Option 1: Gmail labels and calendar (free, manual)
Create a filter for common senders (airlines, Booking.com, Airbnb, OpenTable) that applies a Travel label. Gmail also auto-detects many flights and hotels and adds them to Google Calendar.
Where it breaks down: labels collect emails, not itineraries. At the airport you’re still searching for “Hertz confirmation” on hotel Wi-Fi. Nothing tells you about a gate change, and a rebooked flight leaves both the old and new confirmations sitting in the label.
Option 2: Forward everything to an itinerary service
Services like TripIt pioneered this: forward each confirmation to a special address and a parser files it into a trip. It works on any platform and needs no inbox access.
Where it breaks down: you have to remember to forward every single email. Miss one and the trip has a hole. Template-based parsers can also fail on unusual formats (small hotels, tour operators), and real-time flight alerts are typically a paid upgrade.
Option 3: Connect your inbox, read-only, to an AI
The zero-effort version: grant read-only access, and the app watches for new confirmations itself. Modern AI extraction reads a booking the way a person would, so the odd formats that break template parsers still work. With TripTidy that looks like:
- Connect once: Gmail, read-only scope, revocable any time. (Prefer not to? Forwarding works too.)
- Trips build themselves: flights, hotels, cars, dinners, and parking are grouped into day-by-day trips; a rebooked flight replaces the old leg with the change noted.
- The itinerary is alive: delay and gate-change alerts (often before the airline’s email), a lock-screen Live Activity on travel day, and your parking confirmation surfacing as you arrive.
The privacy questions to ask first
Inbox access deserves scrutiny. Whatever app you pick, check for all four:
- Read-only scope, revocable at myaccount.google.com/permissions, and adherence to the Google API Limited Use policy.
- Classify and discard: non-travel mail should be dropped at a classification step, never stored.
- No AI training on your email, by the app or its AI provider. It should say so in the privacy policy, in writing.
- One-tap deletion of everything, any time.
TripTidy commits to all four. The specifics are in our privacy policy.
The short version
Labels are free but leave you searching at the worst moment. Forwarding works everywhere but depends on you never forgetting. A read-only AI connection is the only version where the itinerary maintains itself. Pick one that passes the four privacy checks.