How to Plan a Trip with AI

Before asking the AI for anything, write down the basics in a document or note:

1. Destination: a country, a city or a region? If you’re not sure, ask AI to suggest options based on your budget and the time of year.
2. Dates and duration: how many days do you have? Are there fixed dates (a return flight already booked)?
3. Estimated total budget, including flights, hotel, food and activities.
4. Group profile: solo, couple, family (with kids? with older adults?), friends.
5. Interests: culture, food, adventure, beach, mountains, history, nightlife, shopping.

With that information in hand, the prompt you give the AI will produce much more useful results.

Example prompt to start:

I want to plan a 7-day trip to Portugal (Lisbon and Porto) for 2 people in October. Total budget of $3,000 USD including flights from Miami. We're interested in food, history and viewpoints. No children. Suggest a general itinerary and the best times to visit each city.

If you still don’t know where to go, start with: “Suggest 3 destinations for a 7-day trip in October with $2,500 USD per person from [your city], focused on nature and food.”

Perplexity AI is ideal for this step because it searches the web in real time and cites sources, so you can verify every detail before booking.

1. Go to perplexity.ai and sign in.
2. Paste the prompt from Step 1 and send it.
3. Read the result and refine it with follow-up questions:

Now create an hour-by-hour itinerary for all 7 days. Include estimated travel time between Lisbon and Porto, the best local (non-touristy) restaurants, the most important museums with approximate hours and prices, and a rainy-day alternative for each day.

4. If you want more detail on a specific day, ask:

Expand Day 3 in Porto. I want to explore the Ribeira area in the morning, try port wine in the afternoon and have a nice dinner without spending more than $40 per person.

What you get: an itinerary with real places, suggested times, transport options and practical notes. Save it in your document.

To get more out of Perplexity AI, check the tutorial How to Use Perplexity AI to Research the Web.

AI can’t book for you, but it helps you know what to search before opening the platforms.

For flights:

1. Ask Perplexity AI:

Which airlines fly from Miami to Lisbon in October? Which have shorter layovers? How far in advance should I buy to find a good price?

2. With that information, go to Google Flights (flights.google.com), turn on the calendar view to see the cheapest days and filter by number of stops.

For accommodation:

1. Ask the AI for a neighborhood recommendation:

Which neighborhood in Lisbon is best to stay in to get around easily on foot and be close to the main tourist spots? Recommend the type of accommodation (boutique hotel, apartment, hostel) with a budget of $120/night for 2 people.

2. Then search those options on Booking.com or Airbnb with exact dates.

Important: always compare the price the AI gives you with the current price on the platform. Prices change constantly and the AI may have data from previous weeks.

With the itinerary, flights and hotel defined, Claude helps you organize everything into a budget table.

1. Open claude.ai and sign in.
2. Paste all your data and ask for the breakdown:

I'm planning a 7-day trip to Portugal for 2 people in October. Flights: $900 (found on Google Flights). Hotel in Lisbon 4 nights: $480. Hotel in Porto 3 nights: $300. I need to estimate the cost of meals (local restaurants, no luxury), internal transport (Lisbon-Porto train and metro), museum entrance fees and miscellaneous. Build a budget table with the total and tell me if I'm within $3,000 USD.

3. If the number exceeds your budget, ask for ways to cut:

The estimate is $400 over my budget. What can I adjust to lower the cost without sacrificing the most important parts of the trip?

The result: a clear table with each category, estimated amounts and a total. Save it alongside the itinerary.

For more budget management strategies with AI, check the tutorial How to Use AI to Manage Your Personal Finances.

Before traveling, ask the AI to generate a checklist of documents and preparations for your destination:

I'm traveling to Portugal in October as a citizen of [your country]. What documents do I need (passport, visa, travel insurance)? Are there any entry requirements I should know about? What mobile apps do you recommend having installed before I arrive?

Also ask it to anticipate common problems:

What are the most common mistakes tourists make in Lisbon and Porto and how can I avoid them? Include tips about transport, safety, tipping and local customs.

Documents you typically need:

• Valid passport (at least 6 months of validity)
• Travel insurance (highly recommended; check medical coverage)
• Flight and hotel reservations printed or saved offline
• Debit/credit card with low international transaction fees
• Apps: Google Maps offline, Google Translate, your bank’s app

Always verify entry requirements on the official consulate or embassy website for your destination, as they can change.

If you want to do everything in one conversation, use this master prompt in Perplexity AI or Claude. Copy it, fill in the blanks and send it:

Act as an expert travel planner. I want to plan a trip with the following details:
- Origin: [your city]
- Destination: [city or country]
- Dates: [departure date] to [return date] ([N] days total)
- Travelers: [number of people and profile: couple, family with kids, friends, etc.]
- Total budget: $[amount] USD (includes flight, hotel, food and activities)
- Interests: [list your interests: food, culture, nature, etc.]
- Restrictions: [allergies, limited mobility, tight food budget, etc.]

Please:
1. Suggest a day-by-day itinerary with the main activities, recommended times and transit times between places.
2. Recommend the best neighborhoods to stay in and the right type of accommodation.
3. Include the most recommended local restaurants (non-touristy).
4. Build an estimated budget table by category (flight, hotel, food, transport, activities, misc).
5. List the documents and preparations I need based on my home country.
6. Mention the most common mistakes tourists make and how to avoid them.

With this prompt you get everything in one response. Then you can dig into each section with follow-up questions.

Problem	Fix
The AI gives me prices very different from real ones	Prices change constantly; use them only as a reference and always verify on Google Flights or Booking.com
The itinerary is too generic	Be more specific in your prompt: mention your daily budget, the types of activities you enjoy and how many hours a day you want to walk
The AI says it doesn’t have up-to-date information	Use Perplexity AI instead of Claude for price and availability searches, since it accesses the web in real time
I don’t know if I need a visa	Ask the AI and then verify on the official consulate website of the destination country; AI can make mistakes on immigration requirements