Trip planning, especially with friends or family, can be a real pain in the *ss.
You’ve got to:
- Pick dates
- Choose a destination
- Plan the itinerary
- Book accommodation
- Book flights
- Figure out what to pack
It all takes time and piles on the mental load.
When I plan a trip with others, I want it to be smooth and easy. There’s no need to suffer through planning great moments with people. Using AI like ChatGPT can help with destination ideas, but always double-check the details to make sure everything’s accurate.
Choosing dates
When I know I'd like to go on a trip with friends (or family), the next step is to decide when and how long.
For that, ChatGPT or any AI won't help you, there are two simple ways I do it:
Way 1 - for small groups (1-3 people)
If I'm planning a trip with only one or 2-3 people (= small group), we'll just have a quick brainstorm face to face or with a Google meet.
During the chat, the 2 main questions to answer are:
1. When are we all available for our trip?
2. How long we'd like to stay?
Once we find a time slot that fits, we all lock the dates in our agendas ASAP.
Way 2 - for bigger groups (4+ people)
If I'm planning a trip / weekend / vacation with 4+ people, here's what I do:
1. I create a Whatsapp Group with the people I'd like to plan my trip
2. I suggest at least 3-6 dates and post them as a poll with a friendly message
3. I follow up every couple of days until everyone has voted
When there are many people in the group and/or some people have busy schedules, sometimes you need to accept that not everyone will be available at the same time and that's OK. The more people in the group and the more busy they are, the harder it will be to find a period that fits everyone.
Sometimes, waiting to find the perfect timeframe will kill the project. Just let go and accept that Bobby won't come to your trip. He should have been less busy.
Choosing a destination
Sometimes you know exactly where you want to go, sometimes you don't.
Here's what we do when we don't.
Step 1: have a chat with the person(s) you're going with, or with yourself if you're alone
When we don’t know where to go, ChatGPT can be super helpful to generate destination ideas and find the best destination.
It can be done following the initial chat to choose the dates.
For bigger groups, if having a chat all together is too difficult, then you can use WhatsApp polls or even create a small form with Tally or Google Forms.
The 4 key questions to answer are:
1. What’s our budget?
- Determine how much you’re willing to spend on transportation, accommodation, food, and activities.
2. What do we want to experience? Examples:
- Road trip
- Relaxing on the beach
- Adventure and sport
- Discovering a city
- Wellness
- Camping
- Nature excursions / hiking
- Staying in a comfy house or hotel
- Food tour
- A mix of multiple experiences
- Anything else you can imagine
3. How far are we willing to travel?
- What's the maximum distance or travel time you’re comfortable with, whether it’s a local getaway or an international adventure.
4. What landscape and climate do we prefer?
- Think about whether you prefer mountains, beaches, forests, urban settings, or rural areas.
- You can also think about your desired climate and temperature: warm, cold, temperate, or variable climate.
Step 2: Prompt ChatGPT to get the best destination ideas
If you don't know where to go yet, here's the prompt that works like a charm to find the best destinations.
Replace your profile and criteria with your information. Remove or add anything you want. Play with it.
You're an absolute master at recommending the best travel destinations based on the profile of your customers and their criteria.
You know all the regions of the world and can recommend any place, be it well-known or lesser-known, as long as it perfectly matches your customers' profile and criteria.
Here's our profile and criteria:
- We're 3 friends of 28, 32 and 23 years old and we'd like to go on vacation at this period: from August 3 to August 12.
- John lives in Paris, Patrick lives in London and Mary in Geneva.
- Our budget is $1000 per person for the transport
- We love nature, hiking and adventure
- We hate mass tourism and avoid crowds
- We'd like to see beautiful beaches
- We'd like to see stunning landscapes
- We'd like a warm weather, 20°C minimum
- We'd like a mix of relaxing on the beach and doing wonderful hikes
- The destination must be within 12 hours' travel for each of us.
- We want the best of the best and are very demanding
Now I want you to list me your absolute best recommendations based on our profile and criteria. Make sure to take all of them into account, that's important.
List between 3 and 5 destinations and for each of them, explain why you recommend it with the main pros and cons. Use bullet points.
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Here are the destinations suggested by ChatGPT for this prompt, that just matches perfectly what we want:
The above prompt is great to give you the best destination recommendations. Once your list, have a chat with the other persons and vote.
Trip planning: choosing the best travel itinerary
This is my favorite part.
Let’s say you have your destination and you’d like to start the travel planning process to discover the country or a specific region. With the right prompt, ChatGPT can be better than your best travel agent.
The magic travel itinerary ChatGPT prompt
Here’s how we prompted ChatGPT for our Copenhagen and Norway trip. Adapt it with your destination, profile, criteria and desires.
You know Copenhagen and Norway by heart. You know all the spots, both well-known and lesser-known, as long as they perfectly match your customers’ profiles and criteria.
You’re an absolute master at creating the best itineraries / road trips in Norway based on the profile of your customers and their criteria.
We’re going to Copenhagen and Norway from August 23 to September 2.
We’d like to start by visiting Copenhagen for 3 days, discovering the atmosphere of the city, eating well in great places, then go to Norway and do a road trip from Oslo. Then we’d return to Paris from Oslo.
I’d like you to help us draw up our itinerary by telling us the best points of interest for us, things to do and places to see in Norway, taking into account our profile and criteria:
- We’re two french men of 33 and 34 years old, from Paris
- We love nature scenery and authentic experiences
- We want to see breathtaking landscapes
- We’re in a good physical condition and like to explore
- We hate crowds and mass tourism
- We don’t like museums and tourist clichés
- Except Copenhagen, visiting cities is not our priority
- We want the best of the best for us and are very demanding
Now I want you to suggest the best itinerary possible for us. And I want you to take our profile and all our criteria into account. That’s important. Be excellent. Go
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This is the Chat GPT travel agent prompt we used to generate the first version of our route. Developing a rough idea of our desired activities and destinations was both exciting and challenging, but ChatGPT streamlined the process.
Optional but recommended: ask your network for recommendations
To make sure to have an awesome itinerary that works for us, in parallel to playing with ChatGPT and conducting our own research, I ask my network of friends and acquaintances on Instagram but you can do it on any platform.
The goal is simple: make sure you don’t miss the places your friends and acquaintances love that ChatGPT might have overlooked.
It helps challenging the itinerary of ChatGPT and make adjustments if needed.
This is what we’ve recently done to plan our future trip to Copenhagen and Norway.
I published a story on Instagram with the following message:
We’re planning to visit Copenhagen for 3 days and then do a road trip in Norway, starting from Oslo.
Do any of my contacts know Copenhagen and/or have done a road trip in Norway?
We are at the stage of planning the itinerary and are looking for recommendations for the best spots to see.
Thank you 🙏
I also asked specific people who know well my destination by sending them a DM.
And the magic happened, I received several replies and someone even sent me a link to a specific route on Google Maps. He didn’t explain why he had chosen these specific stops, but it’s fine as I have my great ChatGPT assistant to explain me everything.
As this person knows Norway well, I decided to prioritize his recommendations over others.
What I did next is to send a screenshot of the itinerary to ChatGPT with the following Prompt
Here’s a screenshot of an itinerary that was also recommended to me.
I’d like you to comment on it, describe it and think about its relevance to your own itinerary. I want to make the right decisions to get the best route.
ChatGPT then described each spot with its interest and compared the two routes pointing out the advantages and disadvantages of each. It also concluded with recommendations and advised to combine both itineraries.
I said “Yes, give me the best combined route to give us the best of both”.
It came back with an awesome combined route. This is the final version of the itinerary we’ll be using for our trip to Copenhagen and Norway.
Create a Notion or Google Doc to centralize everything and streamline the travel planning process
To have the best organization, we open a Notion page and share it with everyone involved. You can use a Google doc or anything that you prefer.
At this point, we put our dates, copy paste the itinerary inside and move to the next step.
How we book accommodations without hassle
Once you have your destination and route, the next step is to book accommodations.
ChatGPT can even provide valuable hotel suggestions to streamline this process to help you find the perfect hotel, but I didn't try it yet.
This part can be very time consuming, especially if there are several persons in the group, but here's my process to make it as smooth as possible.
For big cities, we ask ChatGPT to suggest the best neighborhoods to stay in
If we’re going to major cities, we want to stay in the best area for us.
Here’s how I prompt ChatGPT for that:
You know Copenhagen by heart. You know all the spots, both well-known and lesser-known, as long as they perfectly match your customers’ profiles and criteria.
We’re planning to stay 3 days in Copenhagen on these dates: from August 15 to August 18.
I’d like you to recommend the best areas to book our accommodation based on our profile and criteria.
- We’re two french men of 33 and 34 years old from Paris
- We’d like to discover the authentic part of Copenhagen and avoid mass touristic places and clichés
- We’d like to stay in an area that is: stylish, authentic and local.
- We’d like to have great places to eat nearby, especially to experience the local cuisine
- We want a neighborhood with easy access to the city’s main points of interest.
- We’d like to avoid crowds and mass tourism
- We’d like to avoid very noisy places
- We want the best of the best and are very demanding
Please take our profile and criteria into account and suggest us the 3 best areas to stay and explain why.
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Once we have the 3 best neighborhoods for us, we know where to search. Let’s move forward.
How we choose the best accommodations without spending days on it
My first question before starting to compare accommodations is always: do we want an Airbnb or a hotel for our family vacation?
Based on that we look on Airbnb and/or on Booking.com.
When we’re a group, we generally proceed as follows:
- Everyone searches for homes in the areas we’ve chosen.
- Everyone enters their top 3 for each destination in the Notion or Google Doc. Optional: list the pros and cons of each accommodation.
- Once everyone has entered their selection, we vote by putting an emoji next to the accommodation we prefer.
Another option if everyone agrees is to choose one person to find accommodations and list them in the Notion or Google Doc for the others to vote on. That requires trusting that person to choose the best places.
Once everyone has voted, one or more people book the Airbnbs or hotels.
We usually prefer one person to take care of all the bookings and then we use Lydia, Revolut or a bank transfer to reimburse them.
After booking, we update the Notion or Google Doc to list the confirmed accommodations.
Booking flights
To book flights, one of us searches on Skyscanner, Google Flights, Kayak, Kiwi. I personally prefer Skyscanner.
Important tip: once you've identified the best flights, I recommend you book them directly with the airlines to avoid problems with intermediaries.
Deciding what to bring in your bag: a packing list
First, when I travel, I only take one carry-on bag. I’m a one bagger.
I do that for several reasons:
- Lighter weight by packing light
- Mobility: ease of movement, quick transfers
- Peace of mind: no stress of losing your bag
- No waiting at the luggage carousel
- No baggage extra cost
- Easier packaging thanks to fewer items
- Less decision fatigue thanks to fewer items
- Discrete compared to a huge bag
- Greater enjoyment: fewer things to worry about
For more information, I wrote an article on it: The Ultimate One Bag Travel Packing List 3.0
So I know I will carry only one bag. Based on that, if I don’t know what to bring, I can ask ChatGPT with the following prompt:
You’re an expert at deciding what to bring in your bag when traveling.
Here’s what you need to know about me:
- I’m going to Copenhagen Norway on these dates: from X to X.
- I’d like to pack light with one bag of 50L max.
- I’m a man of 33 years old.
Here’s what we plan doing:
- Visit Copenhagen for 3 days
- Do some hiking and exercising in Norway
- Stay in Airbnbs or Hotels
- I do not enjoy museums, so I prefer more adventurous activities.
What do I absolutely need to bring for the best travel experience?
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Here's an extract of ChatGPT's answer from this prompt:
With this prompt, ChatGPT will suggest a detailed list of things to bring. The most important part is the type of clothes to bring, based on the climate and temperature during your stay.
Final word
Since we use ChatGPT for travel, the trip planning process is now much smoother and fun. I recommend it.
Before following this process, it could take us super long hours to plan a 10 days trip.
We now have a travel agent in our pocket. That's great.
I hope you found this useful. Much love.