The appeal of getting a free, quick, well-structured travel plan is easy to see, and something that is causing travel agents another Covid-sized thing to worry about
Places that don’t exist. Events on the wrong day. Attractions miles apart.
Holiday itineraries designed by AI appear helpful and comprehensive, but are actually riddled with mistakes and old information that could ruin your holiday, analysis of them has found.
More and more people are turning to large language models (LLMs) to plan their trips away. One study puts the number of people who have turned to a bot for holiday inspiration at 40%.
The appeal of getting a free, quick, well-structured travel plan is easy to see, and it’s another Covid-sized thing travel agents have to worry about.
But how good are the robots at the delicate art of holiday planning?
I asked the four biggest LLMs to design weekend break itineries for four destinations, and then called on local experts in those places to assess their work. This is what we found.
Grok
Grok’s London itinerary
Friday
- Settle into your hotel.
- Evening stroll in Covent Garden or Southbank for lights and atmosphere.
- Dinner: Grab classic fish & chips or a pub meal.
Saturday
- 8:30–10:30 Buckingham Palace (Changing of the Guard — check exact time, usually 11am)
- Walk through St James’s Park
- Westminster Abbey** (arrive early to beat crowds)
- House of Parliament & Big Ben** (exterior)
- Cross Westminster Bridge
- London Eye (book a timed slot in advance)
- Walk along Southbank towards Tower Bridge (great photo stops)
- Lunch at Borough Market (if open — excellent food stalls) or Padella (best pasta in London) in Borough
- Tower of London (2–3 hours — see the Crown Jewels early if possible)
- Walk across Tower Bridge
- Sky Garden (free, book slot in advance) for sunset views
- Dinner in Shoreditch or Covent Garden at Dshoom (Indian), Bao or The Palomar (Middle Eastern)
Sunday
- British Museum (opens 10am — focus on Rosetta Stone, Elgin Marbles, Egyptian wing)
- Lunch at Dishoom (King’s Cross or Covent Garden) or Chinatown for variety
- Walk in Hyde Park and Kensington Gardens with afternoon tea at The Orangery
- Covent Garden for street performers and shopping
- West End Show (book in advance — Book of Mormon, Lion King, Wicked, etc.)
Jonnie Fielding, a London tour guide since 2011 with 227,000 followers on Instagram, says the itinerary is “pretty good” if not “generic”, with some glaring issues.
Grok’s suggestions of a walk through Westminster is good, but better if you have a guide point out the smaller details, such as “gas lamps, torch snuffers, fire protection badges”.
The alternative river cruise and London Eye are solid bets for first-timers in the city, but other aspects of the itinerary are less well thought through.
Jonnie argues that the itinerary is far too busy. “I’m a big fan of spending some time people watching. Soaking things in rather than rushing around, and because of the amount in this itinerary, visits to The Tower of London or Westminster Abbey are really rushed,” he said.
The biggest mistake is including the Changing the Guard, which starts at 10:43am at St James’s Palace and doesn’t run on Saturdays.
He concluded: “I know this is a generic itinerary for first-time visitors, but I think London has so much more to offer. Loads of small museums, house museums, places of interest for all interests. They would also leave, not really knowing London.”
Claude
Claude’s Tokyo itinerary
Saturday
Activities
- Tsukiji Outer Market at 8:30am — fresh sushi, grilled scallops, and tamagoyaki from the stallsGet there early; stalls wind down around 1pm
- Sensō-ji temple in Asakusa — Tokyo’s oldest Buddhist temple
- Nakamise shopping street leading up to the temple — snacks and souvenirs
- Tokyo Skytree in the late afternoon to catch the city at golden hour from 450m upBook tickets in advance
- Shibuya Crossing after dark — grab a window seat at the Starbucks overlooking the scramble
Eating
- Tsukiji Outer Market — street eats and fresh sushi at the stalls (breakfast)
- Gyumon Halal Ramen for lunch — wagyu broth simmered six hours, one of the highest-rated ramen spots in TokyoExpect a short queue
- Toridoshi Shibuya for dinner — lively izakaya near the Crossing, great for chicken skewers and drinks
Sunday
Activities
- Meiji Jingu shrine — a forested Shinto sanctuary in the heart of Shibuya, genuinely calming
- Takeshita Street in Harajuku — Tokyo’s wildest pedestrian strip, crepe shops and eccentric fashion
- Shinjuku Gyoen for a picnic lunch — blends Japanese, English, and French garden stylesClosed Mondays and Wednesdays
- teamLab Planets — immersive digital art with glowing flower rooms and a water installationPre-book tickets; sells out regularly
Eating
- Harajuku crepe on Takeshita Street — the classic street food of the area
- NOA Coffee — cosy café nearby with matcha lattes and waffles, good for a sit-down after the crowds
- Sushi Mon Shinjuku for a late lunch before teamLab — affordable, high-quality, order via QR code
Although Claude breaks the itinerary down into activities and eating, offering the reader a little more freedom, its work left Jay Allen from Unseen Japan incredibly cold.
“Overall, this itinerary lacks any context, history, and rich cultural detail that our customers love hearing about on our tours,” Jay says.
The itinerary is full of old information. For example, Tsukiji is no longer the location of a wholesale fish market. It moved to Toyosu several years ago.
“Why did the original market arise in Tsukiji in the first place? None of this rich detail and historic background is included. Even if it were, this info would be drawn from general public sources, not from the rich background that our tour guides – most of whom have degrees in Japanese Studies or years working as journalists in Japan – can provide,” Jay adds.
The Saturday covers little ground and is too geographically spread out, missing “so much rich detail of the Tsukiji/Asakusa shitamachi area”, according to Jay.
Many suggested destinations are “trite”, “well known” or just “commercial”, such as the Starbucks in Shibuya Scramble. “You can get a much better view of the scramble, eg, from the bar at the top of the Magnet building – and you’d be fighting fewer crowds,” Jay notes.
“If you look at the second day, the itinerary gives you no suggestions of cool art galleries and small, uniquely Japan clothing shops to stop (such as the Ura-Harajuku area off the Main Street, where independent fashion still reigns), nor does it tell you about the less-crowded Brahms’ Path that runs alongside the packed Takeshita Street.”
The restaurant recommendations “are the same five places everyone else is going” and are hard to get tables at, as opposed to the real gems that require “a basic working knowledge of Japanese”.
Jay concludes: “Claude is giving you the wisdom of the crowds. That can be helpful in some cases. In this case, it equates to a bland, ordinary vacation that will likely prove an exercise in frustration for most travelers.”
Google AI
Google AI’s New York City itinerary
Friday
- Top of the Rock for panoramic views
- St. Patrick’s Cathedral
- Stroll down Fifth Avenue
- Grand Central Terminal — look up at the ceiling
- Central Park: The Mall and Bethesda Fountain
- Times Square lights
- Broadway show (Check the TKTS booth in Times Square for same-day discount tickets)
Saturday
- The Met or MoMA — pick one and take your time
- Lunch at Chelsea Market
- Walk the elevated High Line park to Hudson Yards
- Dinner in the West Village
- Live jazz at Village Vanguard or Blue Note
Sunday
- Morning ferry to the Statue of Liberty
- Wall Street
- 9/11 Memorial pools
- Walk across the Brooklyn Bridge
- Explore DUMBO for the classic bridge photo
- Giant pastrami sandwich at Katz’s Deli
- Speakeasy drinks at Attaboy or PDT
Amy Siegal, a luxury travel advisor based in NYC, praised Google AI for highlighting some “iconic spots”, but argued that only “a human expert knows the ins and outs of these places – what time of day to go where, and in which order they’d work best.”
On day one, Amy suggests arriving at TKTS earlier in the day to have more choice of shows and seats, and to avoid the line.
Saturday’s itinerary has too much “darting around”. She suggests it could be arranged more smoothly, with more interesting food options chosen.
Sunday is packed full of landmarks and history, which is good, but the order is wrong. “I would incorporate some lesser-known landmarks and eateries,” Amy added.
ChatGPT
ChatGPT’s Algarve itinerary
Friday
- Check into your accommodation in Albufeira
- Wander through Albufeira Old Town — whitewashed buildings, cobbled streets and ocean views
- Stop for a drink at a terrace bar overlooking the beach
- Head to Praia dos Pescadores to watch the sunset
- Dinner at a traditional Portuguese restaurant — try grilled sea bass, octopus salad or cataplana
- Cocktails in the Old Town, or head to the Marina for a more relaxed atmosphere
Saturday
- Drive early to Benagil
- Book a boat tour, kayak or paddleboard trip to the famous Benagil Cave
- Spend time at Praia da Marinha, one of Europe’s most beautiful beaches
- Lunch overlooking the coast — grilled sardines, fresh seafood and Portuguese wine
- Walk part of the Seven Hanging Valleys Trail for clifftop views over hidden coves and sea arches
- Alternatively, relax on the beach
- Sunset drinks in Carvoeiro overlooking the sea
- Dinner in town before returning to Albufeira
- Head out for nightlife — Saturday is the busiest night of the week
Sunday
- Drive west to Lagos
- Explore the historic town centre
- Visit Ponta da Piedade — walk the cliff paths or take a boat trip through the sea caves
- Lunch at Lagos marina or in the old town
- Spend your final few hours at Praia do Camilo or Meia Praia
- If your flight is later, stop at Sagres for Atlantic views and a visit to the historic fortress
Vicky Reeves, who is the director of The Real Algarve villa company, applauded ChatGPT for picking out some “amazing places” in its “very good overview,” but argued it failed to consider flow, how much is possible to fit in, and the weather.
“Understanding seasonality is important because this itinerary would feel very different in August compared to November and that is something an agent or guide would pick up on. I also think it’s a bit ambitious and that’s really down to a lack of practical knowledge and insight,” Vicky explained.
“For example, the plan suggests exploring Lagos, visiting Ponta da Piedade and potentially heading to Sagres before flying home. That’s fine if you’ve got a late return flight, but an agent or guide would check to make sure that everything was possible without adding stress or risking your flight home. Benagil is also another good example. It’s one of the Algarve’s most iconic attractions, but during peak season, travel times and parking can be difficult, and tours often need booking well in advance, which isn’t really considered at all.
“The AI did pick out some amazing places, but I do think it’s missing a personal feel. It doesn’t suggest any hidden beaches or lesser-known spots because that’s much harder for AI to uncover. That insight can really make all the difference in making a trip feel unique.”
In conclusion
What is most striking about the itineraries is how comprehensive and well thought out they seem – particularly Claude’s – but how riddled with issues they are once a closer look has been taken.
ChatGPT suggesting an event that doesn’t take place on the requested day is a rookie mistake that could disrupt a trip, while Claude not realising a famous fish market has moved is similarly clumsy.
All the AIs seem too ambitious when it comes to the number of activities and the distance between each.
Certainly, the bots are great if you’re looking for a broad overview of a place, but they lack the precision you’d want to fully rely on its suggestions, and the depth of knowledge a local guide can provide that can bring a place to life.

