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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