I was travelling and kept thinking, why is booking still so hard?
So much of it still feels more difficult than it should be. You spend ages searching, comparing, filtering, and trying to work out what is actually the right fit. Then even when you think you have found something, the pricing is not always clear and the final cost can end up feeling different from what you first expected.
A big part of the frustration for me was not just the search itself, but how cluttered the experience often felt. Too many popups, too much upselling, too many steps, and not enough clarity.
It made me realise that a lot of travel booking still feels tied to older systems and older ways of thinking. The industry has moved forward in many ways, but the search and decision experience often still feels behind.
That was one of the starting points for Travorro (travorro.com).
We kept coming back to a simple idea. What if people could explain what they actually want, instead of being forced through the same filters and comparison flow over and over again?
As we worked on that, one thing became clear very quickly. Understanding travel intent is not always simple. Even something like “summer trip” can mean very different things depending on where the person is and what context they are searching from. Timing, seasonality, location and preference all matter, but most platforms still do not handle that very naturally.
So the thinking for us became less about showing more options, and more about helping people make better decisions.
I think that is where travel search is heading. Less rigid filtering, more context, more conversation, and a better understanding of what someone actually means when they search.
I would be interested to hear how others in travel are thinking about this too. Do you think the future of booking is moving away from traditional search and towards something more conversational and intent-led?
Hi Luke, thanks for sharing your ideas here and welcome to the community!
I'd flip the narrative a little on this. I don't believe that booking is necessarily broken (otherwise a billion people wouldn't be able to book a flight or stay at hotels every year) but instead pricing is broken.
The problem with pricing in travel stems from the opaque nature of availability and how things are distributed. Here's a real example. I help a local hotel near my home in Tasmania and we put ONE room price on the OTAs (Expedia, Agoda, Booking) managed by a channel manager. Yet despite us having "one price" the same room is listed with various discounts/deals marketed by OTAs. I call these synthetic deals (my own term). This leads to guests searching multiple channels (including meta search) comparing the room rate and availability in a quest for "the cheapest price", for what should be one room rate offered in all channels.
Consumers are taught by aggressive advertising from metaseach such as Trivago to "not trust" the pricing and to go and compare (side note, Trivago were found by Australian Competition Consumer Commission for misleading consumers on this). All the online players point the finger at the hotel for manipulating their prices, when in fact the hotel is the source of truth. And this is just hotels. Similar story for flights, experiences, cruises, etc. And we haven't even got to the issues about availability - is the room or seat actually available at the advertised price (or at all).
Regarding AI booking, I don't think that consumers will go all the way down the booking funnel to purchase because they have been taught (ironically by the online companies who both created and benefit from problem) to not trust the price. Maybe you'll book direct with your favourite hotel chain or airline via AI - but for anything else, people will want to compare for themselves. Can an AI agent go off and search and compare on your behalf? Maybe....but it seems like a giant waste of energy to me that is not really scalable for millions of concurrent searches.
If you think of pricing/availability as a layer that any booking UX sits on, then any new form of UX will always inherit the underlying problems. So for this reason I don't see a new UX coming along that will change consumer booking behaviour until the underlying layer is solved.
Hopefully some other Travel Massive members who work in the engine room of travel distribution will share their thoughts on this!
My thoughts are that organic travel search will evolve and improve. AI assisted search doesn't return enough travel providers or booking sources and this limit has to bother travelers. It adds to the frustration. Definitely, a search system needs to know more about the users wants. Google search can still collect and build user profiles based on search/view history, but it's lacking the intensity of the conversation. It could feed gemini data to Google search to present highly useful search results. Yet, Gemini's not that popular yet. Google needs that search ad revenue, and the AI sessions won't give it. They make money from people sampling listings and ads.
The answer to your question might be in the matter of what is a conversation. If Google or Expedia or a travel agency website gives me lots of potentially great options/sources, I don't need that longwinded session on ChatGPT with its limited selections, etc. I'd rather just get right to the best providers of flights, hotels, tours etc. Trust is the thing like Ian is suggesting, people want trust first, then lots of great providers, IMHO.
This is a thoughtful take, and I can completely relate to the friction you’re describing.
From what I’ve seen, the problem isn’t just that booking is hard; it’s that most people aren’t fully clear on what they want when they start. They might say “summer trip” or “something offbeat,” but what they actually mean could be very different; slower pace, fewer crowds, more local experiences, or just something that feels different from their last trip.
That’s where most platforms struggle. Filters and comparisons can only go so far, but they don’t really help people figure out what suits them.
This is also why many travellers still prefer working with someone who curates their trip. Not because they can’t find options, but because there’s just too much noise and not enough clarity.
I do think things are moving towards a more conversational, intent-based way of planning. But the tricky part is understanding what the traveller actually means, especially in the early stages.
Curious to know one thing: when someone says something vague like “I want something different,” how does your platform guide them without making it feel complicated again?
Really appreciate both of your perspectives here. This is exactly the kind of discussion that sharpens the thinking.
I agree that booking itself probably is not the main issue. The bigger problem is what sits underneath it, especially pricing, availability and how things are distributed across channels.
What I’m building is much more focused on the discovery side of that journey. The idea is not to replace comparison or pretend trust is solved. It is more about helping people get to a better starting point faster.
Right now, a lot of people either work through rigid filters or jump across multiple sites trying to figure out what is actually relevant to them. I think there is room to make that part of the process a lot better.
If someone can describe what they want more naturally and get back options that are genuinely relevant, with live pricing, that does not remove the need to compare. It just reduces some of the noise earlier in the journey.
I completely agree though that any new interface still sits on top of the same underlying pricing and distribution issues. Until that layer becomes more transparent, there will always be friction closer to the booking decision.
That’s why I’m focused on discovery first, rather than pretending a new interface solves the whole problem.
Do you think the future of booking is moving away from traditional search and towards something more conversational and intent-led?
was posted by Luke
in
Discussion,Booking,Travel Tech,Future,Innovation.
Featured on Mar 31, 2026 (21 days ago).
Rated
5/5
★
by 1 member.
Sharing is caring
🎉 Link copied
Share
QR Code
Welcome to Travel Massive!
Discover new ideas in travel and join our global community of innovators and thought leaders. Learn more.
+ 202 others joined this month
Comments
I was travelling and kept thinking, why is booking still so hard?
So much of it still feels more difficult than it should be. You spend ages searching, comparing, filtering, and trying to work out what is actually the right fit. Then even when you think you have found something, the pricing is not always clear and the final cost can end up feeling different from what you first expected.
A big part of the frustration for me was not just the search itself, but how cluttered the experience often felt. Too many popups, too much upselling, too many steps, and not enough clarity.
It made me realise that a lot of travel booking still feels tied to older systems and older ways of thinking. The industry has moved forward in many ways, but the search and decision experience often still feels behind.
That was one of the starting points for Travorro (travorro.com).
We kept coming back to a simple idea. What if people could explain what they actually want, instead of being forced through the same filters and comparison flow over and over again?
As we worked on that, one thing became clear very quickly. Understanding travel intent is not always simple. Even something like “summer trip” can mean very different things depending on where the person is and what context they are searching from. Timing, seasonality, location and preference all matter, but most platforms still do not handle that very naturally.
So the thinking for us became less about showing more options, and more about helping people make better decisions.
I think that is where travel search is heading. Less rigid filtering, more context, more conversation, and a better understanding of what someone actually means when they search.
I would be interested to hear how others in travel are thinking about this too. Do you think the future of booking is moving away from traditional search and towards something more conversational and intent-led?
Hi Luke, thanks for sharing your ideas here and welcome to the community!
I'd flip the narrative a little on this. I don't believe that booking is necessarily broken (otherwise a billion people wouldn't be able to book a flight or stay at hotels every year) but instead pricing is broken.
The problem with pricing in travel stems from the opaque nature of availability and how things are distributed. Here's a real example. I help a local hotel near my home in Tasmania and we put ONE room price on the OTAs (Expedia, Agoda, Booking) managed by a channel manager. Yet despite us having "one price" the same room is listed with various discounts/deals marketed by OTAs. I call these synthetic deals (my own term). This leads to guests searching multiple channels (including meta search) comparing the room rate and availability in a quest for "the cheapest price", for what should be one room rate offered in all channels.
Consumers are taught by aggressive advertising from metaseach such as Trivago to "not trust" the pricing and to go and compare (side note, Trivago were found by Australian Competition Consumer Commission for misleading consumers on this). All the online players point the finger at the hotel for manipulating their prices, when in fact the hotel is the source of truth. And this is just hotels. Similar story for flights, experiences, cruises, etc. And we haven't even got to the issues about availability - is the room or seat actually available at the advertised price (or at all).
Regarding AI booking, I don't think that consumers will go all the way down the booking funnel to purchase because they have been taught (ironically by the online companies who both created and benefit from problem) to not trust the price. Maybe you'll book direct with your favourite hotel chain or airline via AI - but for anything else, people will want to compare for themselves. Can an AI agent go off and search and compare on your behalf? Maybe....but it seems like a giant waste of energy to me that is not really scalable for millions of concurrent searches.
If you think of pricing/availability as a layer that any booking UX sits on, then any new form of UX will always inherit the underlying problems. So for this reason I don't see a new UX coming along that will change consumer booking behaviour until the underlying layer is solved.
Hopefully some other Travel Massive members who work in the engine room of travel distribution will share their thoughts on this!
My thoughts are that organic travel search will evolve and improve. AI assisted search doesn't return enough travel providers or booking sources and this limit has to bother travelers. It adds to the frustration. Definitely, a search system needs to know more about the users wants. Google search can still collect and build user profiles based on search/view history, but it's lacking the intensity of the conversation. It could feed gemini data to Google search to present highly useful search results. Yet, Gemini's not that popular yet. Google needs that search ad revenue, and the AI sessions won't give it. They make money from people sampling listings and ads.
The answer to your question might be in the matter of what is a conversation. If Google or Expedia or a travel agency website gives me lots of potentially great options/sources, I don't need that longwinded session on ChatGPT with its limited selections, etc. I'd rather just get right to the best providers of flights, hotels, tours etc. Trust is the thing like Ian is suggesting, people want trust first, then lots of great providers, IMHO.
Hi Luke,
This is a thoughtful take, and I can completely relate to the friction you’re describing.
From what I’ve seen, the problem isn’t just that booking is hard; it’s that most people aren’t fully clear on what they want when they start. They might say “summer trip” or “something offbeat,” but what they actually mean could be very different; slower pace, fewer crowds, more local experiences, or just something that feels different from their last trip.
That’s where most platforms struggle. Filters and comparisons can only go so far, but they don’t really help people figure out what suits them.
This is also why many travellers still prefer working with someone who curates their trip. Not because they can’t find options, but because there’s just too much noise and not enough clarity.
I do think things are moving towards a more conversational, intent-based way of planning. But the tricky part is understanding what the traveller actually means, especially in the early stages.
Curious to know one thing: when someone says something vague like “I want something different,” how does your platform guide them without making it feel complicated again?
Really appreciate both of your perspectives here. This is exactly the kind of discussion that sharpens the thinking.
I agree that booking itself probably is not the main issue. The bigger problem is what sits underneath it, especially pricing, availability and how things are distributed across channels.
What I’m building is much more focused on the discovery side of that journey. The idea is not to replace comparison or pretend trust is solved. It is more about helping people get to a better starting point faster.
Right now, a lot of people either work through rigid filters or jump across multiple sites trying to figure out what is actually relevant to them. I think there is room to make that part of the process a lot better.
If someone can describe what they want more naturally and get back options that are genuinely relevant, with live pricing, that does not remove the need to compare. It just reduces some of the noise earlier in the journey.
I completely agree though that any new interface still sits on top of the same underlying pricing and distribution issues. Until that layer becomes more transparent, there will always be friction closer to the booking decision.
That’s why I’m focused on discovery first, rather than pretending a new interface solves the whole problem.