Are algorithms actually making our trips better – or are they optimizing the serendipity out of travel? | Canada Voices

Théodora Armstrong’s latest book is Welcome to Sunny Town.

My first trip with a boyfriend was a six-week backpacking trek through Thailand in 1999, when I was 20 years old. We bought two airline tickets, and that was it. We didn’t book hotels or arrange other transportation. We didn’t organize any tours or plan any sightseeing itineraries. We landed in Bangkok with only a guidebook and hopped in a taxi, heading straight for Khao San Road. The recommended hostels were either booked or too expensive, so we wandered the neighbourhood until we found a vacancy. We didn’t own cellphones, and social media was years in the future, but even if we had camera phones and digital profiles, there was nothing Instagram-worthy about the place we stayed. I never thought to take a picture of the closet-sized room overlooking traffic chaos on the street below. Yet decades later, I still vividly remember the spot. It represented independence.

A few years after that trip to Thailand, I married the boyfriend, and we continued our adventures around the world, though our approach to planning trips evolved over the years. Now, instead of guidebooks, Instagram is my default source for travel inspiration, and lately, I’ve been investigating AI-generated itineraries. The trips seem to want to plan themselves these days. Any vacation talk in the vicinity of my phone triggers the algorithmic synapses, and before long, my feeds are inundated with holiday suggestions. It’s hard not to be lured by these curation engines parading flawless travel content, but lately I’ve been wondering how our digital ecosystems change the way we plan a trip or experience a destination. Are algorithms actually making our trips better? Or are they optimizing the serendipity out of travel?

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My freewheeling approach to travel in the nineties wasn’t unique. In fact, it was a common rite of passage for twentysomethings with the means for an airline ticket. There was a different kind of idealization around travel at the turn of the century. We wanted to wander aimlessly with a stranger around a foreign city like in the movie Before Sunrise. Was there more willingness to surrender to fate back then? Were we more resilient outside our comfort zone? Or did we simply not have a choice? Forced to navigate paper maps, we often found ourselves lost. The spontaneity of travel before smartphones could be many things at once: thrilling, mystical, frustrating, lonely. But for better or for worse, we often came away with a better sense of ourselves, and wasn’t that the point of travel?

Since having kids, my husband and I wouldn’t attempt a trip without concrete plans and hotel bookings. But I still seek out those under-the-radar experiences free of selfie queues. For instance, on a recent trip to France, I took my family on a day trip to Versailles. For an extra €10 we secured a tour of the King’s private apartments, which allowed us to skip the ticket line and access off-limit areas of the chateau with a guide – well worth the modest add-on fee. Afterward, we joined the masses in the grand corridors, everyone converging on the Hall of Mirrors, an influencer Mecca. A quick search will uncover hundreds of photos of the empty hall with influencers posed in princess-core dresses, channelling their best Marie. There are online guides laying out strategies for getting ahead of the crowds to get the best shot, which include arriving an hour before opening, and beelining for the hall, ignoring 400 years of history along the way – the goal no longer baroque architecture or a window into court culture, but an aesthetic photo pinned to the grid, magically free of the literal crush of tourism.

Instagram, especially, has fundamentally reshaped our travel ambitions, changing the way we view destinations. A holiday becomes social capital; a picturesque cityscape becomes a visual brand; cultural cuisine becomes a viral moment. Last year, anti-tourism protests escalated across southern Europe, most notably in places like Barcelona, where frustrated residents got worldwide attention after warding off tourists with water guns. The stunt may have been playful, but the frustration was real as residents dealt with a housing crisis, overcrowding, and the touristification of historical neighbourhoods, local shops replaced by souvenir stores and picture-perfect brunch cafés designed for social media.

AI developers claim their technology can solve overtourism by catering to the individual. In recent years, Open AI and Chat GPT have been partnering with travel giants like Booking.com and Expedia, promising more efficient planning tools and trip personalization. Instead of viral reels funnelling throngs of tourists to the same lookout point along the cliffs of Santorini, AI vows to find less crowded alternatives, in theory alleviating pressure from these congested destinations. But the new technologies are far from perfect. A 2025 BBC article reported two tourists were intercepted by an experienced guide as they prepared to trek through the Peruvian mountains in search of the “Sacred Canyon of Humantay,” a hallucination existing only in the neural network of an AI bot. Mistakes such as this are not only costly and frustrating but can be deadly for travellers setting off on outdoor adventures with incorrect information. A 2026 Forbes article cited a recent study by travel insurance company, InsureMyTrip, which found AI models could deliver professional-looking itineraries, but on closer inspection were often flawed with inaccurate pricing, inefficient travel directions, and even imaginary restaurants with made-up reviews.

Over time, the technology will likely improve, but models will still draw their information from our algorithmic echo chambers. Are we served by continually being fed more of what we already enjoy? Or does that kind of influence insulate us from true soul-searching and growth? Isn’t travel the ultimate vehicle for discovery, the best way to escape our lives and ingrained biases, and broaden our minds beyond the limits of our imagination, or the limits of an AI system built on our history of clicks? None of this even begins to account for the environmental impact of data centres. Isn’t it a bit ironic to use yet another extractive technology as a tool for exploring all the beauty and cultural diversity the world has to offer?

I recently published a novel about a group of expatriates in Japan, an experience my husband and I lived for a couple of years premarriage during the early aughts. The research I did primed my algorithm for Japanese travel content. For months, my feed was bombarded with tempting activities: a monorail ride through a mountain village in Nara; an enchanting cat island in Tashirojima; the must-try viral cream-stuffed sandwiches from Tokyo. Truth be told, I wanted to do all these things. The algorithm had my number. Taking in these reels, I was hit with both nostalgia and regret. We lived in Japan for two years, but we missed out on so much.

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One night, I told my husband we should have searched out more unique food when we were in Japan. I expressed dismay that we were in Nara, but never rode the monorail. But later, I remembered the true impact of my time in Japan and the experience had nothing to do with tourist traps or must-sees. I was 23 when I moved to Okayama. Two weeks after I landed, the Sept. 11, 2001, attacks changed travel forever. Those years abroad were challenging in so many ways I hadn’t anticipated. Nothing was optimized, but instead often confusing or straight up exhausting. I had to learn how to drive on the other side of the road, how to communicate without speaking the language, how to cook with new ingredients, how to make friends in a place where I didn’t know anyone. There were also beautiful experiences like the day my students guided me through a tea ceremony, or picking oranges in a seaside town with my Japanese teacher.

An algorithm would never create an itinerary for that life overseas because it would be disorganized, and demanding and unpredictable. The algorithm wouldn’t anticipate how those challenges made me more resilient and instilled in me appreciation for another culture. Algorithms take the easy road, because it’s much less effort to convince me I want an island full of cats or a must-try viral cream-stuffed sandwich. If we choose to use these tools, we should remember their limitations and make room in our travel for the unexpected. Even I couldn’t predict that the unplanned moments in a trip were going to be the most important moments of my life.