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.