Getting my (travel) life organized with TripIt

There was a time in my life when I was known for my sharp memory. For years, my brain was the main tool I used to keep track of flights, hotels, car rentals, and everything else related to our travel bookings. Over time, that steely memory has softened considerably. I now frequently find myself asking questions like, “Did I book a rental car yet…..and if I did, which company did I book?” Those questions started giving me more anxiety than I wanted to have, so I finally got with the program and synced up all of my trips with TripIt and I have to say that I am impressed with how much this tool has improved over the years. To be clear, Frequent Miler doesn’t have any sort of affiliate relationship with TripIt, I’m just finding it really useful and wanted to share for readers who aren’t familiar with it.

A return to TripIt

Despite my once-Elephantesque memory, I was a relatively early adopter of TripIt. My wife and I began traveling extensively many years before we discovered miles and points. Our first extended trip together was about 9 months in Ecuador in 2008-2009 (from which we also visited Peru and Colombia). That was followed by travel around the United States, Asia, and a few months with an apartment in Europe all before we knew what an airline mile was. My parents wanted an easy way to know where we were as we traveled, so I used TripIt and loaded the app to their iPod touch so that they’d know where to contact us in case of an emergency.

I mention that it was pre-miles-and-points because, somewhat ironically, the primary reason I stopped using TripIt was because of the flexibility afforded by miles and points.

Before award travel, I’m not even sure that I knew it was possible to book flights and hotel stays that were refundable / changeable. Every booking got forwarded to TipIt and entered in our travel itineraries and there wasn’t a question about whether we would travel or not since our reservations were all “use-it-or-lose-it” style. TripIt maintains the trip history, so I can go back as far as 2011 and see just how extensively we used TripIt up until about 2016.

As we began traveling more with miles and points, we started making a lot more speculative bookings and found ourselves often changing or cancelling trips. That became a bit of a pain point because I would have to manually delete cancelled stuff from TripIt. I became hesitant to add trips to TripIt until I was sure we were making a trip since things like flights and hotels would often change and TripIt would quickly become a mess. That hesitancy often led to forgetting to forward travel plans at all since there would often be a disconnect of months between booking and solidifying plans. I eventually gave up on TripIt altogether after starting to work here at Frequent Miler back in 2018 (ironically, my last TripIt activity until last summer was a trip that was in progress when I got this job!).

Last summer, we traveled for about 6 straight weeks. With so many moving parts on that trip, I decided to give TripIt a try again. I loved it for that trip, but one trip didn’t make it a long-term habit and I once again fell off the wagon with TripIt.

However, in 2025, we have pretty robust travel plans. Complicating things (in a good way!), we have family members joining us on several of our trips, which means tracking travel plans for five or six or eight people on some trips. Making and tracking all of the arrangements has become a lot to juggle.

Furthermore, whereas I once shied away from TripIt because of the “inconvenience” of needing to manually delete cancelled plans, I’ve now fallen into the difficulty of not being able to remember which backup plans exist and  need to be cancelled. Did I book two cars? An extra hotel room? Do I need to cancel something? When is the deadline?

Enter TripIt for the win.

TripIt basics

TripIt is a pretty simple service that exists in both desktop and mobile app form. There are three simple steps:

1. Sign up for a free account.
2. Forward your booking confirmation emails to plans@tripit.com
3. View all of your trips in easy-to-view timelines on the TripIt.com website or within the TripIt mobile app (available for both iOS and Android) or even send a shareable URL to friends or family who need to see your travel plans.

TripIt pulls information from your booking confirmation emails like dates, times, names, and confirmation numbers and puts them together in an easy-to-view timeline. This even works when forwarding travel plans from multiple email addresses (more on that in a minute). You can view TripIt’s description of how it works here on their site.

TripIt offers a great free service & a paid Pro version

There’s a free version and a paid “TripIt Pro” version. The left column below offers a snippet of the features of the free version. The right column shows some of the add-ons that come with a TripIt Pro subscription. The Pro version has a 30-day free trial and then costs $49 per year (more information is available here).

I’ve been using the free version and I love it. While I could imagine some of the “Pro” features being useful, I’ve found the free version to be so tremendously useful as to not feel a need to upgrade. Since I fly Southwest often, I could see the automated tracking of fare refund opportunities being useful for me, but I haven’t felt compelled to pay $49 per year for the Pro features when the free version has almost everything I want.

You can forward plans from multiple email addresses

One of the things I love about TripIt is that it is possible to forward plans from multiple email addresses. I use different email addresses depending on booking channels and some things get booked out of my wife’s accounts. I love that it is possible to go into my TripIt account and add multiple email addresses (each address does need to be confirmed before you start forwarding itineraries). I have a bunch of email addresses from which I can forward email confirmations and everything syncs up in my TripIt timeline correctly.

Note that the addresses above say “Not Activated”. That’s because TripIt offers a feature to automatically comb your email for travel plans and add them to your TripIt calendar, but I don’t use that feature (I don’t like the idea of giving outside companies access to my email inbox, though some will enjoy the convenience, particularly if you’re organized enough to have nothing but travel plans going to one inbox or another).

Once you forward a booking confirmation email and TripIt has processed it (which usually takes less than a minute), you receive an email confirmation from TripIt that they have received the email and added it to your itinerary.

TripIt works with many different types of travel providers

I have been particularly happy with the range of travel types that TripIt can handle. Whether I forward booking confirmations from online travel agencies, award travel from foreign airline programs, small car rental outfits, Italian train companies, or even cruises, TripIt does an impressively good job parsing out the details.

This flight itinerary from a trip I took in 2017 gives an idea of the level of detail TripIt is able to catalog: within TripIt, I can easily find the flight confirmation number (and copy it with the click of a button!), dates, times, flight numbers, connecting flight information, and more. Clicking on “booking info” offers up other stuff from the email confirmation — in this case, I can see how much we paid in taxes & fees for these award tickets. The level of detail varies a bit, but overall I find that TripIt pulls in and effectively sorts plenty of data.

If TripIt is unable to parse those details, your email gets converted to a PDF and added to an “unfiled items” tab. You can then move the items to the appropriate trip as necessary. It’s worth noting that  I haven’t run into this with anything I’ve sent to TripIt recently.

I was particularly surprised to find that TripIt works smoothly with cruise confirmations!

Since my cruise confirmation emails always come with the cruise details in an attached PDF, I assumed that TripIt wouldn’t be able to do anything with a cruise confirmation email and it would end up “unfiled”. I was wrong!

Last summer, I learned that TripIt could handle cruise emails without a problem. I forwarded an MSC booking confirmation and I was impressed that TripIt not only imported the start and end dates and confirmation information but also split out the dates, times, and locations of port stops!

That was (and is!) massive for me. We don’t book excursions through the cruise line. While planning for activities during a cruise, we have had to repeatedly search our email looking for the booking confirmation to find the attachment with the dates of port stops. Having that information at the tap of an app on my phone’s home screen is a game-changer.  Thanks to the way TripIt breaks the cruise out by day, it’s easy to forward a car rental confirmation and have it show up on the right date on the timeline.

Managing and sharing trips is a breeze

I’ve found TripIt particularly useful when juggling multiple travel plans at once. I find it very helpful to see things on a timeline and to have access to confirmation codes and booking information for everything at the tap of a button. On a multi-stop trip with different hotels, airlines, and rental car companies, this saves me a lot of time that I’d otherwise spend switching between apps and searching emails, which is particularly helpful when you’re tired after a long journey.

For those who like to visualize, you can also view itineraries on a map.

TripIt’s AI is impressively good at figuring out which flights/hotels/rental cars/etc should be linked together as one “trip”, but it isn’t perfect. Sometimes after I have forwarded the booking confirmations for the “outbound” and “return” flights, they’ll end up split out into separate itinerary items. When that happens, TripIt makes it really easy to “Merge Trips” to put things together just as you like.

Sharing trip info is also a breeze. In the screen shot above, you can click on the button that says “manage sharing”. From there, you can add specific people to invite as trip participants or share a public URL for the trip info.

If you choose to send a public URL, it populates an easily viewable itinerary that strips out most personal info like confirmation codes and frequent flyer information.

I find that useful for sharing with family so they can have access to see the trip without having the ability to do any damage by accidentally deleting or changing anything.

Speaking of changing things, you can easily edit details if you need more than TripIt imported or if something isn’t correct. You can also easily add additional notes.

The app provides more info than I need, which is a good thing

The TripIt app covers quite a bit of additional information, much of which I probably won’t use but certainly could be useful.

For instance, if I click on a hotel booking, I can find nearby restaurants, bars, parking, hospitals, etc. I typically use Google Maps to find those things, but it seems that TripIt filters to restaurants with good reviews.

Some may find its safety ratings useful, particularly when staying in an unfamiliar city (although I always try to keep in mind that bad things can happen anywhere at any time). I do like that it breaks out a separate daytime and nighttime safety score.

Scrolling gives further context to the scores and information about particular types of risk that may be useful.

It’s easy enough to use the app to get linked out to Google Maps for transportation options and more. I like that TripIt has focused on making the app as seamless a one-stop-shop as possible. Even though I tend to use stuff like Google Maps to find my transportation options, I like that they integrate it anyway to make it easier on the fly. Like much of what I love about the app, it just adds convenience.

Bottom line

I was a relatively early adopter of TripIt, using it pretty extensively between 2010-2016, but then I fell off the wagon and stopped for years. I’ve recently begun using it again and I love how much it has simplified my trip planning and reduced my anxiety by making all of my plans accessible at the click of a button. I’ve further loved it for Player 2 (my wife) as I’ve loaded the app on her phone as well and now she can easily check for the address of a hotel or see whether we’ve reserved a rental car, etc. Given a robust travel schedule, the ever-growing needs of the family, and an aging brain that just can’t keep everything filed mentally, I am loving the easy access and convenience of TripIt. Maybe I’ll consider the Pro version one of these days, but the free version is quickly once again becoming one of my favorite free tools of the trade. We often say that staying organized is essential in this game, and TripIt is making great strides in helping me organize my travel life.

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