Just weeks into his new role as CEO of Despegar, Gonzalo Estebarena is outlining an ambitious vision for the Latin America-based OTA as it enters its next phase under Prosus ownership. Having previously served as Despegar’s CTO and chief commercial officer, Estebarena said the company has maintained its “startup soul” while gaining the scale and resources of a global technology company following Prosus’ $1.7 billion acquisition in 2025.

A major focus is artificial intelligence, with Despegar committing $100 million annually over the next three years to AI development while aiming to triple the size of the business. Estebarena said access to Prosus has accelerated conversations with technology partners and provided Despegar with a “front-row seat” to AI experimentation and innovation.

Expansion in Brazil is a key priority, particularly as Despegar works to become part of a broader Prosus ecosystem spanning travel, food delivery, entertainment and other consumer services. Estebarena described this strategy as targeting “life-decision moments” for consumers.

He also discussed Prosus’ development of a “large commerce model,” designed to predict customer actions rather than words, enabling more personalized offers and communications that drive transactions. The interview also explores Uber’s move into hotels, Despegar’s internal AI projects and the leadership challenges Estebarena faces as CEO.

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In this episode, the CEOs of CityUnscripted and Context Travel unpack how distribution in tours and activities is evolving as major platforms like Tripadvisor and Airbnb expand their presence. Nick Whitfield of CityUnscripted argues that while the landscape may appear increasingly commoditized, the reality is more nuanced.

Overwhelming choice and sameness across listings create friction for consumers, opening the door for differentiated experiences to stand out. He points to shifting search behavior, driven in part by AI, as a catalyst that could benefit more distinctive, experience-led operators rather than purely scaled marketplaces.

June Chin-Ramsey of Context Travel reinforces that differentiation will hinge on human connection. As definitions of luxury evolve, she sees a growing premium on meaning and personal attention rather than traditional markers like high-end amenities. Expert-led tours, she argues, deliver something technology cannot replicate. AI and augmented tools may enhance discovery and planning, but they will not replace the depth and authenticity of a knowledgeable guide.

Together, the guests highlight a fragmented but opportunity-rich sector where success will depend on clarity of product, thoughtful use of technology and a renewed focus on human-led experiences.

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The conversation around sustainability in tourism may feel more advanced than ever, but real change isn’t keeping pace. Jeremy Sampson, CEO of The Travel Foundation, argues that growing consensus on tourism’s environmental and social impact has created a misleading sense of progress. While awareness has increased, the system itself hasn’t evolved quickly enough to match the accelerating pressures of climate change and global instability. What the industry once expected to face years from now is already unfolding, compressing future risks into today’s reality.

As these challenges intensify, Sampson believes regulation will become a key driver of change, shifting more control to destinations whether the industry is ready or not. He points to initiatives like the Canary Islands’ RegNext program as examples of collaboration between governments and industry to support more sustainable growth. At the same time, reframing sustainability through the lens of economic resilience is helping bring more stakeholders to the table. Still, gaps remain between what consumers say and what they do, raising questions about how success in tourism sustainability should ultimately be defined.

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Hotels are actively exploring AI as a strategic investment, with a strong focus on improving guest engagement and operational efficiency. James Bishop of SiteMinder emphasizes that the real opportunity lies in automation, not workforce reduction, but enabling staff to work more productively. Chris Clayton of Scenic Hotel Group reinforces that AI is not a plug-and-play solution, warning against oversimplified expectations. Instead, hotels must carefully identify the right applications to drive meaningful return on investment, recognizing that AI implementation requires thoughtful integration rather than a one-size-fits-all approach.

Both guests highlight that success with AI hinges on data quality and readiness. Well-structured, accessible data is essential for AI to deliver value, while poor data leads to unreliable outcomes. The discussion also touches on how AI can enhance personalization and reshape the role of online travel agencies, all within the context of longer-term technology adoption cycles.

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Multimodal travel is quickly becoming central to how people plan and experience trips, according to Rome2Rio CEO Wendy Olson Killion. Speaking at The Phocuswright Conference, Killion emphasized that multimodal transportation—combining flights, trains, buses and more—is no longer a niche behavior but a core part of travel. This shift is reflected in Rome2Rio’s data, where 50% of searches now involve multiple modes of transport. She noted that short-distance travel, particularly within 90 miles, is seeing significant growth, signaling changing consumer preferences and a broader definition of how trips are structured.

Several factors are driving this trend. Regulatory changes, such as European Union restrictions on regional flights, are encouraging alternatives like rail. At the same time, cultural influence is playing a role, with celebrities and influencers reshaping perceptions of train and surface travel. Killion described this as the “surface rising,” highlighting the growing importance of non-air options. Beyond consumer behavior, she also discussed her first year leading Rome2Rio after transitioning from Expedia Group, and how the company is addressing challenges like overtourism. Together, these dynamics point to a future where multimodal travel is not just an option but the foundation of trip planning.

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Nishank Gopalkrishnan, six months into his role as CEO of Dreamlines, is focused on understanding both the cruise industry and how the company can stand out in a relatively under-digitized segment of travel. Drawing on experience across startups and major players like TUI and MakeMyTrip, he sees cruises as a fragmented market with significant room for innovation. Despite representing only a small share of global tourism, the cruise sector presents a major opportunity to modernize booking and packaging, which he and his team are actively working to reimagine.

A key pillar of this transformation is artificial intelligence, which Dreamlines is embedding into its rebuilt technology stack to drive more efficient and dynamic cruise packaging across both consumer and business channels. Gopalkrishnan also points to AI’s potential to enhance personalization, particularly within loyalty programs, while acknowledging broader industry challenges and his own early hurdles as CEO. Overall, his vision centers on leveraging technology to unlock a more seamless, personalized and scalable cruise experience.

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Travel companies are entering a far more regulated era as governments in Europe and the U.K. expand consumer protections to reflect how travel is now bought and sold. Historically, regulations like the Package Travel Directive focused on bundled trips, but new rules extend coverage to services purchased within a 24-hour window, even if booked separately across a single platform. According to Rhys Griffiths of Fox Williams, this marks a significant shift, potentially requiring more companies to obtain licenses and implement insolvency protections. As a result, businesses that once operated outside strict regulatory frameworks may now face tighter operational constraints and oversight.

At the same time, broader regulatory pressures are intensifying. The EU’s Corporate Sustainability Reporting Directive will require travel companies to disclose environmental, social and governance risks, including how climate change could impact demand patterns and business performance. Additional measures like the Digital Services Act are also increasing scrutiny, particularly around online content such as illegal listings. With penalties increasingly tied to company turnover, the financial stakes are high. Taken together, these changes are dramatically widening the regulatory net, catching many travel companies off guard as they struggle to keep pace with evolving compliance requirements.

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The airline distribution landscape is entering a new phase as New Distribution Capability (NDC) adoption accelerates and the industry moves toward modern offer and order models. In this episode, Jeremy Jameson, VP of the Americas at Mystifly, and Jesus Monzo Faubel, senior director of flights (west) at PKFARE, discuss how improved servicing and post-ticketing functionality are beginning to drive real operational efficiencies. While adoption still varies across airlines and agencies, both note that the foundation is now in place, with airlines in Europe and the U.S. leading the way through stronger content strategies and distribution approaches, while travel sellers continue to navigate technology and post-booking challenges.

The conversation also explores what comes next, including the growing role of intermediaries in bridging gaps across the ecosystem and making NDC content more accessible. Looking ahead, Jameson and Faubel highlight the importance of data and customer-centric retailing, emphasizing the need for robust data architecture to better understand traveler behavior. Combined with advances in AI, these capabilities are set to power more dynamic, personalized and responsive travel experiences as airline distribution continues to evolve.

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