Comparison · Travel organisers and day counters · 2026

Stretch vs TripIt Pro

TripIt Pro is the best itinerary organiser on either store, at $49 a year. What it never does is count your days, set your exit date or warn you before you overstay. Stretch does that, free. Here is how I would choose.

By David Toniolo, Do a Stretch · Updated 2026-08-29 · Prices and facts checked 2026-08-17 · 8 min read

Who each one is for

Pick TripIt Pro if your travel is flights and hotels: forward the confirmation email, get one clean itinerary, and hear about the gate change before the airline tells you. Pick Stretch if your travel is countries and stays, and you need the days you have left in each. TripIt never counts a day, and plenty of people run both.

The rules Stretch counts with are public, each with a source and checked date: read them.

TL;DR

Feature	Stretch	TripIt Pro	Winner
Day counting	Every country's rule, from one log, free	None — it shows what you booked	Stretch
Visa guidance	Source and checked date on every rule	Notes for 260+ countries	Stretch
Reminders	14, 7, 3 and 1 days before you must leave	Gate changes, check-in, "Go Now"	Split — Stretch for the border
Itinerary parsing	Not a feature	Best in class	TripIt
Price	Counter and alerts free; Stretch+ $49.99/yr	Free tier; Pro $49/yr	Stretch
Platforms and scale	iPhone and Android; not launched	Everywhere; 4.8★, 308K US ratings	TripIt

TripIt is a superb organiser and has been for twenty years. But it stops at "you need a visa" and never counts a day: it does not know you have 23 days of your Schengen 90 left, or when Thailand's stamp expires. That is the job Stretch was built for, and our counter and reminders are free forever, where TripIt's guidance sits behind $49 a year.

Quick verdict

If you want…	Choose
Booking emails turned into a clean itinerary	TripIt (free)
Gate changes, delays, seat and fare alerts	TripIt Pro
The days left, the exit date, the reminders	Stretch
To see where every rule comes from	Stretch
Both — the airport in one, the border in the other	TripIt + Stretch

TripIt Pro at a glance

What it is. The itinerary organiser, from Concur Technologies (SAP Concur). Forward any booking confirmation to plans@tripit.com and it builds a trip with flights, hotels, cars and trains in order, syncs to your calendar and shares with whoever you choose. It is twenty years old and says nearly 20 million people have used it. Pro watches your flights — live status, gate changes, "Go Now" prompts, seat and fare trackers, airport maps, a passport-renewal reminder — and adds Travel Guidance, launched April 2025: visa, documentation, health and safety requirements for 260+ countries, keyed to your stored passport.

Price. The organiser is free, with 3 document uploads per trip. Pro is $49 a year on tripit.com, listed as a $48.99 yearly in-app purchase on both stores, with a 30-day trial and no monthly plan.

Platforms. iPhone, Apple Watch, Android, Wear OS and the web.

Rating. 4.8★ from about 308,000 US App Store ratings (version 20.7.1, 24 July 2026); 4.7★ from about 95,000 ratings and 5M+ downloads on Google Play.

Stretch at a glance

The app. Counts every country on your passports from one log. Log the day you land, in two taps, and it shows the days you have left, sets the date you must be out, and reminds you at 14, 7, 3 and 1 days. It counts limits that reset when you leave and rolling windows like Schengen's 90-in-180, and keeps your e-visas on the stay they cover. That much is free forever, so a lapsed card cannot cause an overstay.

Where the rules come from. Every rule shows its source, the date it was checked and a trust label, and says so when it is not verified — published at doastretch.com/visa for every destination on your passports. Stretch+ ($49.99 a year, 7-day trial) adds Explore, the Visa Desk, GPS logging, tax-day tallies and planning. iPhone and Android — join the waitlist.

Feature comparison

What each app is counting

TripIt counts reservations; the unit is the trip, and it is very good at it. Stretch counts days; its unit is the stay. You entered Spain on the 3rd, so this is what is left of your Schengen 90 across the rolling 180-day window, and this is the last day you can be inside. TripIt has no notion of that window, of a limit that resets when you leave, or of a visa-on-arrival clock. A UK reviewer paying for Pro put it exactly: "only one missing is monitoring the number of days I spend in Schengen during the 180 days." The free calculator does the Schengen half in a browser.

Winner Stretch — TripIt does not count days at all.

Visa guidance, rules, documents and privacy

Credit first: Travel Guidance is a real feature, not a link farm. Once booked, a trip shows whether you need a visa, what documentation and vaccinations apply, insurance rules and a safety rating, from Riskline — upcoming trips only, and if you hold several passports "we select one". Stretch's rules cover every destination on your passports, each with its source, the date it was checked and a trust label, and the rule sits on the stay you are in, so the number ticks down. Documents go the same way: three uploads per trip free on TripIt, 25 on Pro, against no cap here.

Privacy is the same shape. TripIt is an account: you forward your bookings into Concur's cloud, and the App Store label lists location, contact info, identifiers and usage data as linked to you — reasonable for a sync-everywhere itinerary, and the price of it. Stretch has no account and no server of ours, no ads and no analytics; Stretch+ logs borders from on-device GPS you confirm, and turns the same log into tax-day tallies and travel-history PDFs.

Winner Stretch — a rule you can audit, applied to your days, the visa on the stay it covers, and nothing to leak.

Reminders and the exit date

TripIt Pro's reminders are the best in the airport: check in now, leave now, the gate changed, your passport expires within six months. Not one is "you must be out of this country by Thursday". Stretch sets the must-exit date the moment you log an entry, then reminds you before it.

Winner Split — TripIt for the terminal, Stretch for the border. On overstays, only one of them will ever warn you.

Itinerary parsing, flight alerts and scale

This is TripIt's home stretch and we do not pretend to run it. Forward an email and the reservation is filed; Pro then watches the flight and, in one user's words, "notifies me of airline gate changes long before the airline does". Another says the fare monitor "once found me a refund for a flight that saved me $700". It has twenty years and millions of travellers behind it, and a dev team reviewers call "quick to respond and address bugs". Stretch does not read your inbox — a border, logged in two taps, is the input.

Winner TripIt — by a distance on parsing, and on installed base and years in the field.

Price

TripIt's organiser is free and generous; the guidance, the alerts and the extra document slots are $49 a year, and its own four-star reviews say "Pro is overpriced for what it gives you". Our counter, alerts and documents are free forever, and the one paid plan is $49.99 a year. On the one thing both apps do — the entry rule where you are going — Stretch costs nothing.

Winner Split — the top tiers are within a dollar of each other, so it turns on the floor: our safety layer is free, TripIt's guidance is not.

Choose TripIt Pro if you…

want every booking email turned into one itinerary you can share;
fly often enough that gate, delay and fare alerts pay for the $49;
only need a visa or no-visa note against a booked trip, or travel on a company SAP Concur account that includes Pro.

Choose Stretch if you…

enter countries with a number attached — Schengen, Thailand, Japan, Mexico — counted free, from one log;
want the exit date set the day you land and reminders before it, not a note that says "visa-free for 90 days" and leaves the arithmetic to you;
want to see where every rule came from and when it was checked;
want nothing about your movements on anyone's server — no account, no cloud.

Or do what many travellers do: keep TripIt for the airport, and put Stretch next to it for the border.

How we evaluated

What each app counts — reservations, or days — and whether it tells you or waits
Visa guidance depth, and whether each rule carries a source and a checked date
Documents, GPS logging, tax days, and what the privacy label says is linked to you
Price at each product's top published tier, and what the free tier includes, read from tripit.com and both stores on 17 August 2026

Frequently asked questions

Is Stretch better than TripIt Pro?

Yes, for anyone who needs to know how many days they have left in a country, because TripIt does not count days at all. It is the better organiser, and many travellers use both.

Does TripIt count Schengen days or track visa days?

No. It shows your booked trips and, with Travel Guidance, whether your passport needs a visa — but it counts no rolling window, no limit that resets when you leave, no stay allowance. Its own reviewers ask for exactly that.

Is TripIt Pro worth $49 a year?

If you fly often, the flight alerts, seat and fare trackers and airport maps can be worth $49 on their own. For visa guidance and day counting, no: Stretch shows the entry rule with its source and checked date, and counts your days, for free.

Is Stretch free?

Yes. The counter, reminders, documents, logging and the pre-arrival checklist are free forever; only Explore, the Visa Desk, GPS logging, tax tallies and planning are paid (Stretch+, $49.99 a year). TripIt's organiser is free with 3 documents per trip; Travel Guidance and 25 documents are Pro, at $49 a year.

Sources

TripIt pricing — free vs Pro at $49 a year, 3 vs 25 documents per trip: tripit.com/web/pro/pricing (checked 2026-08-17)
TripIt Pro features — 30-day trial, country-specific travel information: tripit.com/web/pro (checked 2026-08-17)
TripIt help centre on Travel Guidance — Riskline, "if multiple passports are saved, we select one": help.tripit.com (checked 2026-08-17)
TripIt blog, 29 April 2025 — 260+ countries, upcoming trips only: tripit.com/web/blog (checked 2026-08-17)
TripIt on the US App Store — 4.8★ (308K), version 20.7.1 of 24 July 2026, "TripIt Pro (1 Year) $48.99", privacy label: apps.apple.com/us/app/tripit-travel-planner/id311035142 (checked 2026-08-17)
TripIt on Google Play — 5M+ downloads, 4.7★ (95K), updated 17 July 2026, renewal $48.99: play.google.com/store/apps/details?id=com.tripit (checked 2026-08-17)
Review quotes come from the App Store listings above, versions 19.7–20.7.1 (2026-08-17)
Our August 2026 market review, TripIt Pro row: docs/product/market-landscape.md
Stretch's rules, with source and checked date: doastretch.com/visa
Stretch pricing and free tier: doastretch.com

Count it, don't carry it

Do a stretch. Don't snap.

The counter, the alerts and your documents are free, forever. Coming to the App Store and Google Play — one email when it lands.