As part of our new “Travel Writers Test AI Travel Advice” series, we set our correspondent loose on the streets of Tallinn, Estonia. First, Thom Brown rigorously follows an itinerary generated, on demand, by ChatGPT. Then, Lonely Planet’s “Estonia, Latvia & Lithuania” takes over.
Specs of dust twirl in the funnel drawn by a solitary streetlamp. The glass door rattles but doesn’t budge. Inside, chairs perch upside down on circular tables and a blind screens the counter. I’m here for my scheduled 8:30 am breakfast, but the café is well and truly shut. It wasn’t my own volition that brought me to this point, locked outside a train station market in the twilight of Tallinn, Estonia. I’m following an itinerary put together by ChatGPT, an entity that has never seen the world. For the day, artificial intelligence is my master.
Here’s the prompt I gave ChatGPT: “I need you to plan me a day trip in Tallinn. It’ll be for the Christmas period. Please be detailed, I don’t want to be bored. I also don’t want options. Tell me exactly what to do. And be warned: you’re competing against Lonely Planet.”
AI tends to give open options, but I want a strict itinerary. The rule is to follow it as closely as possible, doing exactly as ChatGPT demands–nothing more, nothing less. If something isn’t feasible, I can ask for new suggestions.
At 9:00 am, the door unlocks, the blind lifts, and I can finally fulfil the tasks set by Master GPT. A cabinet full of cakes and pastries reveals itself and my confidence begins to wane.
“Can I have, erm, an eggs Benedict with salmon, please?” ChatGPT assures me the fats and proteins will fuel a packed day ahead. The waitress tilts her head and squints.
“We don’t do eggs,” she finally confides, already exasperated by her first customer of the day. I take a cinnamon roll and a cappuccino and shuffled sheepishly to a corner seat in this empty, half-lit coffee shop. The day begins not just with an awkward encounter, but a deep-seated disappointment. I love eggs Benedict. This is a small café, though, not the promised trendy brunch joint. Tomorrow, a human-written guide from Lonely Planet will take charge, so today, I just have to grit my teeth and plow ahead.
The next stop is an obvious one: Tallinn’s renowned Christmas market on the Town Hall Square. What isn’t obvious are the oddly specific instructions provided by the master:
- Go early. Beat the crowds.
- DON’T buy anything yet.
- Take one full slow loop of the town square.
- Buy one mug of hot glögi. Even in the morning. This is Estonia. It’s fine.
- Buy ONE handcrafted item.
- Stand still and silent for 3 minutes near the Christmas tree. Then leave. Don’t linger.
It’s nice to outsource the planning, but I feel like a robot completing pointless tasks (cut to ChatGPT rolling its artificial eyes: “Welcome to my world”). Nonetheless, I surrender to the challenge. After a single loop, I pick a stall that’s still setting up and browse their glögi selection. One is mixed with the local liqueur for a total strength of 21%. Sounds perfect at 10 am on a still-rumbling cinnamon-dusted stomach.
“Tere, can I get the Vana Tallinn glögi, please?”
The blonde-haired vendor, still flustered from arranging gingerbread cookies, releases a sharp flow of breath.
“Okay, but be careful.”
“Oh, is it strong?” I ask, feigning innocence.
“Yes, and it’s early!”
“I know. I’m doing a challenge. Basically, ChatGPT has planned my entire day. I have to do exactly what it tells me.”
When you say you’re doing a challenge, you can get away with anything. She wishes me luck as I load the steaming plastic mug with raisins and orange slices. I browse the half-open, sparsely packed market, each ethanol drop on my tongue further relaxing my muscles and raising my thus far diminished spirits. Returning the empty cup earns back the two-euro deposit, which I endeavor to spend on a handcrafted souvenir. The closest option is a wooden juniper spoon for €2.50. The blunt-faced, round-headed bald man in a puffer jacket doesn’t understand the challenge, but agrees to the discount.
“Smell it,” he demands as I depart in search of the impressively tall Christmas tree at the square’s center. ChatGPT probably intended the next three minutes to be a powerful moment of meditative reflection. Instead, impatience creeps through my glögi-soaked capillaries. After all, the ice rink calls my name. That’s where ChatGPT’s out-of-the-box thinking really shines. I’d never have gone ice skating alone, but there are few feelings as freeing as slicing through the crisp air as sunlight finally begins to wash over the medieval church spires. A teenage couple embraces in the corner while an older man in hockey skates effortlessly twirls in the expanse of this otherwise empty rink.
The four of us exist independently in our own worlds, tranquil on the purity of a sheet of undisturbed white, which mirrors the paper-like sky above. It’s not sunny, but it’s mild with no threat of rain. I do one more lap, quickly this time with a confidence acquired over the last hour, and hop off the ice for a day that mostly consists of hot chocolate and museums dotted around the Old Town.
Legs now a little wobbly and eyelids increasingly heavy, it’s a good sign that the afternoon seems more open. ChatGPT leaves a gap of two and a half hours to look inside a church, a feat the most pious backpacker alive would struggle with. One clear benefit of using AI is that it’s adaptable. It’s already personalized to my interests and the time of year. Although I have to do what it tells me, I can request suggestions when a gap in the itinerary emerges. Yet, for some reason, it doesn’t want me to leave the Old Town. There’s so much more to Tallinn. An entire day in this small area is growing wearisome. But it tells me to continue exploring these “charming backstreets” and “authentic souvenir shops” (the robot’s words, not mine) until it’s time to hit a hilltop viewpoint for the sunset at 4 pm.
It’s 3:50 pm on the shortest day of the year as shadows fall upon the stone staircase on the side of Toompea hill. Below, soft yellow light bursts from lampposts, buttering the cobbles below. The sunset–if it ever existed–is long gone. Still, the city lights twinkle and the silhouettes of towers from the Middle Ages burst out of the scene into the fading navy blue sky. In the distance, ferries bob on the rocky sea. I consider how I’d like to have visited the seaside, but it’s not on today’s agenda.
Later that evening, the restaurant recommended by ChatGPT is overflowing with diners. They can’t fit me in. Full credit to the AI for suggesting a table reservation–advice I did not heed. The host, in his perfectly pressed black shirt, recommends some alternatives, leading to a place called Pegasus, where I spend €22 on three bites of impossibly flaky fish. Naturally, the food suggestions offered by my artificial master do not exist on the menu. This doesn’t bode well for what comes next.
“Go to Sigmund Freud bar. Order Zombirella. No hesitation. No conversation with the bartender. Just say it.”
What a strangely specific and strict demand. After the breakfast debacle, my faith is shot. What even is a Zombirella? Imagine walking into a bar alone on a Saturday night and confidently ordering a fully fabricated cocktail.
There’s something cartwheeling in my gut as I push the heavy arched door that’s carved into the jet black exterior of the bar. A waitress stands inside the entrance, her perfectly straight teeth gleaming as if expecting my arrival.
“Can I help you?”
Expecting a regular bar where you seat yourself, my mind isn’t quick enough to respond.
“I… well, it’s just me. Can I–can I just get a drink, please?”
“Of course, right this way.” She sits me in the corner–always my preference–and hands over a catalogue of cocktails. I glance down, then back up into her eyes that appear onyx in the shadow cast by her silky black bangs. She senses I don’t need the menu.
“Did you already choose something?”
“Zombiella,” I butcher the name, but she nods and floats over to the bar.
The length of time I spent silently standing at a Christmas tree this morning passes before a cup the shape of Sigmund Freud’s face plonks onto my table, adorned with a thick plastic straw and a hedge-worth of aromatic foliage sprinkled on top.
“It’s real,” I beam, mesmerized by the absurdity of it all.
“Huh?” the black-eyed waitress questions.
“Oh, I’m doing a challenge. I have to do whatever ChatGPT tells me to do and it told me to come to this exact bar and order this exact drink. It’s gone badly so far, so I’m just happy the drink exists.”
The waitress laughs, perhaps out of politeness, before explaining the elements of the drink, including the slab of brain-shaped white chocolate that floats on the surface. The Bacardi-based beverage isn’t to my liking, but that’s beside the point. I sip it dry, pay the €12, and ask ChatGPT to suggest a new bar.
Sunday morning, my body aches. I calculate that yesterday, I spent nearly 15 hours circling the Old Town on an LLM’s orders. The Lonely Planet itinerary begins a little late at 11 am, skipping its first suggestions to visit the Old Town Square and Christmas markets. This one-day itinerary has much more variation and I’m excited to see different parts of the city. First, it’s the Great Guild Hall, a hub for merchants and artisans since the 14th Century. Next, the ornate mushroom-domed Alexander Nevsky Cathedral, which Lonely Planet tells me was set to transform into a planetarium in the 1960s, but controversially remains a Russian Orthodox church. These are two of the best spots in Tallinn Old Town. I’m amazed ChatGPT didn’t suggest them.
After that, it’s lunch in the graffiti-sprayed home of creatives, the gentrified factory neighborhood of Telliskivi, followed by a 20-minute tram ride to the leafy suburbia of Kadriorg Park. From there, I soak in classic art at the KUMU gallery, then venture yet further out of town to the Communist memorials that punctuate Maarjamäe. This is where I catch the weekend’s first glimpse of a sunset as shades of orange bleed through the blackening cityscape of Tallinn’s Old Town that lines the coast around the corner of the bay. It’s colder today. Two hoods synergize to protect my face from the biting sea breeze. I sit on a grassy slope and reflect on the day. Nothing went wrong and I saw parts of Tallinn that I wouldn’t expect on a typical day trip to Tallinn.
Of course, taking an itinerary from a book means it can’t be personalized or adapted. But what comfort I find in implicitly trusting the information on the page. Every step guided by ChatGPT is accompanied by underlying apprehension and distrust. Yes, Lonely Planet may become outdated (which is why they update their books so regularly), but every stop comes with a paragraph that I know has been thoroughly researched and considered. AI-generated content has a tendency to hallucinate (or, as far as I’m concerned, outright lie to my face).
This day has been far more relaxed. While ChatGPT is determined to confine me to the boundaries of Tallinn’s 800-year-old stone walls, Lonely Planet implores me to head for suburbia. The book also bestows knowledge that I wouldn’t consider seeking out, such as the etiquette for entering a stranger’s home. ChatGPT only offers what I ask for; it requires an input. Even then, the suggestions aren’t always what I want. At one point, it seems to have run out of ideas, ordering me to observe locals grabbing coffee. It’s an order I obey and an activity as dull (bordering on creepy) as it sounds. Admittedly, though, there’s a certain child-like thrill in the unpredictability.
The final stop on Lonely Planet’s agenda is dinner and drinks in Noblessner, a reimagined port directly north of the Old Town. This book has taken me a long way from the center, so it’s a bit of a journey back, which I inexplicably attempt on a combination of foot and e-scooter. After navigating a cluster of disused warships, I reach the welcoming square arches of Noblessner.
This area is called Iglupark, a series of saunas that serve a variety of functions, from food trucks and public bathrooms to, well, actual saunas. I haven’t clocked that it’s the holiday season as I arrive to thumping Christmas songs and families roasting marshmallows on rustic metal campfires. Lonely Planet doesn’t know this is here, yet as I sit on a plastic chair, sipping an ice-cold draft beer beneath a lukewarm ceiling lamp, watching the sea swash as the sensation slips from my cheeks, I realise the truth: it was neither ChatGPT nor Lonely Planet that sparked this story, but my own lust for adventure. Sure, my preference is for a human-written guide over the sprinkles of slop that AI tends to vomit between practical advice. Ultimately, though, the heart of any travel story is the conscious experience of a human being drifting through unfamiliar places.
