2. THE UPGRADE · WEEKLY · The Ethics of Ai in Travel Planning
The Ethics of AI in Travel Planning, How Sonia Cheng Rebuilt Rosewood, Hotel Openings of 2026 On My Radar
🗝 The Upgrade · Weekly · by Anne Marie Brown
In this week’s The Upgrade:
• Pre-Departure: The Ethics of AI in Luxury Travel Planning
• The Room Report: One & Only Mandarina + How Sonia Cheng Rebuilt Rosewood
• The Lobby Bar: What’s Actually Happening with Rosewood, American Airlines Says No to United, Hotels Worth Hollering About (2026 Openings)
Travelers,
It’s Monday. My inbox is bursting with pre-arrival plans for summer travelers and a lot of newsletters about AI, because Claude is my current obsession. In this week’s The Upgrade: the ethics of AI in travel planning, a treehouse resort in the Mexican jungle, and the woman who turned a forgotten hotel brand into a global status symbol.
I’d apologize for the length of this week’s newsletter, but my therapist told me to stop apologizing so much.
Happy travels, Anne Marie
Co-Founder, Alpenglow Travel
The Upgrade is free for subscribers. Support this publication by forwarding it to your friends and booking your trips with us.
🗝️ Pre-Departure - Industry hot takes, what our team is working on
The Ethics of AI in Luxury Travel Planning
I’m fairly active on Reddit, and I’ve been following a community called Chubby Travel for about a year. The name has a long backstory, but the short version: it’s a welcoming corner of the internet where advisors and travelers talk about luxury travel without the usual gatekeeping. A month ago, I had the chance to meet Alex Barnes, the advisor who runs it, at a tech incubator hosted by our shared host agency, Coastline Travel. I may have fan-girled. Hard.
We spent two days doing a deep dive on AI in travel planning, and I haven’t stopped thinking about it since.
AI is still controversial in this industry. But the advisors who are using it well are absolutely outpacing your mom’s travel agent.
My team has gone deep down the Claude rabbit hole. I wake up at 3am watching Instagram reels on how to use it better. I send the team podcasts, training resources. I’m hooked.
Now, I want to be VERY clear: I would never use AI to design a client’s trip from end to end.
That’s a hard line for me.
Our job as advisors is to understand our clients at a level that no algorithm can replicate.
Claude might tell me it’s possible to hit three cities in Italy in seven days with two toddlers. As a parent, there’s no way I’m suggesting that unless I hate someone. The human aspect and 18 years of experience I have in this work is not a feature you can automate, and let’s be real, Claude gets it wrong as frequently as my business school classmates trying to show off, (that is to say, confidently incorrect).
Where AI genuinely helps is by freeing up the time a qualified advisor would otherwise spend on admin. Travel planning is a remarkably fragmented industry. We work across CRMs, itinerary builders, commission tracking, GDS platforms, plus the proprietary portals for every hotel and cruise brand (I see you, Four Seasons). I receive itineraries from destination management companies in live links, PDFs, Word docs. I book tours on Viator and GetYourGuide, restaurant reservations through concierges or OpenTable, transfers through Rolzo or Carey Limo.
Now I can pull all of that together into a beautiful, branded client document in a fraction of the time. I can also use it for quality control: flagging missing confirmation numbers, catching a transfer window that’s too tight, double-checking logistics I might have skimmed. I’m a very good advisor, not a perfect one, and having a second set of eyes that doesn’t get tired is genuinely useful.
Advisors using AI this way handle more reservations, service clients better, and free up time to build the hotel sales director relationships that actually matter when I reach out and beg for a client upgrade. I have become more efficient and excited in the past three months than I have since launching our agency.
I’m working on convincing Alex to let me do a full profile on her. Stay tuned.
🗝️ The Room Report - Personal reviews from my own travels
One & Only Mandarina: A Treehouse in the Jungle (with hazards)
If you aren’t on Reddit, it’s worth checking out. A significant amount of what AI search surfaces now pulls from Reddit, and it’s one of the better places to get real, unfiltered answers about travel. I moderate a small community there and post travel reports regularly.
My most recent is a full spring break review of One & Only Mandarina, north of Puerto Vallarta. Jungle treehouse situation set into a hillside above the Pacific. One & Only Mandarina is one of those hotels that had a rocky opening between the doldrums of Covid and reports of golf cart issues and service misses. I can confidently say they have fixed these issues.
Most unexpected bonus – a kids’ club my kids actually wanted to stay at so mommy could work by the pool without playing referee.
Most unexpected drawback – my 5 year old son’s arm getting sucked into a pool drain that wasn’t capped in the first five minutes of arrival at our beautiful jungle villa. He is fine. His arm looked like a giant hickey. I jumped in fully-clothed and may never sleep again.
🗝 Bonus Section: Master Key - Deep Dives on Hotel Brands. New this week, and back whenever we have something worth the deep dive.
Rosewood: How Sonia Cheng Turned a Sleepy American Brand into a Status Symbol for Modern Wealth
In 2011, a thirty-year-old took over a hotel brand most people in the industry had largely forgotten about. Rosewood Hotels was small, traditional, and almost entirely concentrated in North America. Her family’s Hong Kong-based investment group had just paid $229 million for it.
That thirty-year-old was Sonia Cheng, and what she did next is one of the more interesting brand transformations in modern hospitality.
Her stated goal was to build the Four Seasons for millennials (that’s me!): take a quiet collection of historic properties and turn it into a global status symbol for a new kind of affluent traveler. Younger, more culturally curious, and deeply allergic to anything that felt generic or performative.
She did it through three moves, each one a direct rejection of what the rest of the industry was doing.
She weaponized sense of place. Every major luxury chain spent decades perfecting the same formula: consistent marble lobbies, predictable room layouts, a brand identity so uniform you could be in Dubai or Denver and barely notice the difference. Sonia’s answer was to take Rosewood’s existing “A Sense of Place” concept and push it further than anyone had before. Rosewood Hong Kong doesn’t look like Rosewood Paris. Rosewood London doesn’t echo Rosewood Las Vegas. Each property is a cultural hub where locals actually want to be, not just somewhere travelers pass through.
She built a lifestyle ecosystem. Luxury buyers don’t just consume products, they seek identities. So she shifted Rosewood from hotel operator to lifestyle curator: Asaya, the brand’s wellness concept; Carlyle & Co., a members club; a coherent brand world with enough depth that you never want to step outside it. It’s why Rosewood resonates with younger wealthy travelers in a way legacy luxury brands often don’t.
She killed pretentious service. Modern luxury travelers don’t want stiff, formal, aristocratic hospitality. They find it exhausting. Sonia replaced the old rules with a culture that encouraged staff to show up as themselves. The result is service that feels warm and present rather than performed. Done well, it’s what keeps guests coming back.
The brand Sonia inherited was a footnote. What she built is one of the most interesting stories in luxury hospitality right now, and the pipeline my Rosewood rep walked me through last week suggests she’s just getting started.
🗝 The Lobby Bar - Hospitality updates, promotions, and the occasional pun
· American Airlines Says “No” to United
· Most Anticipated Hotel Openings of 2026 in the Luxury Sector
Q: How do you know your trip was planned by AI?
A: The hotel has perfect reviews and zero rooms.
What’s Actually Happening with Rosewood
First, let me kill the rumor. Marriott is not buying Rosewood. I asked my rep Nicole directly. I cried with relief. The brand is independent, healthy, and expanding fast.
They just rolled out “Rosewood 3.0,” a new logo and identity refresh. What matters is that their “sense of place” philosophy is still intact. Every property is built to feel unmistakably tied to its destination.
What’s opening and when:
Americas: Rosewood Calistoga is open now, 96 rooms with private residences on a brand new site. The Raleigh Miami Beach and Rosewood Exuma (private island villas) are both coming in 2027.
Europe: Rosewood Rome is projected for this fall. Blue Palace Crete pushed to Spring 2027. Courchevel opened last ski season and ran 90% occupancy.
Asia and Middle East: Amala in Saudi Arabia launches this year, Maldives next. Three properties coming in China. Unpublished but signed: Puerto Rico, Punta Cana, Milan, Sardinia, Seychelles, Kyoto, Tokyo, Seoul, Mexico City, and Costa Rica.
On Rosewood Mandarina specifically: I was just there for a site visit and dinner when I stayed next door at One & Only Mandarina (see above). My honest read: Rosewood is genuinely oceanfront in a way O&O is not. More open, warmer feeling, walkable. The beachfront rooms are beautiful, lots of light wood, private pools, direct surf views. It is, unfortunately, quite hot because it’s so exposed in contrast to O&O’s treehouse orientation. The Japanese restaurant was excellent. Beach bar Buena Onda has a stunning sunset, great ice cream, and aggressive mosquitos.
After last month’s Punta Mita cancellations, Rosewood has more availability and softer rates than usual. Rates starting at $800/night in May against a normal ADR of $1,500+. If you’ve been curious, now is a good time.
One flag: Kona Village has had reports of slow pool service, spotty room service, and housekeeping hiccups. Nicole acknowledged prior staffing challenges and believes things have improved. I’m watching it. Will report back.
Book through me via the Booking Portal or email AnneMarie@alpenglowtravel.com.
🗝 Happy Hoteling, Anne Marie
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Agree we can use AI but also need humans, appreciate the nuance