that every time you sat down, right?

Mm-hmm.

So just small things like that. And the best thing about the butlers at Parakeet is that they're fantastic with children. And I hate to like talk about how much this relates to children because So much of this does that most of my clients, and myself included, one of the favorite hacks I always call it is that I have clients who arrives at Parakeet the first night, they would send me a picture. And 50% of the time the picture is something like they're having dinner and in the distance is the butler with their child. So the butler is almost like a nanny hybrid.

So this is like the dream. So they, they are at this nice hotel, they can be eating whatever food they want, or it's just like nice having a glass of wine, sitting watching the sunset.

Yeah.

And they know their kid is having fun and being taken care of.

Yeah. It's

like there's even for half an hour.

Yes.

Okay. Wow.

It's just amazing. Like, also think about this, right? So kids club is one of the biggest, like, amenities of, of, uh, resorts for families, right? So sometimes, uh, you know, let's just say your, your child's at the kids club and you're by the pool and it's time to pick them up. Instead of you getting outta the pool and kind of like snapping out of the moment you're in enjoying the place, you just tell your butler, hey, could you please go to the kids club, pick up John and, and, and Jamie and take them back to the room or whatever the case, or bring them here, whatever the case may be. Right?

You know, this is really interesting because when you're saying this, I'm into it. I love it. The idea that I only have to order sparkling water with limes once And then everybody knows it. I love that. Like, I love that hospitality and those details. I remember being at the Taj Hotel in Jaipur.

Yes.

And we were there with some friends and it was— we were having a dinner and it was getting a little bit late. They had kids and one of the kids was falling asleep. And I remember one of the staff members coming up and saying, would you like us to take the kids back to your room? And it was like, I, I had never seen that before. And I thought it was magical. Let me get this straight. They're going to take the kids back to the room. They have a key to get in. They're going to make sure everything's safe. I'm sure they're going to send a little note saying, hey, everything's good. Interestingly, the friends that we were with were not comfortable. So they said, no, no, no, we're okay. Even though it was becoming a, you know, a little bit like the kids were a bit irritable.

Sure.

And I asked him, I said, like, to me, I'm like, how come you don't do that? That's, that's, it's free. It's included. Why not do it? And she just, she said, you know, I'm not comfortable doing that. So I thought it was an interesting example. There are a lot of options at these really high-end hotels, but not everyone takes advantage of all of them. Like, I've stayed at places where there's a butler.

Yep.

And I'll text sometimes, can you arrange this or that? I asked my wife, I'm like, do you want them to pack for us? Because they can pack.

Right.

I hate packing. I'm like, please pack this stuff. I don't want to have to pack it. It also gives me an extra 2 hours on the last day to not have to sit there. And then she goes, no, I don't want them to. I like packing myself. And I was like, what the hell? What? But what I've learned is just because it's there doesn't mean everybody uses it. You find the same thing with your clients?

Yeah, for sure. And I think this, you know, not to get off tangent, but it's the same thing. It's like sometimes I'll go to a hotel The younger me, the college kid in me, if y'all went to a hotel and you tell me, hey, Hal, guess what? The minibar is included. The minibar is free. I would go bonkers. I would be just chugging Coke and eating gummy bears, right? And then whatever's left on the last day, I'm putting in my bag, right? Yes, totally. And now I don't. Like, my minibar sitting in front of me, I haven't touched it once. It's completely complimentary, right? Yeah. Uh, I mean, I'm not gonna go drink, you know, 80 grams of sugar just because it's free, right? So I think there's some, like, freedom in that and some satisfaction I take in that I've kind of gone through a And there's nothing wrong with, you know, taking advantage of things that you, you've paid for. That's part of the amenities, right? Enjoy it. But I think the older, the more experiences like this I do, the more the luxury and the joy I get is getting the experience I want at any given time.

Love it.

Not feel FOMO, not feel like I have to do anything, right?

Yeah. I, I remember once, um, because you've been my travel advisor for many years and you have learned that My wife and I don't really care for wine.

Yes.

We don't really drink that much. So sometimes when you go to these places, they'll have a bottle of wine waiting for you or some kind of like champagne. And we're just like, we're not really into it. And you found out that I love berries because as a kid, right, we couldn't basically eat berries. They're too expensive.

Yes.

So basically every hotel I show up to, there's a plate of perfect berries like laid out for me. And I truly feel like a kid in a candy store. I'm like, These are for me and, and they're free. And the irony is, at some of these places, they're quite expensive, these hotels.

Of course.

But the idea that everybody still loves something that is made for them, like somewhere, somehow this hotel had— they figured out that I like berries. And obviously that was through you. And you found out somehow because one day I probably casually mentioned it.

Yep.

So there was a lot of work that went into This strawberry appearing on this beautiful ceramic bowl. And to me, that makes me feel like I'm taken care of. Like someone is watching over me. And if I kind of really pull the, pull the thread, it's like, it's almost like being a child and knowing that somebody's out there watching over me.

I'm so glad you brought that up. Because I think sometimes, you know, one of the things I'm sure you've heard many times is like, hey, why would you pay so much for a hotel when you're just sleeping there? Sleeping at a cheaper hotel is the same as expensive hotel functionality-wise, right? But it costs money and resources and manpower to get to know somebody. So for, for me to get to know my— this is why I don't have a million clients. I can only have so many clients because it takes time to get to know each client.

Yeah.

And then when I give this information to the hotel, it takes the manpower, it takes the time and energy to go track down or source certain Amenities for these clients, right?

When something goes wrong, I want to talk about that. Like, what's the worst call you've gotten from a client?

I would say one of the worst calls is a client who was going to go on a safari, and they've been looking for this their whole life. She's in her 70s. She calls me and tells me that she has cancer, which breaks my heart. And we've been planning this trip for like a year and a half, by the way, and she's the nicest lady. So she tells me that. I immediately, you know, like part of my mind is heartbreak. The other part is, oh crap, we're in penalty. They've already paid $60,000 and it's fully non-refundable at this point. And, and that was a bad call because of one, of, of, of her getting cancer. Second is this is probably one of the most difficult challenges to overcome, especially for a safari property. It's not New York. No one's going to walk in last minute and just book a safari for $60,000, right? So this is where I had to go into problem-solving mode and try to be very creative and unconventional in ways to try to kind of make that work for her financially.

Did it?

Partially. I was able to find another client who was looking to go on safari. And I said, hey, I went to my client who had the cancer. Hey, what if I were able to find someone else who would be willing to go on safari? I can get them to change their dates a little bit. but you give them a bit of a discount on what you paid, right? So everybody wins. It's a win-win situation, so to speak, right? But this is where I think it's challenging. These are, these are some of the most challenging things because you're having very, very bad news. And then on top of that, you're compounding with another bad news that's devastating as well.

Yeah. Okay. Is there a hotel that everyone thinks is worth it that you don't?

I'm going to say a region maybe because there's so many. I think Europe in the summer, It's just insane to me, right? You could go to like Amalfi Coast, Positano, etc., or even on Lake Como. You could get an entry-level room at the top-level properties for €3,000, €4,000 per night. Uh, so we're talking about $3,600 to $5,000 USD per night, and you're getting a 300-square-foot, uh, 300-square-foot like closet.

So what if a client comes to you and says, I want to go to Positano? Yeah, what would you say?

Uh, I mean, we would have— depending on the client, if they know the market well, I wouldn't even have this conversation with them because I already know, right? I just know that this is where they want to go and that's most valuable thing. Because sometimes, you know, one of my jobs is to actually understand what it is that you value.

Yes.

On any given trip, it's not always money. It's not always the quote unquote bang for the buck, right? Or at least in that way, sometimes it's going to the south of France in the peak of summer, because that's where you want to be, right? Like, that is the most important thing, right? Just like New Yorkers in January want to be in the Caribbean. Like, that might be the only thing they care about, right?

You know, you once told me in a, in a very respectful way because—

Oh, shoot.

My wife and I love Rosewood Mayakoba. We just love that hotel.

Yeah.

We've had so many great experiences. And you were kind of like,

oh,

again, yeah, in polite terms, you're like, that hotel is a bit incongruous with the other places that you stay. Basically, it's not as nice. When I personally, I love it. And the reason that I love it and we love it is we've just had such warm experiences with the staff. We brought some of our friends there. And I thought it was— I thought that was a great observation because what I've learned is I don't always need to have the most expensive, the most nice. Sometimes it's like, what, what's easy for people to get to? Or in this case, like, what makes us feel really warm and taken care of? And it's, it's nice, no doubt. Rosewood Mayakoba is a very nice hotel. There are more expensive ones around.

Yep.

But I thought that was a good observation. That clients don't— just because you have money doesn't mean you're always spending the max amount.

Yes. Yes.

Who pays for your travel?

I make these like reels every year about how this works. So I pay for my travel. You know, I think last year, it's still on my Instagram, I made a reel last May about how I spent $300,000, but I got $1 million worth of travel experiences. And the point of that reel was that there was a several hundred thousand dollar delta And that delta was through either invitation or upgrades and things like that, right? So like a free stay is a free stay, but it actually costs me something if I don't like the place. I'd rather pay either full price or discounted rate to go to a place that I like and love and that my clients will also like and love potentially than go to a free place that isn't a good fit, right?

How do you tell in a few minutes if someone is going to be a great client or a nightmare client?

I almost don't want to tell you this because it's kind of my secret sauce, but I'm going to tell you, even the way they approach me to become a client is a flag. So if someone approached me and just says, how do you work? What's your fee? That's a flag. That's a red flag for me. My most high net worth clients have always approached me with, hey, Hal, we've been following you for some time. We really resonate with you. Are you accepting new clients?

Mm-hmm.

Right.

And

my—

What's the difference in the 2 approaches?

Well, I think one is the, the first example, they're still interviewing you and trying to figure out what it is that you can do for them, etc. I think the second one, they've already made a decision on you. They've spent time investing in you to see if you might be a good fit for them. And here's the thing, I think they must have other areas in their lives where they work with a top person, and that means that they know the top person are not necessarily looking to take on new clients. They're probably already at their max. Right. The top, the top accountant for their taxes, the top whatever it is, right? The top physician.

What is the average cost of a trip that you book for clients?

On average, probably the hotels starts at about $4,000 per night on average. Right.

Okay. And how many nights?

5.

Okay. What's the lowest price that a client books through you?

Oh, I booked a client for a few hundred bucks before, but More so that, you know, once I have a client, I have a client. And if they need to go to a place in like Kuala Lumpur where like the Four Seasons suite is like $300, you know, I still book that for them. Of course, once they're my client, they're my client, right?

What should someone look for if they are hiring a travel advisor?

So I joked with Allura last year, which she did not find this funny at all. I said, if I die, you and Beckett work with an advisor, but this is what you look for. I said, first, you must be able to tell if she or him, if their taste was developed, you must be able to see how their taste was developed, right? Meaning like you can see visually or through something that they went to these places and their taste or whatever their opinions are is kind of refined by these trips they've taken, right? Like it's through personal experience. That's very important to me. And they also must have a strong perspective on things, right? Like, that's very interesting to me. And also, they must have demonstrated some ability or capacity to think unconventionally. Because sometimes, like the example for the single dad, I got him a $40,000 upgrade. That deal, that stay was not going to be possible until I made that happen, right? I saw an opportunity for both the client and the hotel and then made that happen. But that was unconventional thinking, right? So that's big. And then of course I said, You know, they must be able to showcase that they're doing the right people, right? The right general manager and things like that have their kind of like hands on the pulses of the industry. So I think that's— those are things that are very important.

Why did you choose to do this job? Did you grow up going to luxury hotels?

No, we were so poor we didn't even go to motels. We, you know, my mom moved here as an immigrant. She was a housekeeper and a waitress raising me, which is why, by the way, I have such a soft spot for housekeepers at hotels. I started traveling when I first started working at Ralph Lauren, just here and there, because we had company discounts, right? That was huge. I could get into Le Suri on the Upper East for like $200, right, when it was like $800. And that was a splurge for me. I had to like save to get the $200. And I didn't even know what that was. I couldn't define it at the time, but I just had this vision of like, I wanted to know what's out there. I wanted to experience it. And then when I try a little bit of luxury travel, it really like resonated with me. I really found everything about luxury hotels to be interesting. In fact, I could just stay in the hotel all day. I didn't want to leave, right? Like, like, that's a big difference. You know, my friends and Laura were like, oh, let's go see this museum, let's go do this. I'm like, I want to stay in the hotel, you go. I just want to stay. I don't sit in the bed and just enjoy this space. I can't tell you why, right? The fact that I can actually add value to people's trip and it's immediate impact almost, right? Like, when I work in the corporate world, you work on a project and realize in like 2 years, who knows, right? But I could work, I could do something for Ramit, and when they take that trip, I will immediately know how that went, right? I mean, there's pressure with that, of course, but the reward is so substantial. And, and even for the wealthiest people who, who maybe don't lack in finance, but they lack on time, right? So to play a role in one of the most like pivotal assets or moments of their life and make an impact is really rewarding. You know, I would say like, there's nothing like, you know, we've texted before. I'm like, hey, how's it going? There's nothing like getting a picture from your client and you're like, dude, look at these blueberries. They're in individual shelves. Like those things, I'm getting a little bit of goosebumps. Like, like, you are just amazing. You know?

Like,

yeah, I get texts and messages like that all the time. And, uh, you know, it's just something that I couldn't do previously. And, and And I love that.

I love it too. All right, Hal, thank you for taking us behind the scenes of luxury travel. I appreciate your time.

Yep. Thanks. Cheers.

Thanks a lot. I find this whole conversation fascinating, especially because most people never talk about this publicly. I ask myself, hey, why would someone spend this money? If they can afford it, presumably they have a reason. What is it? It might not be something I care about, but But maybe I will one day, and the only way I can understand it is by getting curious instead of disparaging it. So if you use the D2C principle, you're going to see lots of new ways to think about money everywhere you go. If you want to see more of these videos going inside what spending actually looks like at the highest levels and why, leave a comment and tell me what you want to see next.