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Hi 👋🏻
Your first international trip is decided. You’re very excited for it before the actual planning begins. Because there are flights to compare, hotels to shortlist, an itinerary to build, and confirmations to track. Before a single booking is made, it already feels like too much.
The good news is that most of this can be handled automatically. You just need to know which tools do what. This newsletter explains exactly that, so planning takes a few hours instead of a few weeks.
How do I find cheap flights without checking every day?
Google Flights has a price tracking feature that does this for you. Search your route, toggle "Track prices" on, and Google sends an email whenever the fare changes. No need to check manually.
One thing worth knowing. The alerts are not instant, so very short-lived deals may be gone before the notification arrives. Checking your tracked flights directly on Google Flights every few days is a good habit alongside the alerts.
The calendar view on Google Flights is also useful if your dates are flexible. It shows fares across an entire month in one grid, so you can see at a glance which days are cheaper on your route.
For hotels, a similar approach works on Booking.com. Lock in a refundable rate early, then keep an eye on the price. If it drops before your trip, rebook at the lower rate and cancel the original.
How do I stop losing booking confirmations across emails and apps?
When a trip is coming up, finding booking details means digging through a pile of emails.
TripIt connects to Gmail or Outlook and does that work for you. Every confirmation email gets picked up automatically and added to one itinerary. No manual work is involved.
For those who prefer not to link their inbox, there is another way. Forward any booking confirmation email directly to [email protected] and TripIt reads it and adds it to your itinerary automatically, just like it would if your inbox was connected.
Can AI actually build a decent itinerary?
Yes, but the prompt matters. For example, asking ChatGPT or Google Gemini for "things to do in Lisbon" returns a generic list. Asking for "a four-day itinerary in Lisbon, staying near Chiado, focused on food and architecture, avoiding touristy spots" gives something far more useful.
For visa requirements and transport options, Gemini is the safer choice since it pulls from live sources rather than older data. That said, do not take the AI-generated itinerary at face value. A place it recommends may have shut down, timings could be off, or the route may not work practically. Treat it as a starting point and verify anything important directly.
Where do I begin if I have never done this before?
Google Flights for tracking fares without checking daily. TripIt or Google Travel for keeping confirmations in one place. ChatGPT or Gemini for building an itinerary without hours of research.
Start with these three and planning becomes a lot less painful.
Thank you!
One thing worth keeping in mind
These tools handle the time-consuming parts. But no app can tell you whether a place is actually worth visiting or whether your itinerary is too packed to enjoy. That part still needs you.
See you on Tuesday!
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