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How to Use AI to Plan a Trip

There is no doubt that artificial intelligence (AI) has made astounding (and sometimes worrying) progress over the past two years. ChatGPT in particular has captured public fascination. People have been using the ChatGPT AI for all sorts of things, from proofreading to fact-checking (with varying degrees of success). Since ChatGPT is able to source data from all over the internet, is it possible to use it for travel planning as well? Yes it is, but at least for now, you need to be specific about how you use it. So here are some tips about how to use AI to plan a trip.

Disclaimer: This article was 100% written by a human being! We promise that this is written by humans for humans.

What is ChatGPT? – How to Use AI to Plan a Trip

In a nutshell, ChatGPT(Chat Generative Pre-Trained Transformer) is an AI chatbot, a type of software designed to replicate human conversation. It allows users to guide the bot’s responses by specifying details, styles, and so on. ChatGPT differs from other bots because it can keep track of the context of its conversations by remembering what users have previously said.

However, as of now, ChatGPT only has knowledge of date sourced until 2021. It has no knowledge of current events afterwards. This may or may not change in the future, but this is the current state of the free version. It can also lag or freeze depending on how many users are accessing it at the same time.

Next, it is important to remember that for all its capabilities, ChatGPT does not have a brain of its own. When using it, you have to guide it through its answers by prompting it to say what you need or want to see.

Tip: ChatGPT is a powerful AI tool, but always take its answers with a grain of salt.

There are a number of ways you can access ChatGPT. The easiest method is to go to and sign in through Apple ID or a Google or Microsoft account. Once you sign in, you have access to the chatbot. There is currently a free version available for anyone to use, but users will have to pay for anything more advanced. For our purposes, the free version is more than enough.

Photo by Andrew Neel

How to Use AI to Plan a Trip

Although some travelers have taken to planning entire trips and itineraries with ChatGPT, at this time, we recommend simply using the AI as a planning tool instead. ChatGPT itself also frequently tells users not to take its words as law. We need to remember that the AI is merely a tool that outputs data from other sources; it is not a free-thinking person that can travel in the physical world. As such, it can only feed you information related from other sources, which makes ChatGPT just another research tool. It cannot relate anything firsthand nor can it understand human experience (it can only regurgitate experience from other humans). It is however, a research tool that you can streamline and tailor to your needs.

Using AI as a Tool – How to Use AI to Plan a Trip

We highly recommend against using ChatGPT as a travel guide or search engine. As mentioned, its knowledge currently ends at 2021. In the AI’s own words, it cannot access real-time information or personal experience. It can only draw from publicly available data. For example, I asked it what tourists should be careful about while visiting Sicily. After it provided a generic list of concerns, I asked it how it came up with its response.

ChatGPT’s Answer

[As an AI language model, my responses are generated based on a mixture of licensed data, data created by human trainers, and publicly available data. I don’t have direct access to real-time information or personal experiences.

For the response about what tourists should be careful about when visiting Sicily, I drew upon my training on a diverse range of information sources such as travel guides, tourism websites, safety advisories, and general knowledge about common precautions for travelers. I strive to provide useful and relevant information based on the input provided by users.

It’s important to note that while I aim to offer accurate and up-to-date information, situations can change, and it’s always a good idea to consult official sources, travel advisories, or trusted websites for the latest information and guidance regarding travel safety and precautions in Sicily or any other destination.]

Our Takeaway

The answer tells us two important things. One: ChatGPT generates answers regarding travel based on the most common and widely cited questions and concerns. Two: ChatGPT has access to travel guides, safety advisories, and tourism websites. This means we can use ChatGPT as a quick way to see what the most common or popular concerns and questions are about our travel destination. We can also assume that the answers are from trustworthy resources (though we still encourage manually verifying the information as well). Now, we discuss how to use AI to plan a trip using the Sicily example.

Asking the Right Questions – How to Use AI to Plan a Trip

ChatGPT’s answers are only as specific as your questions, so the vaguer the prompt, the vaguer the answer. Using a hypothetical Sicily trip as an example, I told the AI to help me plan a trip to Sicily (with no other specifications). To its credit, ChatGPT provided a rather lengthy answer, but as you can see, the answer has barely any substance:

ChatGPT’s Answer

[1. Determine the duration of your trip: Decide how long you want to spend in Sicily. This will help you allocate your time effectively and plan your itinerary.

2. Choose the best time to visit: Sicily has a Mediterranean climate, with hot summers and mild winters. The shoulder seasons of spring (April to June) and fall (September to October) are generally considered the best times to visit, as the weather is pleasant, and the tourist crowds are smaller.

3. Decide on your points of interest: Sicily offers a wide range of attractions, so it’s important to identify the places you’d like to visit. Some popular destinations include Palermo, Taormina, Syracuse, Agrigento, Catania, and Mount Etna. Each city has its own unique charm and attractions, so research them to find the ones that align with your interests.

4. Plan your itinerary: Once you’ve decided on the places you want to visit, create a rough itinerary. Consider the travel distances between cities and allocate time accordingly. Remember to factor in some relaxation time and flexibility to explore the local culture and cuisine.

5. Transportation: Sicily has a well-connected transportation network. You can fly into Catania or Palermo, the two major airports on the island. To explore Sicily, you can rent a car, use public transportation like buses and trains, or hire a private driver for more convenience. Renting a car gives you greater flexibility, especially if you plan to explore rural areas.

6. Accommodation: Look for accommodations that suit your budget and preferences. Sicily offers a range of options, including luxury hotels, boutique B&Bs, agriturismi (farm stays), and vacation rentals. Consider staying in different locations to experience various parts of the island.

7. Explore local cuisine: Sicilian cuisine is renowned for its unique flavors influenced by Arab, Greek, and Italian cultures. Be sure to try iconic dishes like arancini (rice balls), cannoli (pastry shells filled with sweet ricotta), pasta alla Norma, and fresh seafood dishes. Don’t forget to pair your meals with Sicilian wines!

8. Cultural and historical sites: Sicily is rich in history and boasts several UNESCO World Heritage Sites. Visit attractions like the Valley of the Temples in Agrigento, the ancient city of Syracuse, the Norman Palace in Palermo, and the Greek Theatre in Taormina.

9. Relax on the beaches: Sicily is known for its beautiful beaches and crystal-clear waters. Spend some time unwinding on the sandy shores and swimming in the Mediterranean Sea. Some popular beach destinations include Cefalù, San Vito Lo Capo, Mondello, and the Aeolian Islands.

10. Pack appropriately: Check the weather forecast for your travel dates and pack accordingly. Bring comfortable footwear for walking, lightweight and breathable clothing, sunscreen, a hat, and a reusable water bottle for staying hydrated.]

Our Takeaway

The AI mentioned some popular attractions, sites, and foods in Sicily to look out for, but it offers no information about how to access them. It vaguely mentions the best time to visit, but doesn’t tell us when would be best to visit the individual attractions it suggested. The AI does not recommend hotels or specific methods of transportation (or price!). It mostly tells you what you already know and requires you to do the rest of the research yourself. You can, however, still use the AI to help you start that research by narrowing down your questions.

Also see Jenny in Wanderland article How to Travel to a Place You Have Never Been

Narrowing Down Your Questions – How to Use AI to Plan a Trip

Photo by Jennifer Barbaro

Simply telling ChatGPT to plan a Sicily trip for you will not generate any useful results. So we will make the question more specific. I asked it when would be best to visit Sicily. The result was still vague, but much more specific.

ChatGPT’s Answer

[To avoid crowds and enjoy a more peaceful experience, it’s generally recommended to visit Sicily during the shoulder seasons of spring (April to June) and fall (September to October). Here’s a breakdown of the advantages and considerations for each season:

1. Spring (April to June):

– Weather: The temperatures are mild, ranging from around 15°C to 25°C (59°F to 77°F), making it pleasant for outdoor activities.

– Landscape: The countryside is lush and green, and flowers are in bloom, creating a picturesque backdrop.

– Crowds: The tourist crowds are generally smaller compared to the peak summer season, but it can get busier during Easter holidays and local festivals.

– Accessibility: Many attractions, accommodations, and services are open but not yet operating at full capacity.

– Events: Various local festivals and events take place during spring, providing an opportunity to experience Sicilian traditions.

2. Fall (September to October):

– Weather: The temperatures remain pleasant, ranging from around 18°C to 27°C (64°F to 81°F), allowing for comfortable exploration.

– Landscape: The vineyards and olive groves are in harvest season, creating a scenic ambiance. The sea is still warm for swimming.

– Crowds: The crowds tend to be smaller compared to the peak summer season, as many tourists have returned home. However, keep in mind that popular attractions may still have some visitors.

– Accessibility: Most services and attractions are open, and the island is less crowded, allowing for a more relaxed experience.

– Events: September is a great time for wine enthusiasts as it’s the start of the grape harvest, and various wine festivals are organized across the island.]

Our Takeaway

Looking at this answer, we have a better idea of what Sicily’s weather is like and what to expect during the spring and fall. The answers do not tell us which specific attractions are less crowded or which events are generally available. You can ask it to specify, but we believe it would be easier to fill in the rest of that information yourself but searching for what attractions and events are available during your desired travel period.

Analyzing the Answer – How to Use AI to Plan a Trip

On the flip side, ChatGPT providing this answer also means every other travel guide out there is likely saying the same thing. If all travelers are told to visit Sicily in the fall and spring to avoid crowds, there would still be an influx of travelers. In this case, it is important to read into what information the AI did not manage to grab. It never mentioned the winter season. I then researched (with other travel sources) the tourist scene in Sicily during winter.

As it turns out, Sicily has little crowds during the winter season and it is easier for jetsetters to find discounted rates on travel and accommodations (except in areas close to Christmas markets or other holiday festivities). Of course, the downside to winter travel in Sicily involves colder weather, potentially less activity in terms of beaches, and the possibility of closed transportation services. Going by this information, travel sources (and therefore ChatGPT) do not recommend winter as the best time to visit Sicily with good reason. However, that does not make traveling to Sicily in winter necessarily worse than other seasons. If anything, looking more into winter travel provides you with another (even possibly better) option for your trip!

Planning the Trip – How to Use AI to Plan a Trip

After settling on a hypothetical timeframe for the Sicily trip, I decided to get even more specific with my questions. I still need to know how to travel to Sicily, where to actually visit, which hotel to stay in, which transportation to use when in Sicily, and what to watch out for. I don’t expect ChatGPT to have clear-cut answers for everything, but I want to use it as a springboard for my own research and as a checklist shortcut.

Using New York as a potential starting point for the trip, I asked ChatGPT to recommend airlines that provide good deals for trips from New York to Sicily. Obviously, the AI cannot provide actual prices due to its limitations, but the answers gave me a good idea about which airlines could offer the best promotions.

ChatGPT’s Answer

[1. Delta Air Lines: Delta Air Lines is a major U.S. carrier that operates flights from New York to Sicily. They offer direct flights from John F. Kennedy International Airport (JFK) to Palermo Airport (PMO) and Catania Airport (CTA). Delta frequently provides competitive prices and promotions, so it’s worth checking their website or signing up for fare alerts.

2. Alitalia: Alitalia, the national airline of Italy, operates flights from New York to Sicily with connections in Rome or Milan. They offer several daily flights from John F. Kennedy International Airport (JFK) to both Palermo Airport (PMO) and Catania Airport (CTA). Alitalia often has competitive fares and provides a range of fare options to suit different budgets.

3. Air France: Air France, a major international airline, offers flights from New York to Sicily with connections in Paris. They operate flights from John F. Kennedy International Airport (JFK) to both Palermo Airport (PMO) and Catania Airport (CTA). Air France occasionally offers attractive deals and promotions, especially if you book well in advance.

4. Lufthansa: Lufthansa, a renowned German airline, provides flights from New York to Sicily with connections in Frankfurt or Munich. They operate flights from John F. Kennedy International Airport (JFK) to both Palermo Airport (PMO) and Catania Airport (CTA). Lufthansa often offers competitive fares and has a reputation for quality service.

5. British Airways: British Airways, the flag carrier of the United Kingdom, offers flights from New York to Sicily with connections in London. They operate flights from John F. Kennedy International Airport (JFK) to both Palermo Airport (PMO) and Catania Airport (CTA). British Airways occasionally provides attractive fares and promotions, particularly during off-peak travel periods.]

Back to Planning – How to Use AI to Plan a Trip

When I asked ChatGPT to recommend flight search engines, it provided a number of websites that allow users to find and compare flights. Trip Advisor and were among the websites. These websites allow real time comparisons and the ability to purchase your airfare right here and now.

Then I asked the AI to suggest a hotel in Catania. Since there are so many hotels in Sicily, it is important to be specific about where you want the hotel to be and what other conditions you have. I said the following: “Suggest a hotel in Catania for me to stay in during my 5 day trip. I am budgeting for $200 per night, but would like somewhere close to the attractions. It also needs to be safe and not part of a business chain (Ex. No Hiltons or Marriotts).”

ChatGPT suggested the Hotel Mercure Catania Excelsior, based on my preferences and the hotel’s popularity among other tourists. It provided the hotel’s address, an overview of amenities, and proximity to attractions and public transport. I was actually quite impressed with the answer. “This is so much easier than using search engines!” I thought. Then I Googled the hotel and learned it was temporarily closed. Although it has since reopened (if reviews from 2023 are anything to go by), the experience tells me that we need to be wary of ChatGPT’s suggestions. It never mentioned the temporary closing because it had no knowledge of it. We can use ChatGPT to suggest hotels, but it is up to us to double-check the information and look over reviews from other guests. After all, ChatGPT gets its information from the hotel’s words, not its guests, much less disgruntled guests.

Think Realistically – How to Plan a Trip with AI

When I asked ChatGPT what travelers need to be most careful about in Sicily, it gave me a comprehensive list of safety precautions (such as scams, pickpocketing, overheating, natural hazards, and delays in public transport). If you were to plan a trip to Sicily, the list would certainly work as a good reminder. As with attractions, the most popular cautionary tips always come from experienced sources. Of course, ChatGPT’s safety tips must go hand in hand with current events (remember: it has no access to real-time information after 2021!).

For the same reasons, we can ask ChatGPT what the safest and most efficient forms of public transport are in Sicily (specifically Catania and Palermo). From there, we can ask it to suggest routes (Ex. bus routes and metro routes) for our destinations. That said, we feel that ChatGPT listing popular forms of transports is enough. Anything else runs the risk of being incorrect due to the AI’s knowledge limitations. We can then research the routes ourselves by looking at experiences from other travelers and locals on THIS awesome site, where you can compare routes on trains, buses and flights and purchase tickets in real time.

As for itineraries, you can decide how you want to use ChatGPT to contribute. We could ask it to generate a one-day itinerary in Catania. It did so quickly, generating a day full of activities, including suggested attractions and cuisine. However, it did not name any specific hour or restaurant. If you want flexibility in your schedule and intend to use the AI’s itinerary as a checklist of things to research, this kind of response is all you need from it.

For a more specific itinerary draft, we need to ask a more specific question. I told it to the following: “Generate a one-day itinerary in Catania that starts in the afternoon. Suggest specific restaurants to try and shops to visit. Include the exact times of day and avoid tourist traps.”

ChatGPT’s Answer

[This itinerary is designed to avoid tourist traps and focus on experiencing authentic local spots in Catania. The specific times mentioned are approximate and can be adjusted based on your preferences.


1:30 PM – Arrival in Catania: Arrive in Catania and check-in to your accommodation.

2:00 PM – Lunch at Trattoria da Antonio: Start your afternoon with a delicious Sicilian lunch at Trattoria da Antonio (Via Santa Filomena, 21). This family-run trattoria offers authentic and hearty Sicilian dishes in a cozy and welcoming atmosphere.

3:30 PM – Explore Piazza Duomo: After lunch, head to Piazza Duomo, the heart of Catania. Take your time to explore the stunning Catania Cathedral (Duomo di Catania), an impressive Baroque masterpiece, and marvel at the Elephant Fountain (Fontana dell’Elefante), a symbol of the city.

4:30 PM – Wander through the Fish Market: Walk to the lively and vibrant Fish Market (La Pescheria) near Piazza Duomo. Experience the bustling atmosphere as local vendors sell an array of fresh seafood, fruits, and vegetables. Take in the lively ambiance and unique sights and sounds of this authentic market.

5:30 PM – Sicilian Granita Break at Caffè Sicilia: For a refreshing break, head to Caffè Sicilia (Via Etnea, 300), a famous historic café renowned for its traditional Sicilian sweets and granita. Try the classic almond or lemon granita, a delightful local specialty.

6:30 PM – Stroll down Via Etnea: Take a leisurely stroll down Via Etnea, Catania’s main shopping street. Explore various local shops and boutiques, including artisanal craft shops, fashion boutiques, and specialty stores.

7:30 PM – Dinner at Osteria Antica Marina: Conclude your afternoon with an authentic Sicilian dinner at Osteria Antica Marina (Via Antonino di Sangiuliano, 68). This restaurant offers a selection of traditional Sicilian dishes made with fresh, locally-sourced ingredients.

9:00 PM – Gelato at Gelateria Savia: End your day with a delicious gelato from Gelateria Savia (Via Etnea, 300), a renowned gelato shop with a variety of flavors to choose from. Enjoy your treat while taking in the city’s evening atmosphere.

This itinerary allows you to experience the best of Catania in a day, including authentic dining experiences and local shopping, while avoiding tourist traps and embracing the city’s true essence. Remember to make reservations in advance for dinner to secure a spot at Osteria Antica Marina and take note of any seasonal hours or closures for the shops and restaurants.]

Our Takeaway

This itinerary is much more detailed. Using this, there are far more attractions and eateries we can look into on our own. The AI also reminds us to be aware of Osteria Antica’s popularity, which means this is a common warning across the internet. However, the hour-by-hour setup is not realistic at all. ChatGPT did not take into account time needed for queues, transportation, or bathroom breaks. It might be possible to do everything it suggested in that order, but it would not be realistic.

This reminds us that ChatGPT is first and foremost a machine that can do what you want on the surface, but ultimately cannot account for human experience. That is why we say ChatGPT is best as a research tool when discussing how to use AI to plan a trip. For help with an itinerary, you can ASK JENNY and receive a personal human response from Jenny in Wanderland, and have other travelers weigh in too!

Tour this medieval village, learning the history while winding through ancient alleys and exploring the castle!

Generate a Packing List – How to Use AI to Plan a Trip

Although you can’t rely on AI to do your packing for you, you can use it to generate a packing checklist. When I asked it to suggest a packing list for five days in Sicily in September, it churned out a generic list of items most travelers would bring on any trip to Europe. It also suggested a few items you may not have thought to name such as antihistamines (which I never travel without) and daypacks (or beach bags), which you could use to carry essential items while exploring attractions in the daytime. Since ChatGPT suggested sun protection in the list, I asked the AI to recommend some sunblock brands for sensitive skin. It successfully did so, suggesting real brands I could look into.

Pretending I packed my suitcase, I then asked ChatGPT to remind me of anything I forgot to pack. My prompt: “I have packed my suitcase. My items: clothes, charger and adapter, identity verification, cash. What did I forget to pack?” The AI again answered with a generic list of essential items (such as travel documents and toiletries) I would never forget. Interestingly, it also suggested some items you may not have thought about on your own: travel size laundry detergent or stain pens (which I always carry), and travel locks to secure luggage.  Both of these items could come in handy and are things some travelers wouldn’t think to take along.

Future Travel

For trips in the future, we can use the same method to receive suggestions about items we would not think to pack off the top of our heads. We would need to draft our own packing list first. Then we can input it into ChatGPT and ask it if we forgot anything, prompting more interesting answers. The majority of results might be generic, but there might also be good tips among them.

Also see Jenny in Wanderland’s Free Travel Packing Visualization Exercise

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