I used to fly a lot– in February 2020, just before the Big You Know What, I got an email from Delta telling me that I had crossed the two-million-mile mark with them. I say this not to brag, but to frame a key need I have: effective calendar management around flights. My business travel is starting to pick up again, but the steady drumbeat of news stories and anecdotes about how awful commercial air travel is right now spurred me to mention a few tools and strategies I use for managing this kind of stuff.
First, let’s filter out what I’m not talking about: searching for and pricing flights, choosing a preferred set of travel vendors, etc. The choice of Delta-vs-American (Delta, duh), whether to change planes in Paris vs Amsterdam (Amsterdam, hands down), or whether it’s true that you get the lowest fares when booking on Tuesday (nope)– these are interesting topics for another time but there are also zillions of travel blogs and videos and so on that cover that stuff. Instead, I want to focus on a fundamental issue: how do I track and organize my calendar around travel.
I’ll start with TripIt, because I did start with TripIt. I’ve had it since 2008 and it is an incredibly useful tool for several purposes. First, it’s an all-in-one trip planner. By forwarding airline, train, ship, car, and hotel reservation confirmations to the service, it automatically assembles itineraries and then gives me a simple interface, on web, mobile, and Apple Watch, to show me where I’m going and when, and how much layover time I have at each segment. Here’s an example for a recent trip from Huntsville to Kraków to London to Huntsville.
The basic service is free, but I happily pay $49/year to get the “pro” feature set. This includes push notifications of airport gate changes, flight time changes (both for delays and advances), and a service that will alert you when a purchased airfare drops so you can get it reticketed and recover the difference.
TripIt also has the very useful feature that you can easily share your trips. When I have business travel, it’s easy to share the trip with Erica so she can see my itinerary. Better still, when we’re traveling together, we can both update and edit the itinerary– so while I’m booking flights, cars, and hotels, she can be planning, booking, and adding tours and other activities. Then we both have a complete up-to-date map and timeline of our travel, which we both love.
Then there’s Flighty. This app is pretty much magical. Like Tripit, it tracks flights, and it can notify you of gate changes, delays, cancellations, and so on. In practice, I tend to get notifications from Flighty 5-10 minutes before Tripit. This may not sound like much, but a 5-minute head start on rebooking when your flight’s been suddenly cancelled can be huge.
Flighty can read flight data from TripIt and write it to my iPhone calendar (which in turn is synced with my Exchange Online mailbox). Boom! When I book a flight, it shows up on my calendar with the time zones and locations correct… which means my coworkers can see when I’m in flight, avoiding double-booking. When a flight’s delayed, Flighty’s smart enough to update the calendar on its own. Flighty also ingests FAA delay data, which in itself is super useful. The Flighty app is beautifully designed and their support team is very responsive to feedback.It’s well worth the yearly fee (which I think is $40).
Speaking of FAA delay data… there’s an app for that. Or at least a web site: https://nasstatus.faa.gov/. Lots of people don’t realize how much trouble can be caused by a few storms in inopportune places. Delays at major hubs (like Atlanta, Chicago, or JFK/Newark/LaGuardia) cascade really quickly across the rest of the system–so if there’s a ground stop for bad weather, or storms that reduce traffic flow, or pretty much any ATC-related issue, the delays will spread a lot faster and further than you might expect, often leading to stories in your favorite media outlet with headlines like “travel meltdown.” Although it doesn’t really relate to travel calendar management, I mention this because I usually take a quick look at this page a couple of times on the evening before and morning of my commercial flights. That gives me a sense of what might lie ahead. It’s also my go-to when I have friends or family traveling and I want to keep tabs on whether they are likely to get to their destination on time.
Maybe a future topic: why the Jacksonville Center ATC facility is the biggest single contributor to widespread delays! For now, I’m going to get busy doing the travel expense report I procrastinated to write this.
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