Changelog·Roadmap·Privacy·Terms·Contact
Wayfile v0.6.154 · BETA · built 2026-09-14
Wayfile
FeaturesHow it worksPricingChangelog
Sign in

The itinerary tool for people who actually travel.

Drop a confirmation — PDF, screenshot, photo, or forwarded email — and it becomes a clean, logistics-first itinerary in seconds. No typing, no copy-paste, no “sorry, we couldn’t read this format.”

Built for executives and the assistants who run their calendars. Live flight status. Shared with exactly the people who need it. Nothing else.

Start free trial14-day Pro trial · $79/year after · cancel anytime
The Wayfile trips list: three upcoming trips with destination photos, segment counts, and tags, with filters for status, airline, tag, and passenger down the left.The Wayfile trips list: three upcoming trips with destination photos, segment counts, and tags, with filters for status, airline, tag, and passenger down the left.

How it works

Three steps, none of them typing.

  1. 01

    Send it in.

    Forward the email to your private @wayfile.app address, drag a PDF onto the page, or snap a photo of a printed ticket. Batch a whole folder if you want.

  2. 02

    Wayfile reads it.

    An AI extractor pulls every segment — flights, hotels, trains, cars, dinners, meetings — into structured data. A multi-leg PDF becomes multiple segments. Low-confidence fields are flagged for a five-second review instead of silently being wrong.

  3. 03

    It stays right.

    Airline sends a schedule change? The same confirmation number updates the existing segment. Cancellation email? The segment is marked canceled, not left live. Rebooked leg? Matched by route, not by guessing.

Ingest

If a person can read it, Wayfile can read it.

The parser is AI-first, not template-first — so there is no waiting for “support for your airline.” Every format is covered on day one, including the ones that only exist on paper.

  • Email forward to a private per-user address. No inbox access is ever requested — see privacy.
  • PDF, PNG, JPG, HEIC — scanned and photographed documents included. No separate OCR step.
  • Drag-and-drop batches, uploaded per file with retry, so one bad file doesn’t sink the rest.
  • Auto-routing to the right existing trip by date and destination, or a new trip if nothing matches.
  • Source document stays attached to the segment. The original PDF is one click away, forever.

Change detection

Bookings change. Your itinerary should notice.

Most tools treat every forwarded email as a new booking and leave you with three copies of the same flight. Wayfile matches on the confirmation number first and the route second.

  • Same confirmation, new times — the existing segment is updated in place, not duplicated.
  • Cancellations mark the segment canceled instead of leaving a ghost flight on the calendar.
  • Rebooked legs are matched by route identity within a ±14-day window, so a moved flight replaces the old one.
  • Needs-review flow — each segment carries a confidence score; uncertain fields are flagged inline, and your corrections are kept against the source document.
  • Fail-soft parsing — if one segment in a twelve-segment PDF fails validation, the other eleven still land.

The itinerary

Every time, in the timezone it happens in.

An itinerary that reads like an ops sheet. Local time and zone on every row — no mental UTC math at 5 AM in a foreign terminal — and the things you actually get asked for, right where you look for them.

One day of a Wayfile itinerary: a hotel checkout in Tokyo, an overnight Singapore Airlines flight showing departure in GMT+9 and arrival in GMT+8, and a hotel check-in in Singapore with two passenger avatars attached.One day of a Wayfile itinerary: a hotel checkout in Tokyo, an overnight Singapore Airlines flight showing departure in GMT+9 and arrival in GMT+8, and a hotel check-in in Singapore with two passenger avatars attached.
A single day: hotel checkout, an overnight flight with departure and arrival zones both shown, and a check-in with the passengers who are on it.
  • Overnight flights render as one journey, with an arrival marker on the next day — not two disconnected cards.
  • Segment detail: confirmation number, seat, cabin, terminal, room type, party size, host — with a confidence score and the source document beside it.
  • Weather at your destination on each day header, and live flight status with a one-click refresh on every flight.
  • Inline edit of any field, plus manual entry for every segment type when there is no document to parse.
  • Print-optimized — a carry-along copy from any trip, without the chrome.

Passengers and permissions

Who is on the trip is not the same question as who can see it.

Most tools conflate “shared with” and “traveling with.” Wayfile keeps them separate: passengers (PAX) are a first-class part of every trip and every segment, and access is granted independently.

A Wayfile trip header: destination photo, title, dates, tags, passenger avatars, a row of actions (ingest a confirmation, add a segment, share, add to calendar, download PDF, duplicate as template) and a filter-by-passenger control.A Wayfile trip header: destination photo, title, dates, tags, passenger avatars, a row of actions (ingest a confirmation, add a segment, share, add to calendar, download PDF, duplicate as template) and a filter-by-passenger control.
  • Add passengers as existing Wayfile users, invitees, or name-only people who never need an account.
  • Attach per segment — a spouse joins for the last two nights; a colleague is on the outbound only. Every row shows who is on it.
  • Filter by passenger on the trip list and inside a trip.
  • Calendar export scoped to one passenger, so the spouse’s calendar gets the spouse’s segments.
  • Three access levels — Share Limited, Full Read-Only, Full Edit — granted per person, per trip.
  • Cross-account editing without a team plan. Your assistant, chief of staff, or co-principal edits the same trip from their own account. No shared login, no seat to buy.

For the assistant

Second chair, full control.

Wayfile is built around the executive–assistant pair. The assistant does the work from their own account; the principal glances at their phone.

  • Full Edit grants let an assistant manage a principal’s trips end to end without touching their billing or sign-in.
  • Auto-share rules — every new trip goes to the partner or chief of staff automatically, at the access level you choose.
  • Merge trips with segment de-duplication when a booking landed in the wrong one.
  • Duplicate a past trip as a template for the recurring board meeting.
  • Tags — ad-hoc, color-coded, autocompleted from your own history. Filter by tag, passenger, airline, city, date range, or status.
  • Support access is yours to grant. Wayfile staff cannot see your data unless you turn it on, per account.

Getting it out

The itinerary is the source of truth. Everything else subscribes to it.

Wayfile's calendar subscription settings: a live feed URL with options to scope a feed to a tag, to flights only, or to upcoming trips only.Wayfile's calendar subscription settings: a live feed URL with options to scope a feed to a tag, to flights only, or to upcoming trips only.
Calendar feeds — one for everything, one per tag, one for flights only. Each is a URL your calendar polls.
A public Wayfile share link: a read-only itinerary with Add to calendar and Download PDF buttons, no sign-in required.A public Wayfile share link: a read-only itinerary with Add to calendar and Download PDF buttons, no sign-in required.
A share link — read-only, no account needed, stays current as the trip changes, and keeps working offline once opened.
  • Subscribable calendar feeds — a stable .ics URL that Google, Outlook, and Apple Calendar poll. Not a one-time download: the feed updates as bookings change.

Privacy posture

We never ask for your email password.

Wayfile has no Gmail or Outlook sync, at any tier, on purpose. Forward-to-address is the only path from your inbox to Wayfile — which means the only email we ever see is the one you chose to send.

  • No standing access to your mailbox. Nothing to grant, nothing to revoke, nothing to be breached.
  • Set up a forwarding rule once in Gmail or Outlook and it is as hands-off as a sync — without the credentials.
  • Your choice of AI model. Extraction runs on Gemini by default; Pro accounts can route through Anthropic or OpenAI instead — useful when procurement has already approved one provider.
  • Passkeys or magic links. There are no passwords in Wayfile to leak.
  • Deletion means deletion. Deleting your account removes your trips, documents, and workspace.

The full details are in the Privacy Policy.

Compared

What is different.

WayfileTripIt ProTripsy
Reading confirmationsAI-first — any format, day oneTemplate per providerTemplate per provider
Inbox accessNever. Forward-to-address onlyOptional mailbox syncOptional mailbox sync
Passengers vs. permissionsSeparate modelsConflatedConflated
Co-editing a tripCross-account, no team planTeam plan—
Subscribable calendar feedYes, with tag and flight filtersYesYes
Loyalty / points trackingNoYesNo
PlatformWeb (mobile-optimized); iOS in developmentWeb, iOS, AndroidiOS only
Price$79 / year$49 / year$59 / year or $299 lifetime

Pricing

One plan. One price. No seats.

Pro

$79 / year

14-day free trial. Cancel anytime. Everything on this page: AI ingest, forward-to address, live status and alerts, source-document storage, PDF export, calendar feeds, auto-share rules, passenger management.

Start free trial

Free

$0

View any trip shared with you, at whatever access level you were given. Add trips, segments, tags, and passengers by hand. Export your own trips to a calendar. Upgrade whenever a confirmation shows up that you would rather not type.

If a trial ends, nothing is deleted — trips stay visible, enrichment freezes, collaborators keep read access.

Questions

The ones we get asked.

Does Wayfile read my email?
No. Only what you forward to your private address. There is no inbox connection to grant or revoke.
What formats work?
Anything a person could read: airline PDFs, hotel confirmation emails, screenshots of a booking app, a photo of a printed rail ticket. Multi-leg itineraries parse into multiple segments.
What if the parser gets something wrong?
Low-confidence fields are flagged before they are treated as fact. Every field is editable in place, and the original document stays attached so you can check.
Can my assistant manage my trips?
Yes. Grant them Full Edit on your trips — or set an auto-share rule so every new trip goes to them automatically. They work from their own account; no shared login.
My spouse joins for part of the trip. Can they see just their part?
Attach them to the segments they are on and export a calendar scoped to them. A per-passenger share link that shows only their segments is on the roadmap.
Is there a mobile app?
The web app is optimized for phones and works today. A native iOS app is in development.
Does it work offline?
A share link keeps working offline once it has been opened — which is the case that matters on a plane. The signed-in app needs a connection.
Which AI model reads my documents?
Gemini 2.5 Flash by default. Pro accounts can switch to Anthropic or OpenAI from account settings. Documents are sent for extraction only, under API terms that prohibit training on them.
Can I export everything and leave?

Forward one confirmation. See what happens.

Start free trial14 days · $79/year after · cancel anytime
Wayfile

The itinerary tool for people who actually travel.

Product

  • Features
  • Pricing
  • Changelog
  • Roadmap
  • Sign in

Company

  • Privacy Policy
  • Terms of Service
  • hello@wayfile.app
Wayfile2093 Philadelphia Pike #1050Claymont, DE 19703United States
  • Feed filters — tag-scoped, flights-only, upcoming-only. A “Board travel” calendar and an “All flights” calendar from one account.
  • PDF export — a single-page trip summary, designed to be handed to a driver or printed for the folder.
  • Share links for the concierge, the car service, or the family member who will never sign up — with calendar and PDF export built in.
  • Full data export — every record in your account as JSON, any time, from account settings.

    • Competitor details as of August 2026; features change. If you rely on loyalty tracking or need a native app today, TripIt is the better fit.

    Yes. Calendar feeds, PDF, and a full JSON export of your account from settings. Deleting your account permanently removes your trips and documents.