How to Use AI to Plan a Trip: The Complete Step-by-Step Guide
Planning a trip used to mean hours of clicking through travel blogs, cross-referencing hotel reviews, and building spreadsheets by hand. In 2026, AI tools like ChatGPT, Claude, and Gemini can do most of that work in minutes — if you know how to ask.
This guide walks you through how to use AI to plan a trip from the first spark of an idea to the moment you zip your suitcase shut. Every step includes example prompts you can copy and paste directly into your favorite AI chatbot.
Why Use AI for Trip Planning?
Before we get into the steps, here's what AI actually does well (and where it falls short) when it comes to travel:
What AI is great at:
- Generating personalized itineraries based on your preferences, budget, and travel style
- Summarizing reviews and recommendations across dozens of sources
- Creating day-by-day schedules with realistic timing
- Suggesting alternatives you wouldn't have found on your own
- Building packing lists tailored to your destination and activities
- Translating phrases and explaining local customs
Where AI has limitations:
- Prices change constantly. AI can suggest where to look, but always verify flight and hotel prices on booking sites directly.
- Information can be outdated. AI models have training cutoffs. Double-check that restaurants, attractions, and transport routes are still operating.
- It doesn't know your taste perfectly. The more context you give, the better the results. Vague prompts produce generic itineraries.
The key to getting great results is specificity. Let's walk through each step.
Step 1: Destination Research
The best trip starts with the right destination. If you already know where you're going, skip to Step 2. If you're still deciding, AI can help you narrow it down.
Choose a Destination Based on Your Preferences
Instead of Googling "best vacation spots" and reading ten listicles, give AI your actual constraints and preferences:
Prompt: "I have 10 days off in late September. I want a destination that's warm (above 25C), affordable (under $100/day for food and accommodation), safe for solo travelers, and has a mix of beaches and cultural sites. I'm flying from New York. Suggest 5 destinations with a brief explanation of why each fits my criteria."
This single prompt replaces hours of research. The AI will factor in weather patterns, cost of living, flight availability, and safety data to give you tailored options.
Dive Deeper Into a Destination
Once you have a shortlist, ask follow-up questions:
Prompt: "Tell me more about visiting Portugal in late September. What's the weather like? Which regions are best for beaches vs. culture? How expensive is it compared to Spain and Greece? Any major festivals or events happening in September?"
Prompt: "What are the pros and cons of visiting Bali vs. Thailand in September? I care most about: low crowds, good food, easy to get around without a car, and opportunities for snorkeling."
Research Visa and Entry Requirements
Prompt: "I'm a US passport holder planning to visit Japan for 14 days. What are the current entry requirements? Do I need a visa? Are there any COVID-related restrictions still in place? What about travel insurance requirements?"
Pro tip: Always verify visa information on official government websites. AI gives you a solid starting point, but immigration rules change frequently.
Step 2: Build Your Itinerary
This is where AI truly shines. Instead of piecing together an itinerary from five different blog posts, you can generate a complete day-by-day plan in one prompt.
Generate a Full Itinerary
Prompt: "Create a 7-day itinerary for Lisbon and the Algarve region of Portugal in late September. I'm a solo traveler who enjoys:
- Walking tours and historical sites
- Local food markets and restaurants (mid-range budget)
- Beach time in the afternoons
- Photography opportunities
- Avoiding tourist traps
Include travel time between locations. Suggest which days to spend in Lisbon vs. the Algarve. For each day, include morning, afternoon, and evening activities with specific place names."
Customize by Travel Style
The more context you provide, the better your itinerary:
Prompt: "Adjust the itinerary for two changes: (1) I have a bad knee so I can't do long hikes or steep climbs — suggest alternatives. (2) I'd like to add a day trip to Sintra. Which day should I swap, and what's the best way to get there from Lisbon?"
Add a Budget Breakdown
Prompt: "For the Lisbon and Algarve itinerary you created, estimate daily costs in USD for: accommodation (mid-range hotel or quality Airbnb), meals (mix of restaurants and markets), local transport, and activity entrance fees. Give me a total estimated budget for the 7-day trip."
Create a Detailed Daily Schedule
Prompt: "Take Day 3 of my Lisbon itinerary and break it into a detailed schedule with specific times. Include restaurant recommendations for lunch and dinner near the areas I'll be visiting. Add any tips for that neighborhood (best time to visit, things to avoid, etc.)."
Step 3: Find the Best Flights
AI won't book your flights, but it can help you develop a smart search strategy.
Get Flight Search Advice
Prompt: "I need to fly from New York to Lisbon in late September for 7 days. What are the best strategies to find cheap flights on this route? Which airlines fly direct? What days of the week are cheapest to fly? Should I check any specific airports (like Newark vs. JFK)? What's a reasonable price range to expect?"
Compare Airports and Routes
Prompt: "Compare the options for flying from the NYC area to Lisbon: JFK, Newark, and LaGuardia. Which airlines fly direct from each? Are connecting flights through Madrid or London typically cheaper? What about flying into Porto instead and taking the train to Lisbon — is that worth considering?"
Timing Your Booking
Prompt: "When is the best time to book flights from the US to Portugal for a late September trip? How far in advance should I book? Are there specific days of the week when airlines release cheaper fares? What price tracking tools should I use?"
Important: Always book flights through official airline websites or established booking platforms like Google Flights, Skyscanner, or Kayak. AI helps you research, but it cannot access real-time prices.
Step 4: Find Hotels and Accommodation
AI can help you figure out where to stay, what to look for, and what to expect — without scrolling through hundreds of listings.
Get Neighborhood Recommendations
Prompt: "I'm staying in Lisbon for 4 nights. Recommend the best neighborhoods to stay in for a solo traveler who wants to walk to restaurants, attractions, and nightlife. For each neighborhood, tell me: the vibe, price range for a mid-range hotel, pros and cons, and how well-connected it is to public transport."
Narrow Down Accommodation Type
Prompt: "For a 7-day trip to Portugal (4 nights Lisbon, 3 nights Algarve), should I book hotels, Airbnbs, or hostels? I'm solo, my nightly budget is $80-120, and I value: reliable Wi-Fi, central location, and meeting other travelers. Give me the pros and cons of each option for both locations."
What to Look For in Reviews
Prompt: "What should I look for when reading hotel reviews for Lisbon? What are common complaints about hotels in the Alfama and Baixa neighborhoods? Any red flags I should watch for on booking sites?"
Step 5: Local Recommendations
Generic tourist guides give you the same 10 recommendations everyone else sees. AI can go deeper when you give it specific preferences.
Find Restaurants Like a Local
Prompt: "Recommend 10 restaurants in Lisbon that locals actually eat at (not tourist traps). I want: 3 for traditional Portuguese food, 3 for seafood, 2 for casual lunch spots, and 2 for special dinner experiences. For each, tell me the price range, what to order, and which neighborhood it's in. My budget is $15-40 per meal."
Discover Hidden Gems
Prompt: "What are 5 things to do in Lisbon that most tourists miss? I'm not interested in the typical 'top 10 attractions' list. I want local neighborhoods to wander, lesser-known viewpoints, unique shops, and experiences that give me a real feel for the city."
Plan Day Trips
Prompt: "What are the best day trips from Lisbon that I can do by public transport (no rental car)? For each, tell me: how to get there, how long it takes, what to do there, estimated cost, and whether it's worth the time."
Navigate Transportation
Prompt: "Explain the public transport system in Lisbon. What card or pass should I buy? How do I get from the airport to the city center? Is Uber/Bolt available and affordable? What about getting from Lisbon to the Algarve — train, bus, or domestic flight?"
Step 6: Prepare for Your Trip
The practical details can make or break a trip. AI handles the boring-but-essential planning surprisingly well.
Create a Custom Packing List
Prompt: "Create a packing list for a 7-day trip to Portugal in late September. I'm a male solo traveler. Activities include: city walking tours, beach days, a few nice dinners, and a day hike. The weather will be 20-28C (68-82F). I want to pack carry-on only (40L backpack). Organize the list by category and highlight the items people most commonly forget."
Learn Essential Phrases
Prompt: "Teach me the 20 most useful Portuguese phrases for a tourist in Lisbon. Include: greetings, ordering food, asking for directions, shopping, and emergencies. Show the Portuguese phrase, a phonetic pronunciation guide, and the English translation."
Understand Local Customs and Etiquette
Prompt: "What should I know about Portuguese culture and etiquette as a visitor? Cover: tipping customs, dining etiquette, dress codes for churches or restaurants, common scams to watch for, and any behaviors that might be considered rude."
Plan Your Budget
Prompt: "Create a detailed daily budget for a solo traveler in Portugal in September 2026. Break it down into: accommodation, food (breakfast, lunch, dinner, snacks), transport, activities/entrance fees, and miscellaneous. Give me three budget levels: backpacker, mid-range, and comfortable. Use USD."
Step 7: Handle Trip Logistics
These are the details that experienced travelers always sort out in advance.
Build a Travel Document Checklist
Prompt: "Create a complete checklist of documents and preparations I need before traveling from the US to Portugal. Include: passport requirements, travel insurance, health preparations, phone/data plan options, bank notifications, emergency contacts, and digital copies of important documents. Tell me which items to handle 1 month before, 1 week before, and the day before departure."
Plan for Connectivity
Prompt: "What are my options for phone and internet access in Portugal? Compare: international roaming from my US carrier, buying a local SIM card, using an eSIM service, and relying on Wi-Fi. Which option gives the best value? Any specific eSIM providers you'd recommend?"
Create a Safety Plan
Prompt: "What safety tips should I know as a solo traveler in Portugal? Cover: which areas to avoid at night, common tourist scams in Lisbon, emergency numbers, nearest US embassy location, travel insurance recommendations, and general safety practices for solo travelers in Southern Europe."
Step 8: During Your Trip
AI remains useful after you land. Keep your AI chatbot handy on your phone for real-time help.
Get Real-Time Recommendations
Prompt: "I'm currently in the Alfama neighborhood in Lisbon. It's 1 PM and I'm hungry. Recommend 3 lunch spots within walking distance that serve traditional Portuguese food for under $20. I want something casual where I can sit down and rest my feet."
Handle Unexpected Changes
Prompt: "It's raining in Lisbon today and my plan was outdoor sightseeing. Suggest 5 indoor activities I can do instead. I'm near the Baixa-Chiado area. Include museums, markets, and any unique indoor experiences."
Translate and Communicate
Prompt: "How do I say these things in Portuguese? (1) 'I have a food allergy to shellfish' (2) 'Can I get the check please?' (3) 'Where is the nearest pharmacy?' (4) 'Does this bus go to Belem?'"
Make Dining Decisions
Prompt: "I'm looking at a menu in Portuguese and I don't understand some items. Here's what I see: bacalhau a bras, arroz de marisco, caldo verde, francesinha, pasteis de nata. Explain each dish, what it tastes like, and which ones are must-tries."
Best AI Tools for Trip Planning
Different AI tools have different strengths for travel planning:
| Tool | Best For | Free Access | Key Strength |
|---|---|---|---|
| ChatGPT | General itineraries, restaurant recs | Yes (GPT-4o) | Web search for current info |
| Claude | Detailed planning, long itineraries | Yes (Sonnet) | 200K context for complex trips |
| Gemini | Google Maps integration, local info | Yes | Deep Google ecosystem access |
| Perplexity | Fact-checking, sourced answers | Yes | Citations with every answer |
| Copilot | Quick searches, Bing integration | Yes | Real-time web results |
For the best results, use more than one tool. Generate your itinerary with Claude or ChatGPT (they handle long, detailed plans well), then verify specific details like restaurant hours and prices with Perplexity or a Google search.
Tips for Getting Better AI Travel Advice
After planning dozens of trips with AI, here's what separates a mediocre result from a great one:
1. Be specific about who you are "Plan a trip to Tokyo" gives you a generic guide. "Plan a trip to Tokyo for a couple in their 30s who love street food, vintage shopping, and avoiding crowds" gives you something you'll actually use.
2. Include your constraints Budget, physical limitations, dietary restrictions, travel dates, group size — every constraint helps the AI narrow down its recommendations.
3. Ask for alternatives
"Give me your top recommendation AND two alternatives for each" — this prevents you from missing better options.
4. Iterate and refine Your first prompt is a starting point. Ask follow-up questions. Say "adjust this because..." or "I don't like that suggestion, replace it with something more..." The conversation is where the real value is.
5. Always verify critical details AI is excellent for planning and discovery, but verify prices, opening hours, visa requirements, and safety information through official sources. Think of AI as your smart travel-planning assistant, not an infallible guidebook.
6. Save your conversation Most AI tools let you keep your chat history. Your planning conversation becomes a reference document you can search during your trip.
Sample Complete Trip Plan
Here's what a complete AI-planned trip workflow looks like in practice:
Week 1 (4+ weeks before):
- Ask AI to suggest destinations matching your criteria
- Research 2-3 top options with follow-up prompts
- Generate a rough itinerary for your top choice
- Get flight search strategy and start monitoring prices
Week 2 (3 weeks before): 5. Book flights and accommodation 6. Ask AI to refine your itinerary with specific hotels/areas 7. Generate restaurant and activity recommendations 8. Create a budget breakdown
Week 3 (2 weeks before): 9. Generate your packing list 10. Get a document/preparation checklist 11. Learn essential phrases 12. Research local customs and transport
Week 4 (1 week before): 13. Ask AI for a final daily schedule with times 14. Get weather-specific clothing advice 15. Generate a safety and emergency info sheet 16. Download offline maps and save key addresses
Frequently Asked Questions
Can AI really plan a whole trip?
Yes, AI can handle most of the research and planning work. It generates itineraries, finds recommendations, creates packing lists, and helps with logistics. However, you still need to book flights, hotels, and activities yourself, and you should verify time-sensitive details like prices and availability on booking platforms.
Which AI tool is best for trip planning?
ChatGPT and Claude are the best general-purpose tools for trip planning. ChatGPT has web search built in for current information. Claude handles very long, detailed itineraries well thanks to its large context window. For fact-checking specific details, Perplexity provides sourced answers. Using a combination gives the best results.
Is AI travel planning free?
Yes. ChatGPT, Claude, Gemini, and Perplexity all offer free tiers that are more than sufficient for trip planning. You don't need a paid subscription to generate itineraries, get recommendations, or create packing lists.
How accurate are AI travel recommendations?
AI recommendations are generally reliable for well-known destinations, but accuracy varies. Restaurant recommendations, cultural information, and general travel advice tend to be solid. Prices, opening hours, and very specific details (like bus schedules) may be outdated. Always verify critical information through official sources before your trip.
Can AI find cheap flights and hotels?
AI can advise you on when and where to search for deals, which airlines fly specific routes, and what price range to expect. It cannot access real-time booking systems, so you'll need to search platforms like Google Flights, Skyscanner, or Booking.com yourself. The AI strategy + human execution approach usually finds better deals than browsing randomly.
Should I trust AI for visa and safety information?
Use AI as a starting point, not the final word. AI can outline general visa requirements and safety considerations, but immigration rules and travel advisories change frequently. Always verify visa requirements on official embassy or government websites, and check current travel advisories from your country's state department.
How do I get AI to give me non-touristy recommendations?
Be explicit in your prompts. Say "recommend places locals go, not tourist attractions" or "I want to avoid anywhere that appears in the top 10 TripAdvisor results." You can also ask: "What would you recommend to a friend who lives in [city] and wants to show a visitor the real version of the city?"
Can I use AI for travel planning during my trip?
Absolutely. Keep your AI app on your phone for real-time restaurant recommendations, translation help, navigating unexpected changes (like rain), understanding menus, and finding nearby activities. The AI chatbot essentially becomes a personal travel concierge you can ask anything at any moment.
Start Planning Your Next Trip
AI doesn't replace the joy of travel — it removes the tedious parts of planning so you can focus on the experience itself. What used to take days of research now takes an evening of conversation with an AI assistant.
Open ChatGPT, Claude, or whichever AI tool you prefer, and start with the simplest prompt: "Help me plan a trip." Then let the conversation guide you from there.
Want to get even better at working with AI? Our free Prompt Engineering course teaches you how to write prompts that get better results for any task — including travel planning. And if you're curious about how AI tools work under the hood, check out AI Essentials for a beginner-friendly introduction.