TripIt: Travel Planner

What it does

TripIt is a travel organizer designed to consolidate all trip-related information into a single, coherent itinerary. Users can forward booking confirmation emails or manually input plans like flights, hotels, activities, and restaurant reservations. The app then automatically builds a chronological timeline for each trip, accessible from one dashboard.

Where it shines

TripIt excels at turning scattered information into a structured, useful plan. The manual entry system is surprisingly intelligent. For example, when adding a flight at 02:25, simply entering the flight number auto-populates the departure and arrival airports and times. The true standout feature is its deep utility for day-of-travel needs. At 05:40, the app displays embedded, interactive airport maps directly within the flight details, a huge convenience for navigating terminals without leaving the app.

UX highlights

Structured Itinerary View: The app organizes all plans into a clean, chronological timeline view (03:10), making it easy to see what's next at a glance.
Comprehensive Plan Types: The "Add a Plan" screen (02:10) offers a wide variety of categories, from flights and lodging to concerts and car rentals, ensuring most travel events can be captured.
Intelligent Manual Entry: Even when adding plans manually, the app reduces workload. Entering a venue name like "The Neon Museum" (03:00) auto-fills the address, phone, and website.
Contextual Tooltips: A subtle tooltip appears at 05:31 to guide new users, explaining that they can tap to add documents to their plan, which is a gentle way to educate.
Persistent Action Button: A floating action button (+) is consistently available on the itinerary and trip list screens, making it obvious how to add new plans or trips.

Monetization & growth

Monetization is not pushed during the initial onboarding. Instead, the app focuses on getting the user set up first. A "Tripit Pro" upgrade option is visible in the bottom navigation bar and presented as a full-screen upsell at 06:31. The offer is a single annual plan for $48.99/yr. The screen lists key Pro features like real-time flight alerts, seat tracking, and interactive airport maps. There is no free trial mentioned, indicating a direct-to-paid strategy for its premium features.

Who it’s for

TripIt appears to be for frequent or highly organized travelers who manage complex itineraries. This includes business travelers juggling multiple flights and meetings, as well as vacationers planning multi-stop trips with various bookings. The ability to manually add any type of plan makes it ideal for users who want a single source of truth for their entire journey, from departure to return.

Notes & opportunities

The app's onboarding has a notable point of friction. After creating an account, the user is immediately met with a mandatory modal (00:47) asking for their name and date of birth. While this ensures data quality, it's an abrupt interruption. Testing the integration of these fields into the initial sign-up form could potentially smooth out the first-time user experience. Additionally, the main dashboard's empty state could be more engaging, perhaps with prompts or suggestions for creating a first trip.