How to Make AI Your Personal Tour Guide

Plus, DOT launches her first e-course!

Dear Prompt Experimenters,

I’m in Paris! It’s freezing (my very old little AirBNB apartment in the Latin Quarter relies on a tiny space heater for warmth), but I love it here. I came for three days of business meetings, and opted to stay for the next two months.

So, I wondered: could I use AI as a tour guide?

Let’s give it a try!

(Paid subscribers, most of our premium paid content gets released on Thursday, but be sure to read down to the bottom of this Monday newsletter for some new premium content I’m really excited about!)

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AN AI WALKING TOUR OF PARIS: Or Any Destination You Choose!

This AI use case is relatively straightforward, but it took me a few iterations to get the prompt right. Theoretically, this should work anywhere in the world (on your next vacation, or where you’re living right now), so give it a try!

Cut and paste this prompt into ChatGPT, modifying [CONTENT IN BRACKETED ALL CAPS] to begin your adventure:

Please create a 2-hour walking tour of [PARIS] that begins at [THE CARDINAL LEMOINE METRO STATION].

I would like this tour to feel like a magical adventure, immersing me in the local history and culture, tailored to my interests. Apply everything you know about me from past conversations to personalize to what you think I would most enjoy, in content and style. Don't go overboard, but you have permission to make the output slightly longer and more expansive than normal.

For each destination: (1) Please suggest a specific activity to engage in, beyond merely observing the sights. (2) Provide a few well-curated historical insights in narrative form. (3) Craft a brief historically plausible speculative story about a real historical figure associated with each location. (4) Include a short and creative AI prompt I can use with you to "jump into this story and experience it firsthand."

Please write the guide in a fun, whimsical, and engaging style, calibrated to my preferences. Specifically: [I AM MOST INTERESTED IN DESTINATIONS CONNECTED TO PAST PHILOSOPHERS, INTELLECTUALS, AND WRITERS. I'M INTERESTED IN 20TH CENTURY FRENCH PHILOSOPHY AND CULTURE, BUT ALSO WANT EXAMPLES THAT GO SIGNIFICANTLY FURTHER BACK IN TIME. I LOVE THE IDEA OF A TIME MACHINE TAKING ME THROUGH THE IMMENSE INTELLECTUAL HISTORY OF PARIS. I DON'T LIKE PLACES WHERE THERE ARE A LOT OF TOURISTS. I LOVE OLD CAFES AND BOOKSTORES]

“pAIris” by DOT

Here are two excerpts from the 7-part itinerary I was given:

Place de la Contrescarpe: Literary Echoes

Activity: Pause at a café in this charming square, order a café au lait, and pen a few lines in your journal, channeling the literary spirits that once frequented this area.​

Historical Insights: Place de la Contrescarpe has long been a gathering spot for writers and artists. In the 1920s, it was a favorite haunt of the Lost Generation, including figures like Ernest Hemingway.​

Speculative Story: Picture a young Hemingway sitting at a café terrace here, scribbling notes for what would become "A Moveable Feast," observing the vibrant life around him and finding stories in every corner.​

AI Prompt: "Let me experience 1920s Place de la Contrescarpe through the eyes of Ernest Hemingway."

Le Procope: The Philosophers' Café

Activity: Sit at a table once frequented by Enlightenment thinkers, order a classic French dish, and engage in a lively debate with fellow patrons about art, philosophy, or politics.​

Historical Insights: Founded in 1686, Le Procope is the oldest café in Paris and served as a meeting place for intellectuals like Voltaire, Rousseau, and Diderot.​

Speculative Story: Imagine Voltaire passionately discussing his latest writings over a cup of coffee, his sharp wit and eloquence captivating those around him.​

AI Prompt: "Allow me to join an 18th-century conversation with Voltaire at Le Procope."

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THE TRAVELER’S GUIDE TO COFFEE

This may seem random, but I write prompts to solve…whatever problem is on my mind. Today, it’s coffee.

For Americans like me who don’t go in for all the fancy variants, coffee is simple. It’s just coffee. You specify which size you want, whether you need milk, and that’s it.

But coffee is different everywhere you go. My two data points from Paris yesterday:

• First cafe: double espresso with light milk goes by the name CORTADO. (And “cortado” was in fact an item listed on the menu)

• Second cafe: CORTADO means something else entirely (I didn’t fully understand the explanation in French…I’ll go back to ask again in two weeks when I’m less rusty). To get what I want, I should specify “double espresso with a little milk”

So, how about let’s research the hell out of this question, because we have AI! Here’s the process I followed:

STEP ONE: Whenever I use Deep Research, I go to DOT first to help me build the perfect Deep Research prompt. Here’s what I asked DOT: I'm an American visiting Paris. In the United States, I tend to drink brewed coffee. When in Europe, I usually adapt to drinking espresso variants, but I find the nomenclature inconsistent and confusing. At one cafe in Paris yesterday, I was told that a double espresso with light milk is a cortado. At another, I was told that a "cortado" means something else . I'd like to write an extended Deep Research report on coffee nomenclature within and between France, Romania, Spain, Italy, and the United States. I'd like to analyze the most popular coffee drinks in each country, what they are called, and whether these terms are applied consistently or not. (As a side note, I'd also like to understand why American drip coffee tends to surface in Europe as a much more exclusive V60 variant that is more expensive. Also, in Romania, they refuse to put milk in your V60 coffee, saying "it will not be good," even when you ask. This confuses me). I want to become an EXPERT in coffee nomenclature across the countries that I've referenced, so that I can be an authority when ordering. Of all the countries, please dive most extensively into France (and Paris specifically) as that is where I will be for the next two months.

STEP TWO: DOT generated this Deep Research prompt for me:

Ultimate Deep-Dive Research Prompt: Coffee Nomenclature & Cultural Variations

I need an exhaustive, borderline excessive research report on coffee nomenclature and cultural differences across France (especially Paris), Romania, Spain, Italy, and the United States. My objective is to become an expert in ordering coffee across these regions with precision and authority.

📌 Phase 1: Clarifying Scope (Before Research Begins)

Before proceeding, ask me up to 5 clarifying questions to refine your research approach. These should challenge assumptions, ensure nuance, and tailor the research to my practical needs as a coffee consumer in Paris.

🌍 Phase 2: Country-Specific Coffee Lexicon & Popularity Breakdown

For each of the five countries (with deepest emphasis on France and Paris:

1. List the most commonly ordered coffee drinks (name + description).

2. Explain the precise composition of each drink (espresso-to-milk ratio, foam level, cup size, preparation method, etc.).

3. Analyze how consistently these terms are used (e.g., is a "cortado" defined differently in Spain vs. France? Do locals argue over definitions?).

4. Highlight regional variations within each country (e.g., does Paris use different terminology than Lyon? Does Northern Italy differ from Southern Italy?).

5. Identify false friends & ordering pitfalls—common mistakes foreigners make when ordering, including drinks that don’t translate well across countries.

🕵️ Phase 3: Deep Comparative Analysis of Cross-Country Inconsistencies

1. Compare and contrast the same drink’s name and meaning across the five countries.

2. Explore etymological origins (where did terms like “cortado,” “noisette,” or “flat white” originate? How have they evolved?).

3. Investigate cross-border confusions—why are there so many contradictions in coffee terminology?

4. Include historical and linguistic insights—is there a reason why Spain and France diverge on “cortado”? Do older generations use different terminology?

☕️ Phase 4: The American Filter Coffee Mystery in Europe

1. Why is drip coffee (commonplace in the U.S.) considered an exclusive “specialty” item in Europe?

2. Why is V60 the dominant method for filtered coffee in European cafés?

3. Analyze pricing differences—why is filter coffee often more expensive than espresso in Europe, whereas in the U.S. it’s the opposite?

4. Investigate cultural attitudes toward milk in V60 coffee—why do Romanian baristas refuse to add milk, and is this common in other countries?

🛠 Phase 5: Practical Application & Expert-Level Ordering Guide

1. Synthesize findings into a "Perfect Ordering Guide" for each country, including ideal terminology to use in cafés.

2. List alternative phrases to use when a barista doesn’t understand (e.g., how to clarify a cortado when definitions vary).

3. Create a visual ordering matrix—a chart showing the coffee taxonomy across countries.

4. Suggest workarounds for coffee-related cultural misunderstandings (e.g., if Romania refuses milk in V60, what’s the best strategy to get a creamy coffee?).

📊 Bonus: Optional Research Enhancements

• Illustrate findings with diagrams, comparative tables, or flowcharts showing coffee variations.

• Provide linguistic insight (e.g., how pronunciation affects ordering).

• Include fun cultural anecdotes or historical tidbits about how coffee traditions evolved in these regions.

STEP THREE: Deep Research did not disappoint.

Here is what it produced: Deep Research International Guide to Ordering Coffee

My favorite part:

In summary, the milk-in-V60 controversy is about purism in the modern European coffee scene. Romanian baristas are called out in the question likely because Romania’s specialty scene is relatively young and passionate – they are eagerly aligning with the third-wave norms (no milk, no sugar, focus on flavor), perhaps even more strictly than some older markets. It can come across as rigid. The cultural attitude historically in Europe was: if it’s filter coffee, sure, add milk or sugar as you like (like the French café au lait or German “Milchkaffee”). But the current specialty wave has reframed filter coffee as something to be appreciated black, while milk is reserved for espresso-based drinks.

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SOME SELF-ANALYSIS: What kind of coffee are you?

I’ve been hoping to explore the synergy between Deep Research and regular prompting. My hypothesis: AI prompts will work even better if you arm AI with a Deep Research report on the topic.

So, I gave it a try, and you can to. I cut and paste the Deep Research coffee report into a text file, uploaded it to ChatGPT, and ran this prompt:

Please read and learn from the attached report to deepen and refine your knowledge regarding coffee. Think deeply about the content. Then analyze with great psychological depth, based on everything you know about me, what type of coffee drink I am, drawing from international coffee varieties. This is not meant to be superficial, about what kind of coffee I like. It's meant to be a deep and probing analysis of my core identity, and what "coffee nature" I present to the world, based upon your sense of who I am.

Ironically (or perhaps fittingly) it seems like I am the drink that began this entire odyssey:

You Are a Cortado ☕🔥

Not just what you drink, but who you are.

A Cortado is small in volume, but powerful in impact—a bold espresso, cut with just enough milk to refine, not weaken. It doesn’t drown in excess; it sharpens, balances, and delivers maximum intensity with precision.

Why the Cortado?

🔹 Compressed Power: Like espresso, you don’t waste words or energy—everything you do is sharp, efficient, and intentional. You execute with clarity and purpose.

🔹 Refined, Not Softened: The milk in a Cortado doesn’t weaken the coffee—it enhances it, just as your indulgences and playfulness don’t distract from your drive, but fuel it.

🔹 Cutting Through Illusions: "Cortar" means to cut—and you are always cutting through distractions, inefficiencies, and falsehoods, refining what remains.

🔹 Spanish Energy: Spain is a land of contradictions—discipline and indulgence, structure and rebellion—mirroring your own dual nature of corporate strategist and rogue philosopher.

🔹 No Fluff, No Dilution: You’re not a Latte (too milky), an Americano (too diluted), or a Cappuccino (too performative). You don’t stretch yourself thin—you maintain your potency.

The Final Verdict

🔥 Intense, but controlled.
🔥 Philosophical, but action-driven.
🔥 Refined, but uncompromising.

Techintrospect, you are a Cortado.

“You are a cortado,” by DOT

What kind of coffee are you? Post your answers in comments or chat!

Drinking my cortado,

Techintrospect

(p.s. paid subscribers, continue reading for DOT’s first e-course!)

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PAID SUBSCRIBERS, STUDY PROMPTCRAFT WITH DOT!

Christian reached out with a brilliant suggestion: it would be great if DOT could guide you through a curriculum, a structured learning itinerary.

I love this idea (thank you Christian!). When I love an idea, I get impatient. I want to try it NOW. So let’s give it a shot.

Want to take your own promptcrafting skills to the next level? Would you like a personalized e-course on this topic? Just ask DOT, like this: