The growing gap between ambition and execution across the travel ecosystem

Hi I’m Tony. My background is from Intrepid Travel where I was inducted into the company Hall of Fame for outsized contribution to the company. Since late 2022, I’ve been going deep on AI + Travel. I share some of what I find here each week and interview people who are building cool AI things for the industry on a podcast.

I also partner with CEO’s, Founders and their boards on making sense of the opportunities with AI in their companies.

Virgin Voyages hits the bleeding edge twice in one week

A big week for Virgin Voyages. On the AI front they have released ROVEY which they are keen for everyone to know is definitely NOT just a chatbot.

“It’s a system made up of seven connected modalities, each designed to solve a different layer of the Sailor experience.

Together, they create something simple: a voyage that feels more intuitive, more personal, and more connected at every step.

  1. Connection brings everything together into a single, living Sailor profile.

  2. Constellation understands behavior and anticipates what comes next.

  3. Context powers natural, conversational interaction.

  4. Curation delivers the right recommendations at the right time.

  5. Choreography ensures every interaction happens when it should.

  6. Confidence equips our Crew with real-time insights.

  7. Concert continuously improves the system through feedback.

Seven modalities. One seamless experience.”

Part of Project Ruby, Virgin Voyages have partnered here with Google Cloud. “This wasn’t a vendor relationship. It was co-creation.” they said. The infrastructure used here includes BigQuery, Vertex AI, and Gemini to create “a new intelligence layer designed to connect every part of the Virgin Voyages experience, from the moment a Sailor starts dreaming about a trip to the moment they’re already planning their next one.”

“Sailors” are what Virgin Voyages calls its customers.

“Sailors can interact with Rovey conversationally — asking questions, exploring options, and getting guidance without navigating multiple systems.

Ask about itineraries, and Rovey narrows options based on travel style — not just dates. Curious about Shore Things? Rovey surfaces experiences aligned to individual preferences. Comparing cabins? Rovey provides clear, contextual guidance.”

I know what you are thinking but this is definitely NOT a chatbot.

For mine, this was the second most impressive thing Virgin did this week. The first was its redefining of what the travel industry looks like when it comes to creator marketing.

Virgin Voyages hosted 1100 creators and their partners/families for a cruise this week. Richard Branson himself was there.

Chief Brand and Marketing Officer at Virgin Voyages, Nathan Rosenberg said “We had more than 1,100 creators and their guests on Scarlet Lady for a voyage built to be lived first and shared second.”

The premise here was simple. No scripts or directives. Virgin backed its product to deliver and told creators to go explore and find whatever they loved most - and talk about that.

2025 saw consumer brand Unilever go all in on creator. Now travel has its champion in Virgin Voyages. They said they were going to flood the zone - and they did.

They now have a period of massive amplification in a key sales period, all the content they could ever need for the next 12 months of posting and they will have identified winning content to be used in paid campaigns.

Videreo is the place where your brand can find the talent to flood the zone too.

Contact me to learn how we can make this happen for you.

This content is provided by the newsletter sponsor Videreo.com

The growing gap between ambition and execution across the travel ecosystem - HBX

HBX (Hotelbeds) this week dropped survey results that showed there is a widening gap between ambition and execution in the travel ecosystem.

The core point in case was personalisation.

“This gap is particularly visible in personalisation. While widely prioritised, delivery remains inconsistent, with data integration (39%) and proving ROI (34%) cited as the biggest challenges.”

I was surprised by the ROI challenge. Is it because the personalisation isn’t working as a tactic overall? Or whatever version had been built internally was specifically not performing? Surely if it was working, the ROI would be obvious in increased sales?

Perhaps the bigger question is whether slapping AI on legacy systems or rebuilding with an AI native mindset is really the issue here?

UBER taps AI so you can book hands free and then starts selling hotels

The goals of being the super App of the West won’t die at UBER.

This week they added the AI capabilities to build a conversational assistant so “whether you’re running through the airport with kids in tow or have your hands full with groceries, our AI powered Voice Bookings will help you catch a ride in no time.”

Hotels are now also on UBER. “Uber introduced a partnership with Expedia Group (NYSE: EXPE) that allows Uber customers to book hotels directly in the Uber app, unlocking immense value for travelers.”

And to tie it all together they dropped Travel Mode “a new experience within the Uber and Uber Eats apps, offering travelers curated recommendations on local favorites, popular tourist destinations, OpenTable reservations, Uber’s version of “room service” delivered directly to your hotel door, and even forgotten items for those traveling to new destinations. Users can now think of the Uber app as a personal travel concierge.”

If they can just massage and haircuts delivered on demand in there and they might just beat Airbnb to its punch.

UBER + AI should also be able to do sightseeing to at least the proficiency of a hop on hop off bus right now - but that wasn’t one of the announcements for this week at least.

Clarasight raises $11.5M as the AI money continues to come for managed bookings

Business travel continues to be an area where AI funding continues to flow in travel.

Whilst not everyone agrees whether trip planning is a pain or a joy for leisure travel, when it comes to business travel, following policy, chasing up and submitting results and everything else that takes you away from the work you are actually trying to complete - the answer is clearer cut.

A digital EA doing the work is more than fine here for everyone and Clarasight are right in the middle of that.

“Clarasight, an AI platform for enterprise travel and expense, has raised an $11.5 million Series A led by AlleyCorp, with participation from Rackhouse Venture Capital, Clocktower Ventures, Pulse Fund, Thayer Ventures, Future Back Ventures, Vestigo Ventures, and XYZ Venture Capital.”

And the ROI question that affects other AI decisions is also pretty obvious here. “Enterprise customers using Clarasight have reduced reporting and insight delivery time by 99% while eliminating more than 90% of the manual data review cycles that previously consumed their teams.” Less review cycles = more actual work getting done.

Half of people no longer care in customer service is AI or human

In further signs that the general population is softening in its views of AI, a new survery by Ada found “50% of respondents are indifferent to whether their travel problems are resolved by artificial intelligence or a human agent, so long as the issue is resolved quickly and effectively.”

Sounds pretty obvious when you say it out loud…..

Of course there is still quite a bit of nuance at play. “The survey found that 24% of travelers would be more loyal to an airline offering 24/7 AI service, but 28% said a single poor AI interaction would decrease their confidence in the airline. More than half (53%) of respondents expect human support to be available at all times, even when AI is used.”

Make sure your AI is good. And when your AI gets out of its depth, move to human fast.

Samsung moves to organise travel within its wallet

Can Samsung connect a trip that is otherwise disconnected?

That is their bet with their new feature called “trips”. “A Trip timeline automatically groups eligible items like tickets and bookings for faster access during a journey.”

This seems like the old version of Tripit before it got bought and hidden away.

“Users can manage a range of travel-related experiences, including bookings such as hotels, flight itineraries, car rentals and excursions — as well as tickets for buses, trains, theme parks and sporting events.”

Whilst that all sounds great - there are inevitably 50% of things that don’t have tickets or don’t have compatible tickets. So whilst “Trips also supports the ability to manually add itinerary items and include memos alongside saved items to capture key reminders, plans and notes throughout the journey,” no-one is really actually going to do that.

Whilst this wasn’t necessarily an AI story - what does go into that wallet seems like a good personalised database from which AI could then become useful to fill the gaps without the need to manually enter things?

That was my thought anyway.

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Anti-surveillance pricing regulation looks to upset AI powered dynamic pricing

A little snippet from Maryland who are introducing legislation to outlaw “Algorithmic or technology assisted pricing.”

Apparently the EU is looking at something similar.

I wonder what this could mean for pricing negotiations versus just putting up prices based on the perceived ability of someone to pay?

The theory of the agentic world is my agent negotiates with a number of vendors and comes back to me with the best offer. This is all algorithmic and technology assisted…..

Slack Group!

The Slack group is full of the brightest minds in ai in travel.

This week there was a lot of chatter about orchestration layers.

Join the Slack group here (I found my co-founder Adrian in this group of over 220 of the top voices in AI + Travel)

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Most clicked last week was the link to the ClickRaven piece on SEOs being able to report those using AI spam tactics to outflank them.

That’s it - you’ve made it to the end of this edition. If you are getting some benefit from this newsletter - you can always buy me a coffee.

I’ll be putting the result of the most clicked post in next week’s edition so you can see where others are focusing. If I’ve missed something, you’ve got a tip or any feedback at all - you can simply reply to this email and it will come straight to me. I’m doing this for You so please don’t be shy to tell me what you think

Glossary

Artificial Intelligence (AI) Artificial intelligence leverages computers and machines to mimic the problem-solving and decision-making capabilities of the human mind. (source IBM)

Generative AI (GAI) is a type of AI powered by machine learning (ML) models that are trained on vast amounts of data and are used to produce new content, such as photos, text, code, images, and 3D renderings. (Source Amazon)

Large Language Model (LLM) is a specialized type of artificial intelligence (AI) that has been trained on vast amounts of text to understand existing content and generate original content.

ChatGPT - Open AI’s LLM; sometimes referred to by its series number GPT3; GPT3.5 or GPT4. These are used by Microsoft & Bing.

Gemini - Google’s suite of LLM.

If wanting to go even deeper into the AI lexicon - check out this handy guide created by Peter Syme for the tours & activity sector