yeti logo icon
Close Icon
contact us
Yeti postage stamp
We'll reply within 24 hours.
Thank you! Your message has been received!
A yeti hand giving a thumb's up
Oops! Something went wrong while submitting the form.

ChatGPT: The Ultimate Guide to Vacation Planning

Rudy Mutter
May 2, 2023
person using chat gpt to plan a vacation

We all love a good vacation. Good food, exciting adventures and most importantly... relaxing. But let's be real... planning a vacation, especially a multi-week international trip, is a huge time suck - and not relaxing in the least.

I generally pride myself on being an organized and proactive person, but will admit that I've often found myself procrastinating when it comes to vacation planning  - the  thought of digging through reviews, booking accommodations, and building an itinerary just too overwhelming to consider.

And then... ChatGPT entered the picture.

Over the past few months I've been experimenting with ChatGPT and it's various use cases - so when it came time to plan my summer vacation in Costa Rica, I knew I had to put it to the test. Could Chatgpt act as my personal travel agent?

It could... and it did.

Having my entire vacation planned out for me in mere minutes was a revelation - cutting a major time suck out of my life and  allowing me to actually have FUN while trip planning. And, because it was so helpful for me, I figured I should put together a guide to trip planning with Chatgpt, including how to set up Chatgpt, plan your itinerary,

Getting Started: Setting Up ChatGPT

Before you can begin using ChatGPT to plan your vacation, it's essential to set it up correctly and familiarize yourself with its features. This section will guide you through the process, ensuring you get the most out of your AI-powered travel planning experience.

ChatGPT Subscription?

At the time of writing, OpenAI offers either a free tier or a $20/month subscription. For this task of trip planning, the free tier can work. If you’d like a bit better recommendations and for it to have more recent data (up to September 2021 with GPT-4) then you may want to consider getting the subscription.

Familiarizing Yourself with ChatGPT Features

If this is your first time using ChatGPT or if you have not used it extensively, it’s helpful to understand that a session with it “builds context”. Meaning you can send multiple messages or questions to get better results:

Setting Up Personalized Preferences

To receive the most accurate and relevant travel recommendations, you can seed ChatGPT with what some of your vacation preferences are. This will help the AI better understand your likes, dislikes, budget, and other considerations, resulting in more tailored suggestions. Some preferences you may want to establish include:

Finding Your Destination

When I was recently doing my trip planning, I already had the destinations in mind - and  hadn't even thought to utilize ChatGPT for brainstorming potential destinations.  For the purpose of this article, I set about learning how to get Chat GPT to generate the right destinations for you.

Asking ChatGPT about Potential Destinations


Evaluating Weather and Climate

Maybe you have a strong preference for a certain climate that you’re visiting and specifically at the time of year you’re planning your trip. ChatGPT can provide you with information on the average temperatures, rainfall, and any seasonal considerations to help you choose the best time to visit. Simply ask about the climate conditions during your preferred travel dates to make an informed decision.

Obtaining Information on Travel Restrictions and Requirements

If you’re traveling abroad, you may be curious about any restrictions, such as visa requirements. You could use ChatGPT to find some basic information about travel restrictions to any destinations you’re looking up or maybe you want to ask for destinations where visas are easy to obtain for the country you’re a citizen of. Just be careful to double check as we’re using ChatGPT as a recommendation engine, not as a source of truth.

Crafting Your Itinerary

Similar to creating an outline for an article, creating a rough itinerary for your trip is very easy through ChatGPT and can help you start to plan out activities.

Seeking Recommendations for Activities and Attractions

Again, note that ChatGPT is not operating with the most up to date information, so expect to see some recommendations that may no longer be relevant, such as restaurants that have closed. It also doesn’t have access to any real time ratings or pricing information.


Organizing Your Trip

Once you've identified the activities and attractions you'd like to experience, ChatGPT can help you create a structured schedule for your trip. By sharing the duration of your stay and the items on your to-do list, ChatGPT can generate a proposed itinerary, optimizing your time and ensuring you don't miss any of the highlights. Feel free to ask for adjustments or alternate suggestions, as ChatGPT can easily adapt the schedule to your preferences.

You could also flip this process and first ask ChatGPT for a rough itinerary, and then further ask it for activities based on the outline of the itinerary.


Finding Accommodations & Transportation


ChatGPT can be used to recommend places to stay, but as it cannot access real time information about availability or price, it should only be used if you’re looking for a specific experience. If you’re more looking for a generic, well rated hotel, then you’d be best served using something like

In the future, I expect the capabilities here to increase greatly as ChatGPT’s context increases to more recent information and ChatGPT Plugins are released that will be able to look up things like hotel price + availability. It will even be able to book the hotel rooms for you!


Similar to above, ChatGPT can’t be used to just find you the cheapest flight to book to your destination at the moment, however in the future it will be able to.

What you could use it for however is recommendations related to historical flight prices or potentially how to get around at your destination. You could ask about shuttles, Ubers, renting cars, etc.

Preparing for Your Trip

In preparing to write this article, I used ChatGPT to help outline it. One part of trip planning that I hadn’t even thought about using it for is vacation preparation. The below are more helpful examples of how you could utilize ChatGPT for your adventure mostly written by ChatGPT itself!

Using ChatGPT to Create a Packing List

Packing for a vacation can be a daunting task, but ChatGPT can help you create a comprehensive packing list tailored to your destination and activities. By providing information on the weather, local customs, and your planned activities, ChatGPT will generate a list of essential items to include in your luggage. This ensures you have everything you need for a comfortable and enjoyable trip.

Learning Local Customs and Etiquette

Being aware of local customs and etiquette is important when traveling to a new destination. It helps you respect the local culture and avoid any unintentional offenses. ChatGPT can provide you with information on cultural norms, tipping practices, dress codes, and other essential etiquette tips. This will help you blend in with the locals and enhance your overall travel experience.

Acquiring Basic Language Skills

While English is widely spoken in many countries, learning a few basic phrases in the local language can be incredibly helpful and show respect for the local culture. ChatGPT can teach you essential words and phrases, such as greetings, common questions, and polite expressions. With these language skills in your arsenal, you'll be better equipped to navigate your destination and connect with locals.

Future of Travel Planning

As I’ve mentioned already, ChatGPT is limited by the recency of its context and inability to get real time information. As this changes rapidly over the next several months the usefulness of this strategy to plan a trip will continue to increase. Imagine finding a destination, creating an itinerary, figuring out your accommodations, selecting your activities, and confirming transportation through a tool, which then goes and actually books everything for you.

If this doesn’t find its way into ChatGPT via plugins, someone will build a tool for this that integrates with GPT directly to create a really slick user experience and charges a nominal fee for using it to plan your trip. If you search right now for “AI travel planner” or “chatgpt vacation planning” you can already find some MVP solutions out there.

I hope you find this article helpful in planning your next vacation - be sure to let us know what you think!

Rudy Mutter is a CTO + Founding Partner at Yeti. He found his passion for technology as a youth, spending his childhood developing games and coding websites. Rudy now resides in the Yeti Cave where he architects Yeti’s system and heads up project production.

Follow Rudy on Twitter.

You Might also like...

Man using AI to do marketing workStreamline Your Marketing Strategy with AI and ChatGPT

We're exploring how you can utilize ChatGPT and AI to revolutionize your marketing strategies. Learn how to streamline content creation, boost email open rates, engage your audience, and much more - all while saving an incredible amount of time!

robot and human shaking handsExploring AI's Boundless Possibilities: Highlights From our AI Hackathon

The recent wave of AI technology has had the Yeti team itching to experiment with the countless possibilities it presents - so we organized an AI hackathon that tasked teams with conceiving, designing, and developing an AI powered application… all within a single day. Take a look at what we built!

Developer using AIThe AI Revolution: Transforming Software Development

The Yeti team recently began leveraging with AI development tools, enabling us to streamline our processes, boost productivity, and unlock new levels of innovation - completely transforming the the way we build software products. Learn how you can utilize AI in your Development processes too.

Browse all Blog Articles

Ready for your new product adventure?

Let's Get Started