SimplyVoy vs. TripIt: A Direct Comparison

TripIt has been around long enough that it's the default answer when someone asks "what app do you use for travel?" It's a genuinely useful tool for a specific job — a running list of flights, hotels, and reservations built from your booking confirmations. That job description hasn't changed much in over a decade, and the app hasn't moved much beyond it either.

If you've used TripIt recently and found yourself wanting more — a better sense of what to actually do once you land, a way to split costs with the people you're traveling with, an app that feels like an app and not a scanned-in spreadsheet — this comparison is for you.

Want the short version first? See the feature-by-feature SimplyVoy vs TripIt table.

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First Impressions

Open TripIt and the first thing you notice is that it's built like a website that happens to work on your phone, not an app designed mobile-first. The sign-up flow asks for your birthdate. Trips are listed one after another in a plain vertical stack, with no visual distinction between a weekend trip to Chicago and a three-week trip across four countries — everything blends together the longer your trip history gets.

SimplyVoy is card-based from the ground up. Each trip gets its own card with a cover, dates, and status at a glance, on a layout that was designed for a phone screen first. It's a small thing until you have six trips in your account and need to find the right one in two seconds, not ten.

Creating a Trip: Single-City vs. Real Multi-City Support

This is where the comparison gets specific. TripIt's trip creation flow asks for one city per trip. That's a fine assumption if every trip is "fly somewhere, stay put, fly home" — but it breaks down fast for anyone doing a cruise, a road trip, or a multi-city backpacking route. A 10-day Mediterranean cruise touching six ports doesn't have one city. Neither does a two-week trip through Tokyo, Kyoto, and Osaka.

SimplyVoy handles this natively: each day of a trip can have its own city, and the itinerary — including weather — updates per day accordingly. Day 3 in Rome and Day 7 in Florence are both fully supported inside the same trip, without treating the trip as a single-location event it isn't.

Building the Itinerary

TripIt's "Add a plan" flow asks you to pick an event type first — flight, lodging, activity — then fills in the specific fields that type needs (check-in and check-out for lodging, for instance). It's a reasonable, structured approach, and to TripIt's credit, it's more organized than a free-text entry box would be.

SimplyVoy starts from a different place entirely: forward the actual booking confirmation email, and the itinerary item gets created automatically — dates, times, confirmation numbers, and all — without manually re-typing anything from an email you already received. You can still add items manually when there's no email to forward, but the default path skips the data entry altogether.

The Feature TripIt Doesn't Have: AI That Knows Your Trip

TripIt doesn't offer AI trip planning. It's an excellent record of what you've already booked, but it won't tell you what to do with the four hours between checking out of your hotel and your evening flight.

SimplyVoy's Voy assistant does exactly that. Because it's built from your real itinerary, it knows your actual gaps — not a generic "things to do in [city]" list, but a suggestion sized to the specific window of time you have free, on the specific day it's free. And when the suggestion is an activity, Voy checks Viator's real inventory for a matching bookable tour — real name, rating, price, and a direct booking link, not just an idea.

If you're planning ahead of a trip rather than waiting for Voy's in-app suggestions, browse tours and activities on Viator directly — the same real-inventory search SimplyVoy uses under the hood.

Splitting Costs

TripIt doesn't handle group expenses at all — it's built around individual travel records, not shared trip costs. If you're traveling with other people and need to split a hotel, a rental car, or a group dinner, you're reaching for a second app.

SimplyVoy tracks group expenses natively, in multiple currencies, with even and custom percentage splits for the trips where "split it evenly" doesn't actually fit — then settles who-owes-who with one calculation. One app for the itinerary and the money, instead of two apps that don't talk to each other.

What TripIt Does Fine

To be fair: TripIt's core function — parsing a confirmation email into a clean record — works, and it's been doing it for a long time. If literally all you want is a running list of confirmation numbers with no itinerary planning, no expense splitting, and no AI suggestions, it'll do that job.

Disclosure: SimplyVoy is a Viator affiliate partner — bookings made through the link above may earn us a small commission at no extra cost to you.

Try the Alternative

If you've outgrown "a list of my bookings" and want an actual planning companion — one that fills in the gaps, splits the costs, and looks like it was built this decade — sign up free at simplyvoy.com and forward your next booking confirmation to see the difference firsthand.