Posted October 5, 2023

How to Use ChatGPT to Plan Your Winter Travel

Travel Tips

The AI hype is everywhere. Some say that AI will transform the economy, some say it will destroy humanity, and some say that AI will save the world. Our take? Who knows! But we like to focus on the practical. And the one thing we do know — with certainty — is that ChatGPT can be an incredibly useful tool right now, today, in planning your trips and vacations.

It’s time to hire that travel assistant you’ve always wanted. (Photo Credit: Caroline Selfors)

Think of ChatGPT as your whip-smart travel assistant who’s eager to please, is a hard worker, and will patiently answer your every question. But there is one catch: The better your prompts, the better the results, and if you’re not careful you can get misled.

Here are 10 ways to help ChatGPT plan your travel:

1. Request highly specialized itineraries

Think about your own hobbies and interests, then get ChatGPT to tailor an agenda around it.

For example: “Please give me a three-day itinerary for Paris that’s anchored around literary points of interest; include both the obvious stuff like Les Misérables, and also a few overlooked gems that only lit-nerds like me would appreciate.” 

Imagine all that time you’ll save, thanks to ChatGPT. (Photo Credit: Clarisse Meyer)

2. Gain cultural insight

Use ChatGPT to dig deeper into the local culture and ask about local legends, folklore, traditions, and customs of your destination.  

3. Ask open-ended questions

These can yield more thoughtful and expansive responses. For example: “What are some unique and lesser-known attractions in Honduras that are suitable for history lovers?” 

4. Request Pros and Cons

Especially if you’re comparing different travel options, ask for the pros and cons of each. For example: “Can you list the pros and cons of a ski trip in Aspen versus a sunny getaway in Ft. Lauderdale?” 

Simply pick the place you want to go. (Photo Credit: @element5)

5. Give feedback

Don’t be afraid to push and challenge ChatGPT. (They can take it. They love it!) You can tell it to get more creative, take more chances, be less obvious, or even to get a little funky.

For example: “Thanks for those suggestions. Now I’d like you to give me 10 more ideas, but make these more surprising, off-the-beaten path, and even a little weird. Impress me.” This gentle nudging helps them rise to the occasion.  

6. Ask ChatGPT to ask you questions

The more specific and personal information you can give ChatGPT about your travel preferences, the better the results. So, in your initial prompt, ask ChatGPT something like “Ask me any questions that will help you give me better answers.” 

And don’t forget to pack your bags. (Photo Credit: @oliur)

7. Give it a hyper-specific scenario

This is where the power of ChatGPT truly shines. It can fetch answers that would take forever through a traditional web search.

For example: “I only have 48 hours in Barcelona and I’m staying in the Kimpton Vividora Hotel, and I want to eat a LOT of good food; can you give me a culinary itinerary, factoring in that I want to walk to as many neighborhoods as possible? Oh, and don’t forget the desserts.” 

8. Ask incrementally

Break your queries into smaller, manageable parts.

So, you could start with general destination research, then a query for flights (using a plug-in such as Expedia or Kayak), then a query to recommend restaurants (requesting that it factor in Yelp reviews), and so on. 

Cheers to enjoying the best part of vacation. (Photo Credit: @dobarcelony)

Take me to Barcelona, ChatGPT. (Photo Credit: Nat Fernandez)

9. Ask for a reading list

Ask for a solid list of books, articles, and websites to help you better understand your destination. Don’t forget to ask for links to sources, which will help you sniff out hallucinations.

Which brings us to the final point… 

10. Double-check everything and beware of hallucinations

ChatGPT is excellent for help with brainstorming, weighing pros and cons, suggesting itineraries, and conducting both macro and micro research… But it can also – out of a desire to please you with a great answer – just flat-out make stuff up.

So, before you actually buy tickets or make hard plans, double-check its recommendations and take everything with a grain of artificial salt. 

Want to learn more about ChatGPT? Jeff Wilser has been experimenting with it constantly and is the host of a new podcast, AI-Curious.


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