AI Adventures Gone Wild: Local Discovery Bot Leads Reporters on Unforgettable Urban Escapades

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We Requested AI to Guide Us Through Our Urban Landscapes. It Turned into Mayhem

Eager to uncover some undiscovered treasures within our own cities and armed with $100 (£77) each ready to be spent, we—Natasha Bernal in London and Amanda Hoover in New York—turned to AI to craft the ideal day for us.

We opted for Littlefoot, a chatbot equipped with AI designed for uncovering new local adventures, capable of crafting experiences across 161 global cities. This innovative tool is the brainchild of Bigfoot, a venture initiated by ex-Airbnb leaders Alex Ward, James Robinson, and Shane Lykins. Their vision was to integrate the intelligence of every accessible public AI chatbot, including notable names like ChatGPT, Claude, Llama, Anthropic, and Perplexity, along with insights from 50 different data sources, including Tripadvisor and Google. Bigfoot utilizes a trio of distinct language models acting as "AI agents" to assemble travel itineraries.

We shared with Littlefoot where we were each starting from, when we were beginning, and the specific times, while also presenting some conditions: Amanda requested her New York journey to accommodate dogs; Natasha insisted on steering clear of the bustling tourist areas in London.

The outcomes were quite astonishing. Presently, Littlefoot seems to lack any understanding of temporal or spatial awareness, or what might captivate a human interest. Its suggestions oscillate greatly, ranging from highly specific activities (like ascending a hill in South East London), to extremely broad ideas (such as a visit to the London Zoo without any additional details). The same few attractions — including the London Eye, the Namco Funscape arcade in Romford, and a cycling studio in Brooklyn — repeatedly appeared in its suggestions, raising suspicions of potential paid advertising. However, Bigfoot has clarified that this is not the case and it does not intend to introduce sponsored recommendations.

The platform suggested consecutive gym appointments in London, followed by a concert and helicopter ride in New York which were beyond our financial reach, dining options for lunch that weren't available until the evening, and plans that would result in unnecessary travel across our cities. In London, the mapping feature of Bigfoot inaccurately displayed two of the four recommended places, a problem that the firm acknowledges and is addressing.

"Anticipating the usual obstacles that come with being a nascent enterprise, we remain optimistic about overcoming these as we gain additional resources and further tailor our strategy with insights from our users," stated Alex Ward, CEO of Bigfoot. "As a preseed startup with a team of six, we understand that our plans won’t be flawless at this stage. However, we are committed to making all necessary efforts to achieve our goals soon."

Bigfoot mentions that its capabilities, heavily dependent on the user's input location and the way requests are formulated, have undergone trials by 70 to 80 early adopters this year, with the firm making adjustments to the platform in response to their suggestions.

Exploring London's Queen Elizabeth Olympic Park for a Day

I chose to spend my day exploring the 560-acre sports complex, complete with pedal boats, a velodrome, and tennis facilities. It was my first visit, and I was expecting an enjoyable experience. Unfortunately, it fell short of my expectations.

I began my day at 10 in the morning at the WIRED office located in the heart of London. Our initial destination was in the eastern part of the city, aiming for a meal at Pizza Union. However, we discovered it didn't open until 11, and contrary to what Littlefoot had mentioned, the slices weren't priced at £6. Equipped with Google and accompanied by my colleague at WIRED, Sophie Johal, who's also from London, we set off on a journey via the underground, covering a distance of 3 miles to reach Aldgate East—a place I'm pretty sure no one visits out of their own free will.

We waited around until it was time for the pizzeria to start serving. I opted for a margarita pizza and a water bottle, then we took our seats on a wooden bench by the pavement, which offered a glimpse of a strip joint named White’s. I coughed slightly when a particularly crunchy basil leaf caught me off guard.

Subsequently, we traversed slightly more than a mile to our following destination, the venerable Borough food market, situated in the vicinity of London Bridge. En route, nestled under the entryway of the 17th-century Saint Magnus the Martyr church, we stumbled upon an ancient, 2,000-year-old wooden log, appearing quite weathered and aged. Had it not been for our journey, it's conceivable that we would have gone through our entire lives without ever encountering it.

Crossing over the London Bridge, we made our way to the marketplace, maneuvering through crowds adorned with bags and various barriers, until we stumbled upon Horn OK Please. This serendipitous find turned out to be one of the few vegetarian options available. Positioned beside a garbage can, we indulged in a midday snack of dosa chaat, a savory crepe stuffed with spiced potatoes, onions, cilantro, and a mix of chutneys. Overcome by the heat and feeling overwhelmingly full, I began to doubt my ability to reach the Olympic Village.

We hopped back onto the subway and took a roundabout route to Trafalgar Square—located 2 miles distant and a mere five minutes from the WIRED headquarters. We found ourselves waiting in a packed line for 10 minutes outside the National Gallery, and following a tour of well-known artworks by artists such as Degas, Murillo, Raphael, and Gainsborough, we indulged in some souvenirs from the gift shop (including pins adorned with Van Gogh and Manet pieces and the museum's emblem, along with a chocolate coin—the only items that fit our budget).

Hopping back onto the subway, I experienced the Elizabeth Line for the first time since its opening in 2022, en route to Stratford and the Olympic Park. Exhausted and parched, I guided us past the colossal Westfield shopping center, which was adjacent to an enormous parking lot, towards a path that was less than picturesque, nestled among apartment buildings. It was by then we had realized our plans were thwarted: the pedal boats were out of service, the cycling track required a pre-participation training session, and renting the tennis courts was beyond what our dwindling budget could afford.

The grotesque steel Orbit Tower was nowhere in sight, nor was there anything else of significance—our view was merely composed of rows of medium-height apartment buildings and a sizable green space. Inspired by the Olympic atmosphere and capitalizing on the absence of a crowd, we endeavored to tackle an obstacle course at an adjacent outdoor gym. (We found ourselves entangled in the apparatus on several occasions.)

That’s the story of how we found ourselves disoriented near the Wetlands Walk by the River Lea, pedaling on the sole e-bike for rent I was able to locate. Regrettably, it was programmed to move at an alarmingly fast pace, leading me to yell out in real terror for roughly 20 minutes as I zoomed repeatedly across the same patch of foul-smelling marshland, while Sophie clung to the mudguard in a manner reminiscent of a makeshift saddlebag.

After the rain started coming down hard, I decided to stop trying to look for a destination, having already spent £6 on an e-bike that ended up taking me on a fruitless journey. We didn't manage to locate the bike path and felt too worn out to make it to Bradley’s Spanish Bar, which was six miles away. I opted for an ice cream instead (choosing two flavors: stracciatella and chocolate hazelnut) at a shop close to the train station. Following that, I enjoyed a cup of tea and, with £64 spent in total, I decided to wrap up the day.

During the bleakest times, I might have characterized the schedule as slightly malevolent and mostly futile. A mere two minutes online could yield a more coherent strategy, yet it wouldn't match the unpredictable and haphazard nature that made it so memorably unique.

Immediately upon returning home, I sought ChatGPT's advice for an alternative outing. It proposed an explorative journey through South Bank, meandering past landmarks such as Big Ben and the London Eye, and incorporating pauses to appreciate various artistic and cultural highlights. This idea seemed logical, yet a tiny segment of my being—the portion that squealed with excitement upon discovering a massive slide we could use—pondered if there might be an enchanting quality to Littlefoot's ordinary (and seemingly silly) suggestions.

Exploring Washington Square Park and Central Park in New York with a Pooch

I was curious to find out if Littlefoot could tackle a slightly difficult task: organizing a day in Manhattan that would be suitable for my dog, Charlie, a 22-pound poodle mix, to join. Unfortunately, it wasn't up to the task.

The application suggested a park in New Jersey that could only be reached by car, along with two eateries featuring the term "dog" in their names—though it's doubtful that dogs would be permitted entry—and consistently nudged me towards attending a spin class in Brooklyn, likely due to the inclusion of the term “friendly” in its summary. It also pointed out a costly helicopter ride around Manhattan as an option for outdoor adventures, and at a certain juncture, recommended a Noah Kahan performance (which was sold out, leaving only expensive tickets up for resale).

Exploring the selections required effort and multiple attempts. Quite a few of the eateries Littlefoot pointed out weren't open during the recommended visit times, and the suggestions often involved traveling across different urban districts, or sometimes even more distant locations—even when my request was specifically for a Manhattan itinerary that could be easily navigated via the subway system.

I merged and trimmed two travel plans to avoid the pain of spending numerous hours on the subway. Departing from Harlem at about 8 in the morning, I made my way to my initial destination: the Obelisk in Central Park, an ancient monument that's 3,500 years old and was transported from Egypt. Charlie was especially pleased with this arrangement, since we arrived at the park when dogs were allowed off their leashes, giving him the freedom to explore the park's green spaces and paths alongside other dogs.

We trekked for a mile through the Upper East Side of Manhattan to reach Claire's Kitchen Cafe, a quaint little place with a Mediterranean flair and outside dining, suggested by Littlefoot. It was clearly a local favorite, not aimed at tourists. I enjoyed a breakfast sandwich with cream cheese and smoked salmon, along with a latte. Both were tasty, though not exceptionally so to warrant a special trip to another area.

Charlie and I hopped on the subway and headed towards the downtown area, disembarking close to Washington Square Park, which was our planned destination. The park seemed more peaceful than usual for a weekday morning, though it appeared there were likely TikTok users approaching individuals sitting on benches for impromptu interviews. We strolled beyond the famous arch and fountain, eventually pausing at the dog park, where I enjoyed tossing a tennis ball for Charlie to chase.

We returned to the subway and traveled to the 9/11 Memorial & Museum, a solemn destination suggested by AI among other recommendations for parks and bars. Since I had my dog with me, entering the museum wasn't an option, but we took a stroll around the memorial where Charlie gained some popularity among the visitors.

The final destination on our journey was the Dead Rabbit, a unique Irish tavern we stopped at for lunch. This spot is renowned for its high-quality pub grub and cocktails, featuring shelves adorned with dollar bills. It's acclaimed by many as the world's top bar, and to our fortune, it welcomed pets. There was one small table available outside upon our arrival. My meal consisted of a burger and a beverage, costing around $50 including gratuity. (During our meal, Charlie dozed off by my feet, unfazed by the construction noise in the vicinity, thoroughly asleep.)

Roughly five hours into the journey, I found myself both tired and $90 poorer, a sum that had gone towards subway fares and meals. Our trek had us journeying from Harlem, situated at Manhattan's northern end, all the way down to the Financial District at its southern tip. This excursion involved boarding five different trains and covering a distance of 5 miles on foot in order to visit the locations suggested by Littlefoot. To navigate through these recommendations efficiently, I had to draw upon my personal understanding of the city's layout.

Later, I put a similar query into Perplexity's chatbot and obtained an itinerary that included more information on costs and transportation options. However, this attempt was also flawed. It suggested bringing Charlie to the famous High Line in Manhattan, where dogs are not permitted, and offered unclear suggestions on purchasing a bagel from a street vendor "close to" Central Park. Nonetheless, it provided suggestions for various well-known city areas that would allow me to stay within my budget.

Littlefoot inspired me to visit new eateries and discover hidden gems within well-known parks, providing a much-needed break from my usual daily activities. However, if I had strictly adhered to its suggestions, I could have found myself in Brooklyn or Queens in front of shut restaurant doors, or overspending on certain activities. While AI offers innovative ideas, until it becomes more reliable, I prefer getting advice on where to go from another New Yorker.

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