Where Travel and Life Intersect

The Cookie-Cutter Trip AI Quietly Sold You

It looks personalized. It’s not. Here is the lens AI sees travel through, and how to push back

You want to plan your next trip. Somewhere new. Somewhere you have wanted to go for years and have not yet figured out how.

You open ChatGPT, Claude, or Gemini and type: two weeks in Uzbekistan.

Ninety seconds later, you have a fourteen-day itinerary. Train times between Tashkent, Samarkand, Bukhara, and Khiva. Visa rules. A photograph of plov so you know what to order. Names of three small hotels on the road to Khiva, where the rooms are clean, and the breakfast is good.

Sounds pretty amazing, right?

Well, unfortunately, the hotel at the top of the list closed last year. The train between Bukhara and Khiva runs three days a week, not seven. The plov in the photograph is from a recipe blog, not from any kitchen in Uzbekistan. And the entire fourteen-day arc is the same arc, the same tool hands the next traveler who types the same prompt.

Beyond the noise

There is a lot of noise about AI right now. Pope Leo XIV recently warned about the technology in his first encyclical, “Magnifica Humanitas.” A Stanford study in Science this spring found that leading AI models are sycophantic, telling users what they want to hear even when the users are wrong.

What you need is something quieter: a working understanding of the lens through which AI sees travel. With that, you can use what AI does well without being at the mercy of what it does poorly.

The lens

The reason your Uzbekistan itinerary came back the way it did is structural. Three things shape what AI returns when you type a travel prompt.

·       Whose voices got fed in. AI is trained mostly on the parts of the English-language internet that have been most clicked and most read. Hotel marketing, TripAdvisor reviews, and the well-known travel blogs. Voices written in other languages, or in small local papers that no algorithm picked up, are weighted lightly or not at all.

·       What is not in the data. The bakery the locals walk to has never been written up. Nor has the bus driver’s shortcut, or the festival the village paper covered once.

·       Who profits from what surfaces. The recommendations that come back are the ones most aggressively optimized to surface: hotels with the largest marketing budgets, restaurants with paid placement on review aggregators, and tours run by companies that know how to play the algorithm.

The cookie-cutter trip

An entire industry is now forming around this. Just as Search Engine Optimization, or SEO, emerged to manipulate where companies appear in Google search results, a parallel industry is taking shape to manipulate where they appear in AI responses. Call it Generative Engine Optimization, or GEO. The recommendations you get from a chatbot today are increasingly shaped by professionals whose job is to make sure their clients are the ones it mentions.

Add it up. Thirty different travelers who type “two weeks in Uzbekistan” into the same tool will get roughly the same answer. The itinerary feels personalized because you typed the prompt yourself. It is not. It is a cookie-cutter trip shaped by the most-clicked-on parts of the internet, and by the people optimizing to surface there. The tool gave you the most-written-about Uzbekistan, not the one a friend would send you to.

What comes next

Knowing this gives you the language to push back. With the right follow-up question, the cookie-cutter trip becomes something closer to yours. The savviest travelers already use the tools this way.

This Dispatch was originally going to cover those tools, too, but it got too long. So we split it. Next week: which AI tools the savviest travelers reach for, with named apps and specific prompts for each.

Destinations worth traveling for — and understanding once you arrive

Mexico City, Mexico: The Mexico City the Algorithm Missed

A case study. We asked an AI for the smart seven-day itinerary. Here is what came back, and what is not in it.

This week’s Chosen Place is a test. We picked one of the most-traveled cities in the Americas, asked an AI for the smart seven-day itinerary, and got back what every traveler gets. It is the cookie-cutter trip we wrote about in the Dispatch. Here are the actual prompt and output.

Prompt: Planning a seven-day trip to Mexico City. Give us a smart itinerary to get an overview and real feel for Mexico City.

Response:

For a smart 7-day Mexico City itinerary that gives you both an overview and a real feel for the city, here’s how I’d structure it:

Day 1: Centro Histórico. Start at the Zócalo, one of the largest public squares in the world. Visit the Catedral Metropolitana and the ruins of the Templo Mayor just behind it. Walk down pedestrian Madero Street, stopping at the stunning Casa de los Azulejos (now a Sanborns restaurant). End the day at the Palacio de Bellas Artes to see the Diego Rivera, Orozco, and Siqueiros murals. Lunch at Café de Tacuba for traditional Mexican cuisine.

Day 2: Chapultepec and Anthropology. Spend the morning at the Museo Nacional de Antropología, one of the best museums in the Western Hemisphere. After lunch, explore Chapultepec Park, including Chapultepec Castle for panoramic city views. Dinner in nearby Polanco.

Day 3: Coyoacán. Take an Uber south to Coyoacán, a bohemian neighborhood with cobblestone streets. Tour the Frida Kahlo Museum (Casa Azul). Book tickets in advance. Walk to the nearby Leon Trotsky House Museum. Explore the colorful Coyoacán Market and Jardín Centenario.

Day 4: Teotihuacán Day Trip. Take a guided tour or Uber to the Pyramids of the Sun and Moon, about an hour outside the city. Climb the pyramids early before the heat. Lunch at La Gruta restaurant inside a cave near the site. Back in the city by late afternoon.

Day 5: Roma and Condesa. Explore these two trendy neighborhoods on foot. Walk through Parque México and Parque España. Stop at boutique shops along Avenida Alvaro Obregón. Lunch at Contramar or Maximo Bistrot. Coffee at Cardinal Casa de Café. Dinner at one of the chef-driven restaurants in the area.

Day 6: Xochimilco and Murals. Spend the morning at Xochimilco, riding the colorful trajinera boats through the canals. Bring snacks and tequila. In the afternoon, visit the Diego Rivera murals at Palacio Nacional and SEP (Secretaría de Educación Pública).

Day 7: Polanco and Final Day. Shop along Avenida Presidente Masaryk. Visit the Museo Soumaya for Carlos Slim’s art collection. Farewell lunch at Pujol (book months in advance) or Quintonil, both ranked among the world’s best restaurants.

Tips: Uber is safe and inexpensive throughout the city. Avoid drinking tap water. The city is at 7,400 feet, so take it easy the first day. The best months are October to May. Spanish helps, but English is widely spoken in tourist areas.

What came back is correct. It is also what every other traveler gets. Here is what is missing.

The day of the week. AI gives you the city as a timeless artifact. It is not. Coyoacán on a Wednesday morning is a neighborhood of cafés and bookstores; on a Saturday, it is a tourist parade. Chapultepec is full of families on Sunday and quiet on Tuesday. Reforma closes to cars on Sunday mornings, six lanes given over to bicycles, joggers, and food carts. Arena México hosts lucha libre on Tuesday and Friday nights. Arena Coliseo runs Saturday shows. Without the day of the week, you get the wrong version of the city.

The cantina hour. Mexico City has a mid-afternoon cantina tradition that AI does not mention. Between two and six, many working professionals stop into cantinas before heading back to the office or home. Each drink comes with botana, small dishes that arrive unprompted and add up to a meal. La Opera near Bellas Artes, La Faena near the Zócalo, and Salón Tenampa in Plaza Garibaldi. None of them is on the AI itinerary. When the writer Michael Parker-Stainback moved to Mexico City in 2007, a local friend gave him one piece of advice, which he later quoted in Saveur: “Be sure to go into every cantina you can.”

Where locals eat. Celebrated restaurants such as Pujol and Quintonil are worth one dinner. The rest of the time, the city eats at fondas and on the street. The comida corrida is the daily institution: a three-course lunch at a neighborhood fonda for what a tourist pays for a coffee at Sanborns. Order al pastor at the right stand, and you understand what tacos are. The right stands have lines of office workers, not lines of foreigners. A traveler who took a local-led food tour wrote this in a review: “The best part was when he took us around a middle-class residential neighborhood full of incredible taquerias, where we got to eat the way locals eat. We would not have been able to find many of those places ourselves.”

The art beyond Frida. AI sends every traveler to Casa Azul. Worth going, but it is a small house with advance-only tickets that sell out days ahead. The Polyforum Cultural Siqueiros, an entire building wrapped in murals by David Alfaro Siqueiros (the muralist who completes the trio with Rivera and Orozco), sits relatively close by and is almost always empty. The Museo Mural Diego Rivera houses one of his finest works, Dream of a Sunday Afternoon in Alameda Park, in its own purpose-built gallery. Neither tends to appear on standard itineraries, and both are worth your time.

Where to actually look. Three places worth a few minutes before you trust any AI itinerary. First, the city’s subreddit. Search r/MexicoCity for “first time,” and you will see what locals tell visitors to skip and what they wish more travelers knew. Second, Substack writers who live where they write. Zoe Mendelson, nine years in CDMX, publishes a guide with the kind of specific knowledge a chatbot cannot reach. Third, a three-hour food or walking tour with a Withlocals or Airbnb-hosted local guide. They will teach you more in an afternoon than any algorithm will in seven days.