Over the past few months, I’ve written about frustrations with travel planning online. The volume of ads makes pages unreadable, the AI slop is overwhelming, and, unfortunately, many great travel bloggers have stopped blogging since the revenue incentive has pretty much disappeared and they have had to get proper jobs.
Another of these was related to my day job: agentic travel planning isn’t quite ready for prime time. AI can certainly assemble an itinerary, but it often optimizes for what most tourists want instead of what you actually enjoy. It happily sends everyone to the same “Top 10” attractions, the busiest restaurants, and the most photographed viewpoints.
The second realization was more personal. As I’ve gotten older, my desire to travel hasn’t disappeared but has become much more selective. I no longer travel to collect countries or rush through attractions. I travel to understand places, wander neighborhoods, photograph interesting architecture, visit museums, discover local food, and experience how people actually live. On top of that, my patience for wading through all the crap I mentioned previously.
Those two ideas led me to change how I use AI.
Instead of asking, “Plan my trip to Germany,” I spend a few minutes teaching AI who I am as a traveler. That small change makes an enormous difference.
Once the AI system understands what you enjoy, what you avoid, your pace of travel, transportation preferences, budget, photography interests, mobility considerations, and even the kinds of restaurants you dislike, every recommendation becomes dramatically more relevant. Rather than replacing travel research, AI becomes an intelligent research assistant that filters thousands of possibilities through your personal preferences.
I’ve found this approach works far better than expecting an AI agent to magically build the perfect itinerary. It gives you control while still taking advantage of AI’s ability to organize information, compare options, and uncover places you might never have discovered on your own.
When my daughter recently began planning a trip to Germany, I put together the collection of prompts below. Many of these are the same prompts I use myself before almost every international trip. They aren’t designed to eliminate the joy of discovery. They’re designed to help you spend less time sorting through generic recommendations and more time discovering experiences that actually match the way you like to travel.
If you’ve been disappointed by generic AI travel itineraries, start here. Don’t ask AI where to go first.
Teach it who you are.
Best Prompts for Trip Planning
Planning a trip to a foreign city is much easier and more personal when you use targeted, customizable prompts to guide your research. Below are some of the most effective prompts, organized by category, that you can use to uncover local gems, practical advice, and memorable experiences.
For best results, personalize these prompts by specifying your travel dates, unique interests, the number of people, your budget, and any particular questions or concerns. The more details you provide, the more tailored and insightful your travel research will be.
Personalize Your Trip Planning: The “About Me” Travel Prompt
A highly effective way to kick off your travel research is by creating a personalized “About Me” travel prompt. This sets the foundation for tailored recommendations, helping you (and any tools you use) instantly focus on what will make your trip memorable and comfortable. For best results, personalize these prompts by specifying your travel dates, unique interests, the number of people, your budget, and any particular questions or concerns. The more details you provide, the more tailored and insightful your travel research will be.
Note: For my upcoming Romania trip, when I added the dates I would be there, it immediately changed the recommendation because two of the locations I stated I wanted to visit were closed on Mondays, so it recommended I switch my Sunday and Monday plans. Two of the potential tour operators for the Monday tours did not have notices that the castles were closed. A third one had a note that on Mondays you cannot enter the castles.
What to Include in Your “About Me” Travel Prompt
- Interests & Hobbies: What do you enjoy doing while traveling? (e.g., art museums, hiking, vintage shopping, live music, local history)
- Preferred Activities: List the types of experiences you seek (and those you prefer to avoid). (e.g., guided tours vs. solo exploration, nightlife, group activities, adrenaline sports)
- Activities to Avoid: Experiences or environments you’d rather skip (e.g., extreme sports, nightlife, crowded tourist spots, long guided tours, shopping malls, or certain weather conditions).
- Mode of Transportation: Your ideal ways of getting around. (e.g., public transport, taxis, walking, bike/scooter rentals)
- Favorite Food Experiences: Culinary Interests and Dietary Needs. (e.g., street food, fine dining, vegetarian/vegan options, cooking classes, specific cuisines)
- Climate & Temperature Preferences: What weather do you thrive in? (e.g., warm and sunny, cool and crisp, able to handle rain/snow)
- Mobility Considerations: Any accessibility needs or physical restrictions, from step-free access to stamina for walking.
- Sub-Focus or Travel Goals: What’s your deeper aim? (e.g., immersing in local culture, discovering hidden gems, capturing Instagram-worthy photos, relaxation, personal growth)
- Photo & Social Media Preferences: Are you looking to document your trip for social media or simply enjoy the moment?
Example “About Me” Travel Prompt
“I love exploring vibrant neighborhoods, street art, and local food markets. I avoid large crowds, extreme sports, and nightlife. I prefer to walk as much as possible and use public transit for longer distances. My favorite food experiences involve local street foods and local cuisine. I enjoy mild, sunny weather and have no mobility issues. My main travel goal is to get lost in authentic culture and take great photos for my blog, especially of unique architecture and cultural differences.”
Starting your research with a personalized prompt like this ensures your trip planning is highly customized, giving you the best chance to discover what you value most, while easily filtering out less relevant options.
If you have even more specific preferences, you can add an Avoids prompt.
What to Include in Your “Avoid” Travel Prompt
Adding a more extensive “avoids” prompt list, not just to activities, but also to settings, transit, seasons, social, and sensory preferences, will help ensure a smoother, more enjoyable adventure that matches your unique needs. By specifically listing the activities you want to avoid, you further streamline your search and ensure your itinerary only includes experiences that fit your style and comfort level. This approach helps you focus time and energy on what truly matters during your journey.
Sample “Avoids” Travel Prompt
“Please avoid recommending activities or settings that involve large crowds, overly touristy attractions, noisy environments, or places that require long or complicated transit transfers. I’d also like to skip activities centered on nightlife, extreme sports, shopping malls, or rigid group tours. I prefer not to visit destinations with excessive heat, humidity, or allergy-inducing weather, and I’d like to avoid restaurants specializing in spicy foods or those with poor hygiene. I do not enjoy animal-based tourism, strenuous hikes, or environments with intense sensory stimuli (such as bright lights or loud music). Please only suggest experiences that align with these preferences.”
General City Research & Itinerary Planning
Once you have identified your preferences, you can begin exploring the perfect trip and activities.
- “Create a [number of days]-day itinerary for [city] focusing on [interest, e.g. food, history, art, family activities]. Assume I’m traveling as [solo, couple, family].”
- “What are the top 5 must-see sights and 3 unique, lesser-known experiences in [city]?”
- “Suggest a walking tour route for [city] including both iconic landmarks and authentic local spots.”
- “Design a themed day itinerary in [city] for someone interested in [theme: such as street art, literary history, local food].”
- “I have [number] days in [city]. What is the best way to balance major attractions and hidden gems?”
2. Food, Drink, and Local Culture
- “Where do locals eat in [city]? List three highly recommended but non-touristy places for [specific cuisine or dish].”
- “What do bloggers in [language or country] recommend. (my Porto experience)
- “What local markets or food halls should I not miss in [city]? What special foods or souvenirs can I find there?”
- “Are there any notable festivals or cultural events happening in [city] between [dates]?”
3. Neighborhood and Accommodation Guidance
- “What are the safest and most vibrant neighborhoods for visitors in [city]? Suggest areas for different budgets.”
- “Recommend unique or boutique hotels or Airbnb stays in [city] in quiet but central neighborhoods.”
- “What public transport options are best for getting around [city]? Compare metro, buses, taxis, and bike shares.”
4. Customization for Interests and Travelers
- “I love [interest: e.g. modern art, hiking, vintage shops, live music]. What experiences in [city] align with my interests?”
- “Suggest off-the-beaten-path activities in [city] that would surprise a repeat visitor.”
- “List some workshops or local classes (like cooking, crafts, language lessons) suitable for travelers in [city].”
5. Practical Tips & Logistics
- “What should I pack for a [season] trip to [city], considering weather and local customs?”
- “Summarize important customs and etiquette for visitors to [city]. Are there any major faux pas to avoid?”
- “How does tipping work in [city], and what are average prices for dining, taxis, and attractions?”
- “What is the best mobile connectivity option (SIM card, eSIM, Wi-Fi) for tourists in [city] for a [length of stay] trip?”
6. Budgeting, Safety, and Travel Hacks
- “What’s a reasonable daily budget for a [type of traveler] in [city], including meals, transit, and entry fees?”
- “Are there free or discounted days for museums and attractions in [city]?”
- “What are the top safety tips for visiting [city], especially for solo travelers?”
7. Decision-Making & Comparisons
- “I’m deciding between [city A] and [city B] for a [number of days] trip. What are the key differences in culture, costs, and highlights?”
- “Summarize the main pros and cons of visiting [city] in [season/month] versus other times of year.”
Tip: For best results, personalize these prompts by specifying travel dates, interests, travel companions, budget, and particular questions or concerns. The more details you provide, the more tailored and insightful your travel research will be.
Sample Travel Prompt for Exploring Multiple Cities by Train
If you want to receive tailored recommendations for a multi-city train journey, your personalized “About Me” prompt might look like this:
“I want to explore several cities in [country] by train. I enjoy discovering vibrant neighborhoods, local cuisine, historical sites, and scenic routes. My preferred pace is relaxed, with time to wander and take in local culture. I’d like to avoid activities set in crowded, overly touristy locations and experiences that require long bus transfers or restrictive guided tours. I prefer walking or using public transport within cities. My ideal food experiences focus on authentic local specialties, markets, and cafes rather than fine dining. I enjoy mild, comfortable weather and prefer to skip cities or regions with extreme temperatures.”
Additional Details to Include for Even Better Results
- List of Preferred Cities or Regions: “I’m most interested in visiting [City A], [City B], and [City C], but open to others along the train route.”
- Time Frame and Trip Duration: “I have [X] days and will be traveling in [month/season].”
- Interests & Activities: “Please recommend museums, local markets, walking tours, and any not-to-be-missed cultural events.”
- Scenic Train Experiences: “Suggest train routes known for beautiful landscapes or historical significance.”
- Accessibility or Comfort Considerations: “I prefer reasonable daily travel times (under 4 hours per day) and would like advice on comfortable train classes or sleeper cars if overnight journeys are suggested.”
- Food Preferences/Restrictions: “I am a vegetarian and would appreciate recommendations for train-friendly meals and restaurants in each city.”
- Photography or Social Media Focus: “Highlight destinations or routes with the best photo opportunities, unique architecture, or local life.”
Example Prompt
“I’m planning a ten-day trip in Germany starting in Berlin in August of this year. I’m most interested in visiting Hamburg, Cologne, Rothenburg, and Munich, returning to Berlin. I am open to others along the train route. I love discovering lively neighborhoods, street art, authentic local food, and walkable city centers. Please help me avoid overly touristy attractions and lengthy connections. I enjoy scenic train rides with great views for photography and would appreciate tips on comfortable trains, as well as easy food options, for travel between long-distance cities, particularly those that offer sleeper trains. My main goal is to experience culture, street art, history, and day-to-day life in each city at a relaxed pace.”
About Me Travel Prompt
“I love exploring old historic sections of a city, art and historical museums, maps, bookstores, and local food markets. I love learning about new things, especially the connection between a city and international trade, particularly a Silk Road connection. I prefer to walk as much as possible and use public transit for longer distances. My favorite food experiences involve local cuisine, specifically bread, wild game, dumplings, and local wine. I enjoy mild, sunny weather and have no mobility issues. My main travel goal is to get lost in authentic culture and take great photos for my blog, especially of unique architecture and street life.”
My avoids prompt
“Please avoid recommending activities or settings that involve large crowds, overly touristy attractions, noisy environments, or places that require long or complicated transit transfers. I’d also like to skip activities centered on nightlife, extreme sports, shopping malls, or rigid group tours. I prefer not to visit destinations with cruise ports and overly aggressive salespeople. I’d like to avoid restaurants catering to tourists or those with poor hygiene. I do not enjoy environments with intense sensory stimuli (such as bright lights or loud music). Please only suggest experiences that align with these preferences.”
Prompt for Upcoming Naples trip
- “Create a two-day itinerary for Naples, Italy, focusing on [interest, local food (Pizza and seafood), history, art, and old neighborhoods]. Assume I’m traveling as a couple.”
- “Suggest a walking tour route for Naples, Italy, including both iconic landmarks and authentic local spots.”
Next Steps
The prompts that follow aren’t meant to be copied word for word forever. They are a starting point.
As you travel more, and as AI learns more about what you enjoy, you should continue refining them. Add the experiences that delighted you. Remove the recommendations that fell flat. Teach AI which neighborhoods you loved, what restaurants exceeded expectations, how much walking you’re comfortable with, whether you prefer trains over buses, museums over shopping, hidden streets over famous landmarks.
Over time, your prompts become less of a checklist and more of a travel profile.
That’s the real lesson. The future isn’t about finding the perfect prompt. It’s about building better context.
The more AI understands your interests, preferences, constraints, and travel style, the less time you’ll spend filtering generic recommendations and the more likely you’ll discover experiences that feel as though they were chosen specifically for you.
In many ways, that’s true well beyond travel.
Whether you’re planning a vacation, researching a purchase, writing an article, or solving a business problem, AI produces its best work when it understands you. The more you teach it about how you think, what you value, and what success looks like, the more useful it becomes.
Don’t expect AI to read your mind.
Teach it how to think with you.
