The Solo Traveller
Your independence, passion, and lifelong memories.
Tools and Tech
Photographer: Hernan Caputo | iStock
AI can plan our journey. Should it?
By Geoffrey Williams and Josh Chandler
Briefly …
From dorm-room guidebooks to data-driven planning, travel tools have evolved. But when efficiency becomes the goal, what becomes of our innately human curiosity and instinct?
Long before AI began generating itineraries in seconds, travel advice was democratised by students working on the floor of a dorm room. In the early 1960s, Oliver Koppell assembled the first Let’s Go guide as a practical resource for travellers who assumed Europe was financially out of reach. What began as a stapled collection of advertisements, tips and hard-earned advice grew into a publishing phenomenon that spanned more than 90 countries and lasted over six decades.
Remarkably, the guides were researched, written and edited almost entirely by Harvard students, not seasoned industry insiders, but young travellers learning as they went. The appeal was not technological efficiency, but proximity – real people translating unique lived experiences into global access. And for many of us, Let’s Go was not only the inspiration, but our much-loved travelling companion from whom we were inseparable.
Today, itinerary planners powered by ChatGPT can generate a coherent multi-day plan in seconds, and for time-poor solo travellers, this unparalleled compression of research time is compelling. The administrative burden of travel planning – accommodation options, transit routes, and logistics – that once nested in the well-thumbed pages of our travel bible, can now be synthesised into a readable schedule without days and days of manual comparison.
Efficiency, however, is not neutral. When optimisation becomes the primary value, the day can begin to resemble a productivity spreadsheet rather than a lived experience. Over-structured itineraries leave little room for drift, and drift is often where solo travel does its most memorable, and often subtle, work. The danger is not speed itself, but the assumption that a well-optimised day is the same as a well-experienced one.
“The danger is not speed itself, but the assumption that a well-optimised day is the same as a well-experienced one.”
AI planners can cross-reference preferences across vast datasets and return sharp and specific results. A traveller interested in, say, brutalist architecture in Berlin can receive hyper-specific recommendations that would otherwise require hours of research. This kind of micro-personalisation can make destinations feel immediately accessible and tailored. Algorithmic personalisation, however, tends to reinforce declared preferences, or more of what we already know we like. Solo travel, at its most transformative, often disrupts preference rather than confirming it. If the algorithm protects us from discomfort too effectively, it may also protect us from the unpredictability that makes travel memorable.
Precision, patterns, and practicality
In complex transport and transit environments, AI tools can cluster activities geographically and reduce unnecessary backtracking. For solo travellers navigating unfamiliar systems alone, that logistical clarity can inform and enhance our confidence and safety. When routes are pre-clustered and days are neatly mapped, however, spontaneity becomes an inefficiency. The café discovered while lost, the unexpected street food stalls, or the decision to sit longer than intended because the quality of the light has changed – these quintessentially human moments resist optimisation and do not rank highly in algorithmic logic.
AI planners can filter suggestions according to our budget constraints, which can be a significant consideration for solo travellers who do not share accommodation costs. The ability to quickly identify neighbourhoods, transport passes, and activities aligned with financial parameters can reduce stress and increase accessibility. Budget filtering can also flatten nuance. Value is rarely equivalent to price, for example, and cost-effective recommendations drawn from review aggregates may prioritise popularity over atmosphere, or volume over intimacy. AI may identify the ‘best-rated’ option, but it cannot yet evaluate the quality of quiet … or human curiosity and perspective.
“AI may identify the ‘best-rated’ option, but it cannot yet evaluate the quality of quiet … or human curiosity and perspective.”
What is without question is the extent to which AI planners are responsive. A traveller in Barcelona who decides to avoid crowded indoor spaces can instantly generate alternative outdoor suggestions. This flexibility mirrors one of solo travel’s core freedoms, which is the ability to pivot without negotiation or compromise. However, constant recalibration can subtly shift our relationship with place. When every decision is mediated through a device, the habit of looking up, asking locally, or simply wandering may weaken. The itinerary becomes an ongoing dialogue with a machine rather than an evolving conversation with the destination.
For first-time solo travellers, AI-generated structure can function as reassurance. Even if not followed precisely, a pre-built plan provides a sense of containment and reduces anticipatory anxiety. This may encourage people to take their first independent journey who might otherwise hesitate. Confidence built on scaffolding, no matter how carefully assembled, can either strengthen our independence or delay it. If our itinerary remains purely external, the decision-making muscles we rely on daily may not fully develop before we need them on the road. Solo travel has long been a practice ground for self-trust, and the question is: Does AI support that growth or provide a convenient substitute for it?
Bias, fatigue, and usefulness
This is not simply philosophical speculation. Everyone has an opinion about the purpose and usefulness of AI in our lives, and these opinions can range from rusted on fear and suspicion to a love affair with the dazzling new horizons that the technology illuminates for us.
Recent research shows that conversational AI tools influence not just the nuts and bolts of planning, but the psychology of our travel decisions themselves. Our trust in the suggestions and their perceived usefulness shape how we engage with AI recommendations, subtly nudging our choices even before our first flight takes off.[1] At the same time, decades of work on ‘decision fatigue’, or the notion that repeated choice making erodes our ability to judge the merits of a recommendation, help explain why travellers might lean on AI planners in the first place, and why over-reliance could dull critical judgement.[2]
Algorithmic bias research reminds us that no model is neutral, and recent studies have shown that even large language models can over-emphasise certain destinations and under-represent others, a form of bias with real cultural and economic implications for the very reasons for our journey.[3]
AI planners do not merely organise information, they help shape the decisions we make. Empirical research supports this shift, with a 2024 study showing that AI-driven tools significantly influence travellers’ intentions and choices, particularly when the recommendations feel useful and trustworthy.[4] Even mainstream travel reporting has begun to question AI’s role in shaping journeys, noting that while algorithm-generated plans can cut through complexity and save hours of research, they are not infallible and still require travellers to exercise judgement and local awareness.[5]
In recent tech reporting Wired explored what happens when you hand over the mundane details of a vacation to AI, concluding that the experience was “not terrible”, but requiring clear human oversight to iron out errors and strange suggestions.[6] Meanwhile, travel columnists have documented how AI planners can confidently recommend attractions on days they’re closed or steer users toward pricier options because of hidden biases in their underlying data, which illustrates that ‘convenience’ does not guarantee ‘accuracy’.[7] In direct head-to-head tests conducted by industry outlets, some AI tools worked better than others, highlighting genuine disparities in reliability and usefulness.[8]
Beyond the tech media, AI’s influence on travel planning is beginning to draw mainstream cultural attention. Major outlets have reported that a growing share of young travellers are turning to AI tools to design their holidays, not just for convenience, but as a first step in deciding where to go and what experiences might matter. This shift suggests that AI isn’t merely a back-room research assistant anymore but is becoming part of the cultural conversation about what it means to plan a journey.[9]
From dorm-room floor to data centre, the tools that shape travel have evolved dramatically. What has not, and will never change, is why we travel in the first place. AI can organise, suggest, and optimise, but it cannot replace judgement, curiosity or instinct. Those remain stubbornly, and necessarily, human.
References
1. Al-Romeedy, B. (2025). ChatGPT as an emerging digital travel advisor: effects on travel decision-making. Journal of Theoretical and Applied Electronic Commerce Research, 21(1).
2. Pignatiello, G., et al. (2020). Decision fatigue: a conceptual analysis. Journal of Health Psychology, 25(1), 123–135.
3. Muellner, P., et al. (2025, August). Multistakeholder fairness in tourism: what can algorithms learn from tourism management? arXiv.
4. Kim, J., et al. (2024). Effects of AI ChatGPT on travelers’ travel decision-making. Tourism Review, 79(5), 1038–1057.
5. How AI tools are reshaping Aussie travel plans: benefits, risks. (2026). The Canberra Times.
6. Hernandez, J. (2025, June). I let AI agents plan my vacation, and it wasn’t terrible. Wired.
7. Elliott, C. (2025). Can I trust AI to give me good travel advice? Elliott Advocacy.
8. Lee, J. (2025). Do these AI travel tools really make booking easier? AFAR.
9. Dalton, T. (2025, October 7). Almost a fifth of young UK adults use AI to design holiday, study finds. The Guardian.
Geoffrey Williams is The Solo Traveller Group’s Founder and Publishing Curator, and Josh Chandler is a devoted solo traveller and writer who is based in Europe.