Readdle’s new Calendars 5 is the iPad’s first truly smart calendar

I’ve reviewed a lot of calendar apps in the past six months. I like to think of them as one of the trends in design, particularly since Apple’s own app seems so disregarded at this point. Ever since Twitter started shutting the doors on third-party developers, it seems like weather and calendar apps have been the “it” things to build.

Most of the development is happening with iPhones, and there are some truly great apps to be had on that side of the iOS playing field. With the iPad though, I hadn’t tried anything that really did much for me. Most of them were boring visually and dry as far as features go. But that all changed recently with Calendars 5 for iPad, the new app from the visionaries over at Readdle.

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Finally, a “Smart Calendar” for iPad

There are a few things I want a modern calendar to do: First of all, it has be an amazing event planner. It has to greatly simplify any interface interaction. The less time I spend tapping on menus to add an event, the better.

Second of all, it has to include an option to translate my natural input, like “Lunch with Steph tomorrow at 1 at Ennio’s,” into an actual event. It has to automatically grab the time and schedule me for “lunch with Steph” at Ennio’s tomorrow at 1pm.

I love calendar apps that integrate with a todo list.

I love calendar apps that integrate with a todo list.

Third of all, it should work well frictionlessly with task managers. I’m grateful for any option, but integration with Reminders at the very least should be given. It’s not enough to simply store tasks locally; in today’s world, where we all carry multiple devices, it has to sync my todo list somewhere up in the cloud.

Thankfully, Readdle accomplishes all these things with the new app. It’s a great planner with a vastly improved interface over Calendars+ (more on that later, of course). It stores all of your events in the cloud, and works with iCloud, CalDav and Google Calendar.

Calendars 5 finally brings natural language parsing to a Readdle app.

Calendars 5 finally brings natural language parsing to a Readdle app.

Calendars has the ability to understand natural language, although it doesn’t always remove prepositions like “from” in events. I scheduled church (what can I say; I’m still traditional) with a friend from 9:30—noon on Sunday, and the event ended up being titled “Church from” with the rest of the information appropriately filled out. I have little doubt this is just a small bug in an otherwise fine app.

Finally, the app integrates with its own local task management system or with Reminders. Integration with Reminders is as smooth as can be, but it isn’t enabled by default, which I think is a little foolish. Turn it on in the Settings. From there, tasks can be managed in their own area of the app, including the ability to easily add or modify existing tasks. You can move a task from one todo list to another just by dragging it, which works really well.

And thankfully, you can also check off any completed Reminders in Calendars 5 (and receive any notifications straight from the app). In short, if you rely on Reminders, you’ll probably never have to open it again.

Task management is particularly robust in Calendars 5.

Task management is particularly robust in Calendars 5.

I’m particularly impressed with the task management feature because even the competition isn’t anywhere near as good. and Cal aren’t as seamless or well-integrated with the OS, and Agenda doesn’t allow you to check off complete tasks within its app (nor does it properly note when a task is completed before the reminder notification; it will alert you regardless). Not to mention that both apps are only available on iPhone.

The bottom line? As far as calendar management goes, I never felt that Readdle’s previous efforts were anything to sneeze at. But as the announcement suggests, Readdle is finally making a calendar app for power users who crave simplicity. I love it. That being said, there’s more to calendar management than pure function. The design is also of the utmost importance.

Designing the Calendar of the Future

The digital realm of iOS is a pretty shifting paradigm, especially when it comes to something like a calendar. My parents still use those old desk-sized calendars. They scribble anything they need to know on one of those, which always sits on their office desk, and any work they’re doing otherwise sits on top of it. Digital calendars can’t be designed with the same use case in mind.

No matter how much things change, some things stay the same.

No matter how much things change, some things stay the same.

From a visual perspective then, it’s a little unfortunate that Readdle doesn’t do too many things with their app that Apple isn’t already doing with the stock iOS Calendar app. I’m not saying that Calendars 5 and Calendar look the same, but Calendars 5 isn’t as intriguing as an app like, Cal or Horizon (my favourite on the iPhone).

In fact, the design for Calendars 5 is sort of bland. It’s unsurprising. It’s easy to navigate, but never particularly inspiring. Like most calendar apps, the weekly view is still a bit of a disaster that involves a lot of scrolling up and down to see entire days. The daily view is very nice, and I love that I can see a list of today’s tasks right then and there.

I'm a big plan of the daily calendar.

I’m a big plan of the daily calendar.

Where the interface succeeds is in its organization of information. There’s never any question of what’s what. Even some specific events, like a scheduled phone call or the gym, get their own icon. The gym, for example, has a barbell icon beside it instead of the typical filled-in circle. And instead of using circles, tasks are always denoted with a square. The squares look like checkboxes, and appropriately, when you check one off, the square literally gets a checkmark just like you would with a real-world todo list.

I always knew where to look with Calendars 5 and never felt lost, which is as nice a thing I can say. In fact, most would argue that means that the design is exactly as it should be. But I, for one, wish Readdle was willing to take a few more risks with their work and really advance the visual design field they way they’re advancing the smart calendar app’s functionality. Despite the fact that the app does away with most skeuomorphism influence, I’d prefer to see an app that really takes advantage of my screen space in unpredictable and exciting ways.

For an app so full of features, the Settings are very easy to navigate and relatively sparse.

For an app so full of features, the Settings are very easy to navigate and relatively sparse.

I also wish that Readdle was willing to try other things that very few people are incorporating. Why not include the forecasted weather at your event’s location? Or even anonymously ping Google Search to find precise addresses for your events as you type in, say, the name of a restaurant? Then tapping on the address and opening it in Maps would autofill the address in, even if I didn’t know it.

And for another thing: Why can’t I choose to open Google Maps instead for directions?

Final Thoughts

Calendars 5 is, for the most part, everything I want in a modern calendar app. It’s smart enough to understand natural language, it makes for a great task manager (and thus a perfect daily planner) and it makes it easy to find all the information I need. It’s the most complete smart calendar app that I’ve used, and is going to be the standard on my iPad home screen (and maybe even my iPhone’s, since the app is universal) from this point out.

But it’s not perfect. I wish it was riskier with its design, and I wish it had just slightly smart natural language parsing algorithms. I wish it tried incorporating elements like weather forecasts to really make it feel like a weather app from the future. It’s not that Calendars 5 isn’t good enough or best in-class; it’s that when something is close to perfect, the minor problems with it seem so much worse. Calendars 5 is the best smart calendar we’ve got right now, but I’m still much more excited about the smart calendar apps I hope are coming soon.


Readdle's new app doesn't take any real design risks, but it packs a ton of features and is the most competent calendar app available for iPad and maybe even iPhone. A must-have.