TL;DR: Want to plan a trip with ChatGPT/AI?
- Use ChatGPT to brainstorm activities, then turn it into a day-by-day plan with these prompt ideas
- Refine with packing lists, booking links, restaurant suggestions, and rainy day backups
- Save it to Google Docs or use the Live Bold AI Planner for a done-for-you version
1. Why Plan Your Itinerary with AI?
As a solo/couple traveler, I loved spending time planning trips – I would create spreadsheets with links to blog posts for activity ideas, transportation schedules, and accommodation shortlists. I also loved (and still sometimes make) custom google map labels to plot the ideas and come up with the route.
But with little kids around, I do find a lot less time for travel planning. I still love to browse blogs, but more often then not I don’t save them and try to remember the places while we’re traveling or even already on the trip.
As a user experience designer of websites and apps, I’m spending more of more time researching and using AI, so of course the very first thing I did when I tried ChatGPT was use it to help me plan a trip (to St. Thomas with extended family!)
As a parent, I’ve found that AI tools like ChatGPT can significantly streamline travel planning. I’m not alone in this—recent surveys indicate that 70% of Americans are using or open to using AI for trip planning, with the number rising to 81% among families with children. (Source: Lifewire.com, “AI Travel Apps: The Tools Redefining How We Plan Our Trips”)
What surprised me most? ChatGPT isn’t just a brainstorming tool—it can actually structure a full day-by-day itinerary, consider your kid’s nap schedule, and give you ideas you might not have found even after hours of googling.
AI tools are not just a novelty; they’re becoming essential for many travelers. Another survey found that 63% of travelers believe AI makes the planning process more enjoyable and efficient. (Source: rvshare.com, “Travel Planning with AI – Travel Trend Report 2024”)
2. What You Need Before You Start to Plan a Trip with ChatGPT
- A ChatGPT account (or Google Gemini, Claude, etc.)
- Basic trip info: destination, dates, travel style, kids’ ages
- Optional tools to enhance the process:
- Google Docs or Notion for notes
- Google Maps
- Booking sites open in other tabs
If you’re intimated by AI, start with our free how-to PDF: The AI Family Trip Planning Toolkit: Your Guide to Stress-Free Adventures. Learn more here or get the guide below:
3. Step-by-Step: Create a Custom Itinerary Using ChatGPT
Option 1: Start with brainstorming
Step 1: Tell ChatGPT About Your Family and Travel Goals
Start with a clear, detailed prompt. This helps ChatGPT understand your needs and tailor recommendations.
💬 Try this prompt: “We’re a family of four with a 5-year-old and 10-month-old. We’re visiting Portugal for 10 days in April. We love nature, easy hikes, food markets, and avoiding crowds. Can you suggest family-friendly places to visit and activities for each region?”
ChatGPT will often give you a solid list broken down by city or region. From here, you can ask questions about specific items, or ask for more information:
💬 Try this prompt: “For each of those suggestions, provide an estimated cost and link to the official website or Google maps page”
Step 2: Build Your Day-by-Day Plans
Once you have these ideas, ask ChatGPT to shape them into a daily plan.
💬 Try this prompt: “Using the list above, can you create a day-by-day itinerary for a 10-day trip with travel times, downtime, and toddler-friendly pacing included?”
he AI will factor in travel between cities, nap times, and even pacing that avoids early mornings. You might need to include specific instructions to get this information, such as:
💬 Try this prompt: “Include one main activity per day, with suggestions for more if we’re up for it. Include estimated travel time between activities or from [x hotel] and suggested duration for each activity.”
Step 3: Customize with Your Preferences
Here’s where the magic happens. Ask follow-up questions like:
- “Can you swap the beach day for a museum with a kids’ section?”
- “Add restaurant ideas with high chairs or kid’s menus in Porto”
- “Suggest backup rainy day options near Coimbra”
- “Give me links to book a hotel near a kid-friendly beach in Porto”
- “What are the best restaurants with gluten free dishes in Selfoss?”
Option 2: Generate a full itinerary from one prompt
Once you get familiar with building travel itinerary prompts, you might want to start with a comprehensive list of everything you know and want from ChatGPT.
This is the template that I built my Live Bold Guided Trip Planner on, so give it a try to enter this information in a form rather than building your own prompt (uses ChatGPT to generate the response.)
💬 Full itinerary prompt (template): Plan a [#] itinerary in [destination] for [dates] for a family with [travelers], with a focus on [focus]. We prefer [accommodation style], will have [transportation requirements] and our budget is [#]. Also consider [travel preferences]. Include [output requirements]💬 Full itinerary prompt (example): Plan a 3-day itinerary in North Georgia for June for a family with 2 adults, a 5-year-old, and a 1-year-old, with a focus on nature and free kid-friendly activities. We prefer camping or cabins, will be driving and want to keep the trip under $500. Also consider easy hikes less than 2 miles, nice picnic area ideas for lunches. Include breakfast and dinner suggestions, google maps links to all places, and estimated costs.
Next: Use ChatGPT for Packing Lists, Food Ideas, and Local Tips
After you used one of the two prompting scripts to generate your itinerary and ideas, you can refer back to the same chat as you continue to refine, plan, and pack.
Sample prompts:
- “What should we pack for Iceland in July with a 6-month-old and 5-year-old?”
- “Find family-friendly places to eat in Queenstown”
Refine Your Itinerary Over Time
- Ask ChatGPT for weather backup plans, travel time checks, or alternative ideas
- Reuse and edit earlier prompts
4. Tips for Getting the Best Itinerary from ChatGPT
- Be specific in your prompts
- Don’t settle for the first response—treat it like a conversation
- Mention your kids’ needs, travel rhythm, and dealbreakers
- Ask for alternatives, local insights, or links you can vet
Reminder: ChatGPT doesn’t pull from live bookings or real-time maps. Always double-check travel times, costs, ticket availability, etc.
5. Save or Export Your Itinerary
Once you’re happy with your itinerary, you have a few options to reference it for later:
- Leave it in ChatGPT, and return to the chat anytime to scroll through, ask follow up questions, or even get reminders:
💬 Try this prompt: “Remind me what we decided to do on day 5?”
- Create a “project” in ChatGPT to put all trips into a folder. This keeps them organized and, anytime you plan a trip by starting a new chat in the folder, it will remember and reference things that you’ve done.
💬 Try this prompt: “We had a great time in Cancun, build a similar trip for the Bahamas next spring.”
- Copy and paste into Google Docs, Google Sheets, or Notion for sharing and adding your own details like booking numbers and flight times. You might want to print this for offline use
Bonus: Prompts to Create Kids’ Content for Your Trip
You can also ask ChatGPT to take the itinerary and create content for your kids to engage and enjoy the trip even more. Some examples to try:
💬 Try these prompts: “Generate a 5x5 grid with outlined picture of animals for a simple scavenger hunt for our Africa safari” “Rewrite your itinerary into a travel journal for my 5-year-old.” “Create a cartoon journal page of some of our Iceland highlights” “Create a coloring book page from this photo [upload trip photo]”
I’ve had mixed results on the output of these but its always entertaining!
Want It All Done for You? Try Our AI-Powered Family Trip Planner FREE for a Limited Time
If all this sounds great but you want to start with the prompts already entered for you we’ve built a free tool that does just that.
But this isn’t just a form that sends prompts—it was designed for traveling moms and will automatically include kid-centric details we always forget to ask. Like, ‘Where’s the closest playground to the lunch spot?’ or ‘How long will that waterfall hike take with a toddler?’”
Enter your destination, dates, and family travel style—and you’ll get the first draft itinerary instantly. From there, you can refine, save, and email it to yourself for easy access later.
T
his is FREE for a limited time (normally $5 per trip plan or $99/year for unlimited trips).
Final Thoughts: Planning with Confidence, Not Overwhelm
We all want the same thing: a trip that feels just right for our family—not rushed, not cookie-cutter, not overwhelming.
Using ChatGPT isn’t about making your trip robotic. If you know how to prompt it (and now you do!) you can use AI to go beyond the hot-spots and tourist traps and build a once-in-a-lifetime trip focused on making memories and inspiring little travelers.
And if you want a shortcut? That’s what Live Bold is here for.
FAQ: Using ChatGPT to Plan a Custom Family Trip Itinerary
Yes! While it won’t book flights or hotels, ChatGPT can generate detailed day-by-day itineraries based on your destination, interests, and travel style. You can even prompt it to consider kids’ ages, nap schedules, or slow-paced travel.
No—ChatGPT’s free version (GPT-3.5) is powerful enough for most planning tasks. That said, I do pay for the pro plan and use GPT-4 for most queries.
Be specific! Mention your destination, travel dates, ages of your kids, interests, and any must-dos or limitations (like stroller-friendly paths). Treat it like a conversation—ask follow-up questions and refine the results.
Not entirely. ChatGPT is not connected to real-time data like Google Maps or current flight schedules. Use it for ideas and structure, but always verify logistics with trusted sources.
Absolutely! You can ask for customized packing lists (based on location and time of year), food tips, allergy info, translation help, and more.
ChatGPT is a raw tool—you do the prompting. The Live Bold AI Trip Planner wraps that power in a parent-friendly interface. It builds a custom itinerary based on your preferences, and sends it to your email address for each reference and sharing.
