Solo founder Cat Jones took a big step in creating a travel company around the same time the pandemic hit Europe in March 2020. Now, in the summer of 2024, the tour operator has launched, side roadAramex has announced the closing of a Series A funding round worth £5.04 million (around $6.4 million at current exchange rates).
Jones believes that slow, sustainable travel — trips that have the unique advantage of being flight-free, and travel across land (and sea) by train, bus or ferry, allowing vacationers to enjoy the scenery and avoid crowds while relaxing in more remote locations — is a winner. She tells TechCrunch that growth has been 3x year-over-year, with more than 4,200 trips sold so far.
Environmental concerns are one of the main factors encouraging holidaymakers to find ways to reduce air travel. At the same time, many popular European tourist destinations – from Amsterdam and Barcelona to Rome and Venice – Even the well-known tourist islands Coastal cities are not considered hospitable to tourists as local communities suffer from the effects of overtourism.
These two trends were on Jones’ mind when she was looking for a startup idea after spending time as an investor at London-based startup accelerator Founders Factory. Before that, she spent a decade at digital advertising tech company Unruly, ending up on its executive team as global senior vice president of data.
The UK-based startup now employs 40 people. The Series A funding, led by Heartcore Capital with participation from Eka Ventures and angel investors, will be used to fuel expansion into new territories. The company said it plans to add more staff, including engineers, to further invest in its AI-based flight planning technology.
Right now, the majority of all-inclusive holidays Byway sells (around 60%) are booked online, meaning customers use its trip design software, called JourneyAI. The other 40% of sales come via its human-powered concierge service, where staff talk to potential customers to design a trip that suits their needs. But Jones is confident that its vacation planning tool will be able to take on more of the trip design work as it connects more data sources and improves its AI-powered recommendations.
Fun but flexible
Jones had always loved slower, more scenic forms of travel, taking the ferry to Ireland to visit her family, and having loved trains since she was a child, never having owned a car. So she saw a real opportunity to plan “fantastic” road trips – with stunning scenery and exciting travel experiences, such as the thrill of a ferry crossing, mountain railways, or slow-paced sleeper trains with dining cars.
Multi-stop road trips change the pace of travel, creating opportunities for a different kind of tourism that is less harmful to the environment than flying. They can also spread the economic benefits to more locations—relieving pressure on tourist hotspots. But planning such trips is complex. That’s why Byway’s AI tool is a critical component of scaling this type of alternative travel business.
So how does Byway’s trip planner know what kind of trip to recommend to each user? According to Jones, the tool draws on a wide range of information sources and context to build packages, such as transit schedules and fare information, as well as information provided by the customer themselves. The AI also looks at information Byway already has about previous trips that were well-received. In effect, its AI aims to match customers with similar travelers who have made them happy in the past.
Byway gives an example of the level of detail and context she tries to fit into these details: a couple on vacation might love the idea of a late-night sleeper train, while a family with kids is unlikely to be thrilled. “You have to be very responsive,” she says, adding that much of the work involved in designing Byway is dealing with all the “nuances” of travel and trying to sort them out.
The tool can also be used in a number of different ways. Customers looking for inspiration on where to visit can enter a few basics — like how long they want to stay away — and get suggestions for a complete vacation from scratch. For example, a week of traveling through the French countryside. Or a three-week trip across Europe to Turkey and back via Budapest and Vienna.
Or they can take inspiration from the pre-planned trips offered on Byway’s website and customize a suggested package to better suit their needs. So the 60% online booking rate seems like a testament to the plausibility of AI suggestions and the level of adaptability they already offer.
The technology also helps overcome a second major challenge of multi-leg flights: Journeys with lots of stops can easily be thrown off course by disruption somewhere along the chain. Jones says JourneyAI helps manage this disruption risk by designing for resilience, with the software considering return options so it can offer alternatives if the original plan goes off course.
“We’re still manually categorizing disruptions right now. But really, this is something that we’re going to be able to very soon — especially with this funding — automate the vast majority of disruption detection and automate disruption replanning,” she says. “So we can alert people and say, look, your flight is down here. Your train is a little bit late, you’re going to miss your connecting flight — here’s the reworked part that we’ve done for you. And then, yeah, definitely talk to us if you want to. But really, if you’re happy with it, you can just accept it and we’ll go.”
As another solution, Byway has created WhatsApp groups for customers to provide an easy way for them to reach out during their journey so they never feel like they have to deal with any issues on their own.
“We sell a complete holiday, which means that when a customer buys from us, if there is a fault, we take responsibility. We fix it. We settle it – which makes it easy for the customer to make a decision. [purchase the trip]“If something goes wrong,” she adds, “Pi Wei will text me and say, ‘OK, this is the disruption, and this is what we’re doing about it. Go get ice cream from so-and-so while you wait.’”
“But this also gives us, of course, an additional imperative with our technology — not only to design really fun roads, but also to design roads that have a level of resilience to disturbances.”
For transportation ticket bookings, she says they generally integrate with APIs provided by third-party aggregators, such as a Swedish startup everything is ready. Accommodation booking is also another part of the goods. The trip planning tool is the core intellectual property.
“We are a tour operator, not an agent,” she stresses. “This allows us to buy at commercial rates as a tour operator for accommodation and transport – meaning we are not looking at a very small commission where every penny counts and you have to deal directly in every case… [It] “This means that the focus of our technology can be on the really smart AI journey. We can spend most of our time doing something that no one has done before.”
Human experience in the loop
While the majority of Byway’s customers use its technology tool to design and book their trips, a significant number still want a human agent to help them plan their vacations. Travelers with personalized needs may find that automated suggestions aren’t specific enough. Others may prefer to have someone they can talk to involved in the planning process.
Still, Jones remains optimistic that the team can continue to improve the AI’s responsiveness and increase the percentage of flights booked through the tech toolpath. “It could be absolutely perfect!” she suggests with wry enthusiasm when asked by TechCrunch how good the AI recommendations are. “That’s what we’re investing in and why we’re raising money.”
“In a lot of cases, the technology does a really great job,” she adds, more seriously. “In fact, in the majority of cases, the technology does a really great job. But there’s that 40% where we need people to do it because we can’t manage it yet.”
“You can have this general model where we have certain local nuances, but increasingly, the more regions we go into, the more local nuances JourneyAI needs to have within it. But we’re kind of at a place where we go, ‘Oh my god, we understand it; we already know now that it needs this, it needs this, it needs this.’ And actually, the biggest problem we have is that we don’t have a lot of developers… So we have a back-end roadmap for JourneyAI but we don’t have enough back-end tech people to work as fast as we would like on that roadmap, and then the same thing on the front-end… That’s where this fundraising came from.”
She also stresses that humans have a key role to play in identifying high-quality content to feed into AI recommendations. To that end, she says Byway’s product communications team works with “destination management organizations” on the ground. In areas it doesn’t know well, it hires local journalists to help it build “a real data quality layer,” she tells us.
“You can’t go everywhere you could dream of with Byway, but the places you can go – we chose them for a reason,” she adds.
Elsewhere, as Bayway prepares for regional expansion, its team is busy with more routine tasks — such as resolving regulatory issues related to Brexit.
“We’re on a regulatory journey now,” she says, explaining that after the UK voted to leave the EU, her bond no longer applies to Europe – which is why Payway has set up base in the Netherlands. “We have to have a European company so we can have a European bond that protects our European customers. So that’s basically the next step… Once we have that, we can really start marketing to Europe.”
This report has been updated to correct the amount of funding raised.