As we prepare for our sabbatical year, one of the most unexpectedly helpful tools in our planning has been AI. Not in a sci‑fi, robot‑assistant kind of way—more like a supercharged research buddy who can sift through mountains of information and give us a starting point when we’re overwhelmed by choices. But like any tool, using AI well is a skill, and it’s one we’re still learning.
I’ve come to realize that using AI effectively isn’t automatic. It takes time, practice, and a bit of curiosity. The quality of what you get back depends heavily on the clarity of what you put in. Crafting good prompts, asking follow‑up questions, and knowing when to trust (or double‑check) the answers are all part of the learning curve.
At the moment, our use of AI is pretty simple and practical:
1. Getting a quick overview of cities
When we’re considering a new destination, we’ll often ask AI for a snapshot:What’s the vibe of the city
What neighborhoods are best for families
What the weather is like during certain months
What the main attractions are
It’s a fast way to get oriented before diving deeper.
2. Comparing destinations
Trying to decide between Osaka and Kyoto? AI can lay out the differences in climate, cost, culture, and logistics in a way that helps us narrow things down.
3. Understanding flight prices and options
AI has been surprisingly helpful for:Explaining typical price ranges
Suggesting the best times to book
Highlighting alternative airports
Breaking down the pros and cons of different routes
It doesn’t replace actual flight‑search tools, but it helps us interpret what we’re seeing.
4. Drafting early itineraries
We’ve used AI a few times to generate a first‑pass itinerary for a city—nothing final, but a great starting point. It helps us see how many days we might want in a place, what activities cluster well together, and what we might otherwise overlook.
5. Worldschooling
I foresee AI being a real help when we get into worldschooling with the girls. It can suggest age appropriate books, movies, and shows that highlight our topic of study. It can create worksheets and suggest games for practicing different skills. Teaching isn’t something I have a lot of practice in, though I certainly am passionate about it. And AI is like a mini experienced teacher giving me tips and keeping it fun.
As we’ve experimented, we’ve discovered even more possibilities:
Organizing logistics
AI can help you:
Build a travel calendar
Track visa requirements
Understand local transportation options
Compare SIM card or eSIM choices
Plan budget estimates for each leg of the trip
Food and local experiences
Ask for: Local dishes to try
Kid‑friendly restaurants
Hidden‑gem cafés
Cultural etiquette tips
Accommodation research
AI can help you refine what you’re looking for before you start searching:
Best neighborhoods for your style
Safety considerations
Typical price ranges
What amenities matter most for your trip
Learning about culture and history
Before arriving somewhere new, AI can give you:
A quick history overview
Cultural norms
Key phrases in the local language
Important festivals or holidays
Here are a few things we’ve learned for using AI effectively in travel planning:
1. Be specific
The more detail you give, the better the output.
Instead of: “What should we do in Lisbon”
Try: “We’re a family with a 6‑year‑old visiting Lisbon for 4 days in June. We love food, history, and easy outdoor activities. What’s a good itinerary?”
2. Ask follow‑up questions
Treat it like a conversation. If something feels off, ask for alternatives or constraints.
3. Cross‑check important details
AI is great for ideas and summaries, but always verify the information it gives you. We have seen a lot of examples where it would reference a store or activity that had been closed down for years or only ran seasonally. And especially with things like visa information, check directly with the source.
4. Use it as a starting point, not the final word
AI shines when it helps you brainstorm, compare, or organize—not when it replaces your own judgment or research.
5. Save your best prompts
Once you find a prompt that works well, reuse it for other destinations. It saves time and keeps your planning consistent.
As we get closer to our sabbatical, I’m excited not just about the travel itself but exploring and learning a little more about AI. It’s already helped us simplify decisions and spark ideas. I’ll be interested in comparing how we’re using it after our year of travel.