TripIt Review: Your Personal Travel Assistant

Are you someone who frequently travels for work or leisure? Do you find yourself juggling various travel bookings, itineraries, and confirmation emails? If so, TripIt may be a good travel organizing app for you to streamline your trip planning process. 

TripIt aims to make travel planning and management as seamless and stress-free as possible, by consolidating all your travel details in one place. In this review, we’ll take a closer look at TripIt’s features, user experience, and pricing.

Basic Features

Booking Details, All in One Place

One of the standout features of TripIt is its ability to automatically pull in booking confirmations from email accounts, eliminating the need for manual data entry. Once you have a TripIt account, you can simply forward your confirmation emails to TripIt ([email protected]), and the app will automatically parse the relevant details, such as flight or hotel reservation numbers, dates, and times. 

Once the app has compiled your travel details, it creates a comprehensive itinerary, which can be accessed offline and shared with others.

The app’s ability to automatically parse travel details is impressive, and in our testing, it correctly identified booking confirmations from a range of airlines, hotels, and car rental companies. You can store information within your TripIt account on:

• Flight bookings
• Hotel and accommodation reservations
• Car rentals
• Restaurant bookings 
• Activities
• Meetings 

Do note that when you first import your flight and hotel bookings into the app, it will often fail to assign them to the same trip (particularly the case when you’re traveling to multiple countries and/or on multiple airlines. 

However, you can easily remedy this with the ‘Merge Trip’ feature, under the ‘More Options’ dropdown on the overview dashboard or individual trip details page.

I did appreciate the app’s ability to combine multiple bookings into a single itinerary, such as a flight and hotel reservation for the same trip. This means that all your travel details are in one place, making it easier to manage and stay organized.

However, there are a few features here that are missing for me, including the ability to view your trip on a calendar layout, or the automatic import of attachments from the email.

Syncs Plans to Your Digital Calendar

TripIt offers multiple ways to integrate your trip itinerary into your calendar, including both a static calendar file and a dynamic calendar feed. The latter is a feature I find very useful.

To use this feature, view your Trip Summary page, then click More Options → Export trip to calendar.

From there, you can download the static calendar file  (.ics), which WILL NOT reflect any changes made on the TripIt app from that point forward (not ideal).

Instead, click on the small hyperlink ‘set up Calendar Feed’ (or find this option separately on the TripIt settings page). 

From this page, you can copy a calendar feed URL for use with various calendar applications including iOS, Android, Apple, Google, and Microsoft Outlook. 

Calendar feeds set up in this way will automatically sync with what is displayed in the TripIt app, giving you one place to update all your trip plans!

Sharing and Group Trip Planner

TripIt offers a few ways to share your trip with others, for example with people who may be traveling with you or just need to know where you will be. 

If you click on ‘Manage Sharing’ from the Trip Summary page, you will see two options, Participants, and Public Sharing. 

With Public Sharing, you get a link that provides view-only access to your Trip Summary. Great for family trips!

On the other hand, you can invite participants to your trip with View or Edit access to modify the trip details and add to the itinerary. This is a perfect feature for travel companions who may also be helping you with bookings or scheduling. 

TripIt Pro – Pricing

The basic version of TripIt is free, and includes all the app’s core features outlined above, such as automatic itinerary creation and real-time flight alerts.

However, for users who want additional features and customization options, TripIt offers a paid version through the TripIt Pro subscription.

TripIt Pro costs $49 per year (USD) and includes several additional features beyond the free version. For example, TripIt Pro includes a feature called “Seat Tracker” which sends you a notification if there is a better seat available for your trip.

Another feature included in TripIt Pro is lounge access information. This feature provides information about airport lounges and their amenities, as well as recommendations for the best lounges based on your itinerary and loyalty programs.

Other features included in TripIt Pro include a points tracker, which helps you keep track of loyalty program points and miles, and VIP travel assistance, which provides 24/7 access to a team of travel experts who can assist with travel emergencies, such as flight cancellations or lost luggage.

Overall, the pricing of TripIt and TripIt Pro is reasonable and competitive compared to other travel organizing apps and services on the market. The basic version of TripIt provides a solid set of features for free, while TripIt Pro offers additional features and customization options for a reasonable annual fee.

You can do a TripIt Pro free trial for 30 days, risk-free. Just cancel before the 30 days are up or you’ll be charged for the year.

Learn about the paid features of TripIt Pro in detail, in the next section.

TripIt Pro – Features

The following set of features is non-exhaustive, but what I consider to be the most important standout features of TripIt Pro. For a full list of features, see the TripIt website.

Note: some features of TripIt Pro web application currently require you to navigate to the ‘Old Website’, when using the web application.

Real-time Flight Alerts

A standout feature of TripIt Pro is its real-time flight alerts. Once you’ve added a flight to your itinerary, TripIt will monitor the flight status and send you notifications about any delays, cancellations, or gate changes. This feature can be particularly useful for business travelers with tight schedules (or points travelers who’ve strung together a set of complicated connecting flights to experience a particular business-class product 😅). It allows you to stay informed and make alternate plans if necessary.

You can choose to receive TripIt flight alerts via email, push and SMS.

Seats, Fares, and Points Tracking

TripIt Pro can be configured to let you know the airfare for a particular flight drops significantly, allowing you to get a refund or credit. 

You can also specify in the ‘Seat Tracker’ you want an alternate seat that isn’t currently available and TripIt will monitor and notify you if it opens up. 

These features could be potentially useful for cash-rate flights, but probably not useful for award bookings. 

On the other hand, TripIt Pro has a Points Tracker, which functions similarly to Award Wallet. This requires you to provide your login credentials for the given program’s website, which may be a bit disconcerting for some.

Like Award Wallet, TripitPro will tell you when your points are set to expire and give you a reminder as the date approaches.

Reminders and Recommendations

Check-in Reminders, Terminal/Gate Reminders, and Commute Times

Within the TripIt app, you can configure ‘Go Now’, which will alert you when it’s time to leave for the airport based on your flight departure time. You can set how many hours before that you want to arrive at the airport, and TripIt will use your location to determine commute time and calculate what time you should leave. TripIt can even send you push notifications regarding what Terminal and Gate your flight departs from. 

Interactive Airport Maps

Only available in the TripIt app, you can find detailed interactive maps of all major airports, including notable landmarks, lounges, restaurants, parking, and so on.

This function can be particularly useful when in a large busy airport that you’re not familiar with. Surprisingly, many airport facilities are not easy to locate, such as when you’re looking for a specific lounge in a specific terminal.  

Apparently, the iOS version of the app is more functional, with a 3D view and automatic adjustment of the level of detail based on zooming in/out. Alas, poor Android users like myself.

Transportation Options and Place Recommendations

You can use a feature called ‘Navigator’ to identify transportation options and costs to destinations on your trip itinerary. For example, you can select a taxi and then immediately be presented with phone numbers for various taxi companies.

The app integrates with popular ride-sharing apps like Uber and Lyft, allowing you to easily book transportation to and from your hotel or airport. 

Furthermore, when viewing a particular location on your trip itinerary, TripIt will provide a browser of nearby places, including restaurants, hospitals, parking, convenience stores, and so on.

Frankly, I find these features have too much overlap with what Google Maps can do, but for anyone who isn’t an advanced maps user, these could have some utility.

Document Upload

While TripIt Free does allow document upload, it only allows 3 documents per trip, which is rather limiting. With TripIt Pro, you can upload up to 25 documents per trip.

Free vs Pro Feature Comparison

Overall User Experience

In terms of user experience, TripIt is a well-designed and easy to use travel app. It has a clean and intuitive interface, with a home screen that displays all your upcoming trips and their corresponding itineraries. From the home screen, you can quickly access trip details, such as flight times or hotel addresses, or view your travel history.

One area where TripIt could improve its user experience is with its app navigation, particularly for its Pro features. While the app’s home screen is straightforward, it can be difficult to find certain features, such as flight alerts or adding a new booking manually. Many of these features require you to switch to the ‘Old Website’ using a button in the top right corner of the screen. It would be helpful if these features were more prominently displayed or linked to from the ‘New Website’, or if there were a more comprehensive menu that included all app functions. 

Another minor issue I encountered with TripIt was occasional syncing errors between the app and email accounts. While the app generally did a good job of automatically parsing booking confirmations, there were a few instances where I had to manually enter booking details. Additionally, I noticed that some flights or hotel reservations were missing from our itinerary, despite being included in the original confirmation email. These syncing errors were relatively infrequent, but they did require some additional effort on my part to correct.

Conclusion

I find TripIt is useful for one simple purpose: consolidating all of your already planned trip information into one location, including transport, accommodation, and activity details. However, as a platform, TripIt is ultimately still a bit inflexible and not customizable for my advanced needs as a points and miles user. 

I would like to see a calendar itinerary view, automatic document upload, and features related to price and costs, to mention a few.

Instead, I’m personally still going to be using Notion to do my detailed trip planning and itinerary building tasks (and hope to share how others can do the same in an upcoming article).  

In the meantime, I think TripIt still has a role for those who want simple consolidation and don’t require too much customization in their trip-building process.

Frequently Asked Questions