TripIt excels at organizing bookings automatically while Tripsy offers comprehensive planning with beautiful design. Which approach wins?
"TripIt has helped me stay organized on all of my trips!! It places all of my complex trip details in one well organized location and has served me better than a hundred travel agents!! Plus its lited in a fun way and I've loved being able to go back through a 10 year history of trips remembering each flight, lay over, cruise, car rental, hotel, & excursion with fondness!! Anyone serious about their travel adventures absolutely must have this 5 star travel app!!!!"
"I'll update my review when TripIt fixes their app! I've been using it for years and within the last month it's suddenly gotten all glitchy. The app seems to keep resetting because it won't keep my trips. I've built multiple itineraries and they keep disappearing. I have to be online and reload the app to see my information. I've uninstalled and reinstalled multiple times with no luck. I even put in a support ticket and the response I got back was, 'you can still access trip through the web.'"
One of TripIt’s standout features is its ability to automatically generate travel itineraries. Users simply forward their confirmation emails for flights, hotels, rental cars, and other bookings to plans@tripit.com, and the app organizes all the details into a structured itinerary. For even more convenience, TripIt can sync with email providers like Gmail, Outlook, and Yahoo to detect and import bookings automatically.
This eliminates the need for manual data entry, saving time and reducing the chances of missing important trip details.
TripIt acts as a one-stop hub for all travel-related plans, making it easy to keep track of flights, accommodations, car rentals, restaurant reservations, and activities.
The app consolidates everything into a single, easy-to-read itinerary that updates in real time. Even better, it organizes multiple trips separately, so frequent travelers can quickly switch between upcoming itineraries. This means no more digging through emails or scrambling to find booking details while on the go.
A key advantage of TripIt is that users can access their itineraries even without an internet connection.
This is particularly useful for international travelers who may not always have reliable mobile data or Wi-Fi. Once an itinerary is created, all trip details are stored locally on the device, allowing travelers to check flight information, hotel addresses, and activity schedules anytime, anywhere.
TripIt Pro offers real-time flight alerts, notifying users about delays, gate changes, and cancellations before airlines even send out notifications.
This feature can be a game-changer for frequent flyers, as it helps them adjust plans quickly and avoid unnecessary stress at the airport. Additionally, Pro users get baggage claim details upon landing, reducing the time spent searching for luggage carousels.
If a flight is canceled or delayed, TripIt Pro provides alternative flight options, helping users find a new route to their destination.
This feature is especially useful for business travelers or those on tight schedules, as it eliminates the hassle of searching for backup flights manually. It also provides details on available seats, departure times, and airline contact information, making it easier to rebook quickly.
Navigating large airports can be overwhelming, but TripIt Pro offers interactive airport maps to help users find gates, lounges, restaurants, and other essential services.
Additionally, Pro users receive security line wait times, which can help them plan ahead and avoid unnecessary delays at TSA checkpoints. For those who frequently travel through unfamiliar airports, this feature can make layovers and transfers significantly smoother.
TripIt provides a secure space to store important travel documents, such as passport copies, travel insurance details, and visa information.
Having everything accessible in one app eliminates the need to carry physical copies, reducing the risk of losing crucial documents while traveling. This feature is especially helpful for international travelers who need quick access to paperwork for border crossings or airline check-ins.
TripIt seamlessly integrates with calendar apps like Google Calendar, Outlook, and Apple Calendar.
Once linked, all upcoming trips automatically appear in the user’s schedule, ensuring they never forget flight times, hotel check-ins, or activity bookings. This feature is especially helpful for business travelers who juggle multiple meetings and trips, as it keeps everything aligned in one place.
TripIt Pro includes an expense tracking tool, allowing users to log travel-related costs such as airfare, hotel stays, and dining expenses.
This is particularly beneficial for business travelers who need to submit expense reports. Additionally, TripIt tracks carbon emissions from flights and provides recommendations for offsetting one’s environmental impact. This feature is great for eco-conscious travelers who want to reduce their carbon footprint while flying.
For those traveling with family, friends, or colleagues, TripIt makes it easy to share itineraries so everyone stays informed.
Users can grant others access to their trip details, ensuring that travel companions know the flight schedule, hotel information, and planned activities. This feature is particularly useful for corporate travel, where teams need to stay coordinated on business trips.
TripIt Pro removes all advertisements, providing a cleaner, distraction-free experience. While the free version includes some ads, upgrading to Pro ensures a seamless interface with no interruptions. This is a small but appreciated benefit for users who prefer an uncluttered experience.
Simply forward confirmation emails, and TripIt organizes everything into a neat, easy-to-access itinerary.
Flights, hotels, car rentals, and activities are stored in a single, centralized location.
Get notified about delays, cancellations, gate changes, and baggage claim updates.
Access your itinerary even without an internet connection.
Seamlessly integrates with Google, Outlook, and Apple calendars for easy scheduling.
Many of the best features (like real-time flight alerts and seat tracking) require the paid Pro version.
TripIt scans your inbox for travel confirmations, which some users might find intrusive.
Unlike some competitors, TripIt doesn’t allow you to book flights, hotels, or activities directly within the app.
While functional, the app's layout might feel overwhelming or outdated compared to more modern travel apps.
The Pro version costs $49/year, which might not be worth it for infrequent travelers.
Tripsy's standout feature allows users to forward any travel confirmation email to my@tripsy.app for automatic parsing and organization into detailed itineraries. The system intelligently extracts flight details, hotel bookings, car rentals, and restaurant reservations, then organizes them chronologically within your trip.
This progressive enhancement system improves daily with expanded parser support, making trip creation increasingly effortless. The automation works with most major travel providers and eliminates the tedium of manual data entry.
Tripsy provides seamless connectivity across iPhone, iPad, Mac, and Apple Watch with native app experiences optimized for each platform. Features include Siri Shortcuts integration, interactive Home Screen widgets, Lock Screen complications, Apple Maps deep linking, and full iPad multitasking support with Split View and Slide Over functionality.
The Apple Intelligence integration enables voice commands for trip information and automated workflows, making it feel like a built-in iOS feature rather than a third-party app.
The platform enables unlimited guest invitations for Pro users, allowing complete trip editing permissions for all collaborators without requiring them to have Pro subscriptions. Group members can add activities, modify itineraries, contribute expense details, and access shared documents with real-time synchronization across devices.
The system includes favorite guests functionality for frequent collaborators and advanced filtering options for managing complex group itineraries.
Tripsy centralizes all travel-related materials in one location with unlimited document storage in the Pro version. Users can store emails, reservations, PDFs, images, tickets, and notes with direct import from the Files app, camera capture, and full offline access to all stored materials.
This eliminates the need to juggle multiple apps or dig through email folders while traveling, keeping everything organized and accessible.
The app supports international travel with automatic currency conversion using real exchange rates based on trip dates. Users can create custom expense categories, manage group expense contributions for transparent financial management, and export detailed reports via CSV.
This feature particularly benefits international travelers managing budgets across multiple currencies during complex trips.
Tripsy provides push notifications for gate changes, delays, departure times, terminal assignments, and baggage claim information with intensified monitoring 48 hours before departure.
The system automatically manages timezone changes and displays all timezone information directly in the itinerary, eliminating confusion about local versus home times during travel.
The app implements Apple's native design principles with modal cards, colorful category icons, and customizable backgrounds using Unsplash integration.
Users can create custom routes with estimated travel times, organize activities by proximity, and utilize over 40 activity categories with professionally designed icons for comprehensive trip visualization that makes planning enjoyable.
Integrated 10-day weather forecasts for all trip locations combine with automatic timezone management for comprehensive trip awareness.
The system includes Apple Maps integration for point-of-interest imports with automatic phone numbers and web addresses, plus offline location search functionality that prioritizes hotels and key destinations.
Users can easily migrate existing trips from TripIt and other platforms through dedicated import features. The system maintains formatting and organization while adding Tripsy's enhanced features like collaboration tools and document management. This migration capability reduces friction for users switching from other travel planning platforms.
Complete offline access to itineraries, documents, and trip information ensures functionality without internet connectivity. All forwarded emails and stored documents remain available offline, with optional cloud sync for users who want cross-device synchronization.
This architecture provides security and accessibility for international travel or remote destinations.
Native Apple Watch app provides quick itinerary access through complications and dedicated functionality for travelers who prefer wearable access. Interactive widgets keep important information accessible from the home screen without opening the main app, while Siri integration allows voice commands for finding activities and managing trips.
Experience seamless integration across iPhone, iPad, Mac, and Apple Watch that feels like native iOS functionality rather than a third-party app. iPad users benefit from full multiwindow support and Slide Over multitasking, while Siri integration and interactive widgets provide convenient access without constant app switching.
Simply forward confirmation emails to create detailed itineraries automatically, while intelligent parsing continuously improves to handle more travel providers. The system manages timezone changes, organizes chronologically, and eliminates tedious data entry that plagues other travel planning apps.
Unlike competitors who charge for basic sharing, Tripsy Pro enables unlimited guest invitations with full editing permissions. Everyone can contribute activities, expenses, and notes in real-time while accessing shared documents, transforming chaotic group coordination into streamlined collaboration.
Enjoy planning through customizable interfaces with background images, professional activity icons, and proximity-based sorting that creates logical trip flows. The visual approach makes trip management enjoyable rather than tedious, with modular design letting you customize exactly what information appears.
Your travel data remains secure with optional cloud sync while maintaining full offline functionality for all features. This approach provides peace of mind for security-conscious travelers while ensuring itinerary access in areas with poor connectivity, ideal for international or remote travel.
Users consistently report frequent app hanging, save operations taking up to 4 minutes, and data entry processes requiring extensive time due to system lag. Many describe the app becoming unresponsive during basic operations, forcing workarounds instead of normal save functions, creating frustrating delays that make simple itinerary updates extraordinarily time-consuming.
Tripsy remains exclusively for Apple devices without Android support or functional web editing interface. This fundamental limitation excludes Android users entirely and creates collaboration barriers with mixed-platform groups, forcing complete dependence on Apple hardware for trip management and preventing access from Windows PCs or other devices.
Core functionality like trip sharing, cloud sync, and collaboration requires Pro subscription costing $39-59 annually, while competitors offer similar features free. Users frequently complain the free version provides minimal functionality, making the pricing structure feel restrictive since basic collaboration requires premium subscription.
Users report locations failing to appear in search results, difficulty finding restaurants and lodging, and labor-intensive manual activity addition processes. Flight entry becomes problematic with connecting flights, while the search limitations force users to work around the system rather than benefit from streamlined functionality.
Key features lag behind alternatives, with directions showing static map images instead of turn-by-turn navigation, photos uploading as generic documents without thumbnails, and missing budget tracking available in competing apps. Customer service responsiveness issues compound these problems, with users reporting no response to support requests.
The choice between TripIt and Tripsy ultimately comes down to your travel type and platform preferences. Tripsy offers the more comprehensive planning experience with visual map-based interfaces, collaborative editing, and multi-currency expense tracking that make it particularly appealing for leisure travelers and families. Its modern approach consolidates active trip planning, budget management, and group coordination in ways that TripIt doesn't match.
However, Tripsy's modern features come at significant costs in platform compatibility and reliability. The Apple-only ecosystem requirement, occasional UI bugs, and newer platform stability make it feel more like a premium consumer tool than a dependable business companion. For frequent business travelers or those using Android devices, these limitations pose real constraints.
TripIt prioritizes proven organization and cross-platform reliability over modern planning features. Its industry-leading email parsing works consistently across all devices, offers superior flight tracking with real-time alerts, and provides the stable experience that business travel requires. While it lacks Tripsy's visual planning tools and modern interface, it delivers dependable trip organization without platform restrictions or stability concerns.
The verdict: Choose Tripsy if you're a leisure traveler or family using Apple devices who values modern visual planning and can tolerate occasional bugs for comprehensive trip management features. Choose TripIt if you're a business traveler, use multiple platforms, or need proven reliability for organizing existing bookings with superior flight tracking capabilities.
TripIt is specifically designed for business travelers with features like Concur integration, loyalty program tracking, alternative flight suggestions, and superior flight alerts. It excels at organizing complex business itineraries.
Tripsy is optimized for leisure travel and family trips with collaborative planning, visual maps, multi-currency expense tracking, and group coordination features that make vacation planning easier.
TripIt works on iOS, Android, and web browsers, making it accessible regardless of your device preference.
Tripsy only works within the Apple ecosystem (iPhone, iPad, Mac, Apple Watch). If you or your travel companions use Android devices, Tripsy won't work for everyone.
TripIt offers a good free version for basic organization, with TripIt Pro at $49/year for advanced features like flight alerts and seat tracking.
Tripsy has a free version with limited features and Tripsy Pro at $39.99/year. Uniquely, Tripsy also offers a $199 lifetime plan if you want to avoid recurring subscriptions.
TripIt focuses purely on organizing existing bookings - you book elsewhere, then forward confirmation emails to create organized itineraries. It doesn't help with planning or discovering what to do.
Tripsy excels at active trip planning with visual maps, proximity sorting, collaborative editing, and comprehensive itinerary creation from scratch.
TripIt has proven reliability since 2006 with consistent performance, excellent email parsing accuracy, and dependable flight tracking that business travelers rely on.
Tripsy is a newer platform (major update in 2024) with some reported UI quirks and bugs. While feature-rich, it may be less dependable for critical business travel where consistency is essential.
