In August, travel protection provider Faye secured $50 million in its Series C round, led by Madrona, with plans to use the capital for expansion and AI development. Hotel distribution specialist HyperGuest also landed $25 million in September to fuel international growth.
In December 2025, AI-powered travel platform Mindtrip received an investment from Capital One Ventures and United Airlines Ventures. While the amount was not disclosed, Mindtrip said the investment brought its total funding to $22.5 million.
One startup also changed hands, with blockchain company Chain4Travel scooped up by Travel Token Marketplace in February for an undisclosed amount.
We touched base with three members of our 2025 class, Byway, D3x and Faye, inquiring about their highlights from this year, their thoughts on AI and what challenges lie ahead.
Byway
London-based Byway helps travelers plan flight-free trips across the U.K. and Europe, packaging train, bus and ferry transportation with accommodation.
2026 highlights
- Byway secured a £1M+ loan from Innovate UK to further automate the personalization layer of our trip design. This funding was in addition to £500,000 in grants that the U.K. government provided to support Byway’s innovation efforts
- This summer, we celebrated 25K passengers traveling on Byway trips since our launch in 2020.
- Despite the disruptions caused by wildfires, extreme heat and strikes in 2026, Byway has maintained a high and ever-increasing customer net promoter score, regularly hitting over 80 each week and a Trustpilot score of 4.9/5, with travelers praising our in-trip disruption replanning.
- In July 2026, we launched Byway Club, a multimodal, flight-free rewards program. It rewards customers for traveling by rail, ferry and coach with increasing discounts, flexibility and exclusive experiences across repeat no-fly trips.
- We made the brave decision to share some Byway business secrets by offering a free online course on how to DIY a multistop European rail trip. This supported Byway’s mission to help more people discover Europe and beyond by traveling through, not flying over and gained strong press momentum.
What is the biggest challenge your company is currently facing?
Climate change is reshaping travel, driving “coolcations” to northern climates and shifting peak demands to shoulder seasons as travelers avoid extreme heat. This shift from traditional beach holidays to mountain and lake trips is changing the face of travel. Byway’s biggest challenge is using its pioneering technology to help travelers build flexible, no-fly trips across these shifting locations and seasons. By facilitating flight-free rail and ferry travel alongside local accommodation, we help customers navigate changing environmental and geopolitical landscapes seamlessly, avoiding increasing airport disruptions and costs while actively reducing the carbon footprint of their journeys.
Where is AI having the biggest impact on your business?
AI impacts Byway on two fronts. Externally, consumer LLMs frequently generate logistically infeasible overland itineraries, leading travelers to bring these complex, broken plans to Byway to fix. Internally, we’ve developed our proprietary Journey AI technology, which trained on 2 million miles of proprietary routing data to build the most enjoyable routes possible. Also, our operations, sales and support teams have been leveraging AI to vibe code tools to drive process improvements and efficiency.
D3x
D3x provides AI agents for hotels to help with guest communication.
2026 highlights
- Launched Phone AI, delivering on the voice ambitions we outlined last year. At one property, it handled 8,500 calls in August, with 43% requiring no escalation to a human.
- Welcomed Iconic Hotels and Resorts as a customer, extending D3x’s reach into the luxury segment, where expectations of personalized service are especially high.
- Responded to 2 million guest messages and 300,000 emails, with average AI customer satisfaction scores across our properties on par with those of human agents.
What is the biggest challenge your company is currently facing?
Maintaining quality as the pace of development accelerates. AI lets us write more code and build features faster, but testing edge cases and making those features dependable for enterprise customers still takes time and judgement. Our challenge is ensuring that our ability to generate software doesn’t outpace our ability to validate it. There’s a commercial challenge too: In a market crowded with AI promises, we need to make quality tangible through measurable results and consistent performance in daily hotel operations.
Where is AI having the biggest impact on your business?
Our capacity as a team. Four AI agents support sales, customer support, product and coding, helping us serve a growing customer base while keeping our team below 20 people. Getting value from them takes investment in the processes, infrastructure, integrations and oversight that make their work dependable. That investment lets our people focus more time on work that needs their judgement. It also gives us direct experience of the value we deliver to hotels: the ability to improve guest service and handle more demand without expanding headcount.
Faye
Faye provides whole-trip coverage for travelers, including protection for health-related issues, lost or damaged belongings, pet care and trip disruptions.
2026 highlights
- Raised $50 million in Series C funding, bringing Faye’s total funding to $100 million and its valuation to half a billion dollars, fueling our next stage of growth and global expansion. This comes on the heels of opening our larger U.S. headquarters in Richmond, Virginia, to accommodate our growing team.
- Surpassed $100 million in annual sales, marking a major growth milestone less than four years after launching and demonstrating the demand for a more modern approach to travel protection.
- Expanded our partner ecosystem across OTAs, travel software providers and short-term rentals, with airlines and cruise lines soon joining the Faye fold. This growing network builds on already-existing partnerships with notable brands like Guesty and U.S. News & World Report, further embedding Faye across the travel journey.
- Doubled down on product innovation with new coverage options for budget and luxury trips, multitier plans for greater flexibility, parametric payouts for delays and cancellations and complimentary lounge access during delays, with even more fintech features on the way.
- Accelerated our investment in AI, with a focus on automating claims, advancing underwriting and risk assessment, and enabling faster development of tailored travel protection products for major partners.
What is the biggest challenge your company is currently facing?
Faye’s innovation has naturally created attention—and sometimes fear—amongst the competition. More specifically, legacy insurers concerned by our growth have actively sought to disinvite Faye from industry events. We see this purely as validation, while simultaneously being disappointed. Healthy competition breeds innovation, which in the long run is better for travelers and travel companies alike. As we continue to raise the bar, our focus remains on innovation, showing travelers and partners that a fundamentally better travel protection experience is possible.
Where is AI having the biggest impact on your business?
AI is having its biggest impact on claims and moving us closer to a claimless future for travel insurance. We’re working toward automating the entire claims journey, from intake and document review to eligibility checks, decision making and payment. AI can understand claim circumstances, analyze documentation and resolve straightforward cases without human intervention, while allowing our experts to focus on more complex situations. By year’s end, we expect AI to autonomously resolve more than half of all claims, with 75% of the remaining claims completed on first touch.
