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Why High Net Worth Individuals Never Book Their Own Trips
A 30-year habit. One trusted advisor. And a line that’ll change how you travel.

Back When Travel Was a Phone Call
Before booking engines.
Before 37 open tabs.
Before AI told you where to go...
Travel started with a conversation.

You’d walk into your local agency, like the one on the cover of Holidaymaking 1955, and someone would greet you by name.
They knew your favorite wine, your preferred cruise line, and which side of the plane you liked to sit on.
That wasn’t just service. That was real luxury.
Somewhere along the way, we traded all that for convenience.
But not everyone.
Because for some travelers, the golden age of curated travel never ended.
And I was reminded of that recently… in the most unexpected way.
And while 1440 gathers the world’s headlines…
Latest Luxury Travel News
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Baker’s Cay Resort in Key Largo just debuted its fully renovated Grand Cay and Grand Pelican Suites, complete with private terraces, direct Gulf views, and personalized concierge service. It’s part of the resort’s push to elevate its barefoot-luxury appeal for families and honeymooners alike. LTA
⚓ The Queen Mary Now Has a Members-Only Club
The historic Queen Mary in Long Beach now offers an annual membership program starting at $150/year. Members receive unlimited ship access, discounts on tours and onboard dining, VIP invitations to special events, and early booking opportunities for future experiences. It’s a new way to engage with a California icon. LTA
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National Geographic Explorer Jenny Dorsey traces the Bedouin roots of Emirati cuisine across the Rub' al Khali, the vast Empty Quarter desert. From dates and cardamom to underground ovens and camel milk, the journey shows how traditional food culture still shapes Abu Dhabi today.
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🖋 From the Editor
Why High-Net-Worth Travelers Don’t Use Online Travel Agencies
(And What They Know That You Probably Don’t)
The other night, I found myself at a dinner party, seated near a retired finance professional in his late 70s. Sharp. Quiet. Clearly didn’t need to worry about money, or much of anything else.
While others poked his brain about markets and dollar forecasts, I stayed out of it. Honestly, I felt a little sorry for the guy. It was like being cornered at a party and asked to explain inflation for dessert.
Then, halfway through a lull, he turned to me and asked,
“And you, Alex, what do you do?”
I smiled. “I help people figure out the best places in the world to invest their money… and walk away with memories instead of spreadsheets.”
His eyes lit up.
“Is that so?”
I nodded.
Later that evening, he found me again.
“So you’re in the world of travel, huh?”
I nodded once more.
And that’s when he said something that stuck:
“I never make any trip that hasn’t been curated and supervised by my travel advisor. She’s been with me for over 30 years.”

I asked him why.
Here’s what he told me…
1. “She knows what I like, and what I don’t, better than I do.”
Feather-free pillows. Quiet floors. Rooms far from elevators. The right kind of firm mattress. No humid places in August. No art museums before noon. He never has to explain it anymore; she just knows.
2. “She tells me the truth.”
If a hotel has gone downhill, she says so. If the ‘five-star’ safari lodge isn’t actually worth the price this year, I’ll never see it on an itinerary. “I don’t want glossy,” he said. “I want honest.”
3. “She makes things happen I didn’t think were possible.”
A private palace concert in Vienna. A canceled hotel room that magically reappeared. A reservation at a restaurant that stopped taking them. “Sometimes,” he smiled, “I think she calls in favors before I even ask.”
4. “She solves things before I know they’re a problem.”
Delayed flights. Lost luggage. Unexpected strikes. “I’ve had land transfers rebooked before I got off the plane,” he said. “She doesn’t wait for me to call. She’s already handling it.”
5. “She respects my time.”
She doesn’t send him 15 options. She sends two, the right two. “It’s not just about taste. It’s about trust. I know she’s already eliminated everything that wouldn’t make sense for me.”
Then he leaned in, with the calm certainty of someone who knows exactly what matters.
“People like me? We’re not loyal to brands. We’re loyal to people. Esther (that’s her name), she’s irreplaceable.”
So, here’s what I learned from him:
High-net-worth travelers don’t avoid Internet Booking because they’re snobs.
They avoid them because they’ve done enough travel to know what’s at stake.
Not just money, time, energy, and experience.
They know that real luxury isn’t found in filters or price sort buttons.
It’s found in trust.
In discretion.
In someone who already knows where to send you, and where not to.
Because the deeper you go into the world, the less you want to waste a second of it scrolling.
And the more you value someone who gets it right the first time.
📘 The Video Savvy Guide to Valle de Guadalupe
Beyond Napa: Valle de Guadalupe Is Mexico’s Quiet Wine Capital
Just one hour south of Tijuana, Valle de Guadalupe is the kind of place that whispers luxury instead of shouting it. Think rugged hills, desert light, and vineyards stretching into silence.
It’s not trying to be Napa or Tuscany, and that’s exactly the point.
With over 120 boutique wineries, design-forward hotels, and world-class restaurants scattered across dusty trails, Valle is where in-the-know travelers go when they’ve done Bordeaux, Sonoma, and Mendoza, and want something raw, flavorful, and utterly Mexican.
📺 In this week’s featured video, we’ll show you:
The best wineries to visit
Where to stay (design lovers, you’re in for a treat)
And the restaurants making waves in Baja’s culinary scene
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