Skylight Calendar Max review: Sidekick kicks this family calendar up a level

Spring is my busy season. Since my kids were old enough to play team sports, the impending arrival of March brings an avalanche of organizational tasks. Practice schedules, game schedules, and snack signups equal so many dates to remember. They arrive in different ways — paper flyers, Excel sheets, text chains, or through yet another team sports app — but somehow never in a Google Calendar link. It’s a trying time.

But this year, I have a new assistant: Sidekick, an AI-powered planning feature for the Skylight Calendar. I just forward every lengthy email to my Sidekick and upload pictures of schedules and spreadsheets to its app. From there, the AI parses the data, packages it into events, and pushes those to my Google Calendar and to my family’s calendars on the big, bright, 27-inch Skylight Calendar Max smart display that’s mounted by our breakfast counter for all to see.

I’m now prepared to tackle two high school sports seasons, along with all the other scheduling chaos that comes with being a busy working parent to two busy teens. It has taken a decade and significant advances in AI to get here, but parents, this is a game-changer.

The Skylight Calendar Max (from $569.99) is a 27-inch, Wi-Fi-connected, touchscreen digital calendar and the biggest of a family of three that includes a 10-inch model ($159.99) and a 15-inch model ($299.99).

The Skylight Calendar is like the wall calendars I’ve struggled with for years, only easier to update without getting dry-erase marker all over my hands. It can import multiple online calendars from Google, Outlook, iCloud, and more, and then color-code them on a big screen where the whole family can see what’s on their plate and know where everyone will be that day.

Along with the calendar, Skylight has tabs for meal planning, lists (shopping, todos, etc.), and a chore chart. An optional $39 annual Skylight Plus subscription lets you use that big screen as a digital photo frame (which the company also makes), adds a rewards system for the chore chart, and brings you Sidekick.

I’ve been testing the Cal Max since July, and $39 a year for the privilege of seeing my photos (which I can do for free on a smart display) felt a bit steep. But the addition of Sidekick to the Plus subscription made the calendar much more useful to me and well worth the money.

Sidekick is an AI-powered “magic import” feature that can turn emails, photos, flyers, spreadsheets, and the like into calendar entries, recipes, and to-do lists with a few taps. It also adds an AI-powered meal-planning feature, though it was way too heavy on the tofu for my tastes.

The Cal Max, the company’s newest model, addresses my chief complaint about the $300 15-inch version I tested previously: the screen just wasn’t large enough to display four people’s schedules at a glance, and the low-quality display was hard to see at some angles.

In addition to being big enough for multiple schedules (I have nine calendars on the display), the Cal Max has an improved 2560 x 1440 resolution and an antiglare screen. It’s sharp enough to make out the calendar text clearly from most angles, and photos look very nice. One downside is that despite auto-brightness, the screen is a bit too bright at night. Sleep Mode, which lets you schedule when the screen turns off, is helpful, but a dark mode would be very welcome.

Finally, none of the Skylight Calendar models have apps or web access. There are also no smart home controls, microphones, or built-in voice assistants — a selling point for families who find their kids too easily commandeer smart displays to watch YouTube or play Taylor Swift on repeat.

The Cal Max has been useful as a central place for my family to view their schedules and see what everyone else is doing at a glance. My 16-year-old son is allergic to opening his phone’s calendar app, but after two weeks with the Skylight’s 27-inch screen next to his face at breakfast time, he said, “I like how easy it is to just look over and see what I have on today.” If you have teenagers, you’ll understand what high praise this is.

The addition of Sidekick has taken Skylight from a passive organizational aid to an active part of my parental planning arsenal. I started testing the feature this month, and now every event, flyer, or email that contains a date I need to remember is sent off for Sidekick to deal with, greatly helping with my mental load. Last week alone, it saved me about an hour of turning three lengthy practice and game schedules into calendar events.

For those complicated, multi-event entries that are the bane of most parents’ organizational life, Sidekick is a godsend.

It took a one-page flyer of my son’s ball crew schedule for a nine-day tennis tournament and parsed all the information into the correct dates and events, even adding the location.

It turned this sentence into two entries, one on each day, starting at 9AM: “Monday, March 31st, April 1st — Ball crew sign in at 9 am, court schedule to be posted at 10:30 am, (3 courts) (42) Night Match 4:30 sign in.” I would have been really impressed if it had added a second entry at 4:30PM.

After ingesting a document and adding the events, Sidekick lets me check its work, sending an email with the entries it added. A delete button alongside each lets me remove anything it got wrong, or I don’t want.

Of course, there are other AI tools with similar calendar-importing abilities. But I tried sending the same data through both Gemini and ChatGPT, and neither worked as well as Sidekick. Gemini couldn’t parse multiple events for me (it could only handle a flyer with one event on it), and it would only add things to the default Google Calendar associated with the account I was using. With Sidekick, I can select which of my family’s calendars the events I’m adding will sync back to.

ChatGPT did better. It generated an ICS file with instructions on how to import it to my Google Calendar. But while it got the right times, it failed on the locations. The process also required several additional steps compared to Sidekick. And, after generating my ICS file, it informed me I needed to pay $20 a month to do any more.

One big caveat: Skylight only supports two-way sync with Google Calendar or its own built-in calendar service (it has an iOS app that works on a Mac, as well as an Android app and a web interface). Events I add to Skylight, either with Sidekick or on the wall calendar itself, show up on my Google Calendar on my other devices. If you add an event to another online calendar service, either using Sidekick or on the device itself, it will only appear on the wall calendar and in the app; it doesn’t actually add it to your linked calendar.

We’re an iPhone family, but we mostly use Google Calendar, so this isn’t a problem for me. But it’s worth being aware of if your family runs on iCloud or Yahoo calendars or one of the other services Skylight supports.

Sidekick has a few other AI tricks up its sleeve. Its recipe importing is neat. Snap a picture of grandma’s chili recipe or paste a web link, and Sidekick strips out the cruft, saves it neatly in Skylight’s recipe box, and lets you add ingredients to the Skylight shopping list. From there, I can add it to a meal plan and then pull it up on the calendar screen or in the Skylight app to follow along while cooking.

It can also generate a meal plan and export recipes to a shopping list. I tried using this for a week in place of Samsung Food, my current tool for this, but it fell short in several areas.

The AI meal plan didn’t allow for enough customization, and I couldn’t categorize imported recipes; they’re just listed alphabetically. Accessing the recipe box isn’t intuitive. It takes several taps, and it doesn’t allow for selections when adding to the shopping list; it just puts everything on it. (I don’t need four separate instances of “2 tablespoons of olive oil.”) If there were a way to sync recipes, to-do lists, and shopping lists with any apps outside of Skylight, I’d find it more useful; as is, it’s fairly barebones and sandboxed.

The photo frame screensaver is a nice option for when the calendar isn’t in use. But it doesn’t pull from a service like Google Photos; I had to upload pictures from my phone’s camera roll. Wall mounting is the only option for the sizable Cal Max (vertical or horizontal), so it’s nice to have something other than your schedule on display if you have visitors. (Note: You’ll need to make sure you have a good spot for it that’s close to a power outlet. The detachable cable is only 6 feet, so I had to use an extension cord to reach the nearest outlet.)

If you like big screens but not big price tags, there’s also the new Echo Show 21. It has a 21-inch screen and many more functions than Skylight. It’s a smart speaker, smart home hub, and a FireTV — for $400. But if you want a dedicated calendar device, the Echo Show 21 isn’t that. It can’t just show the calendar all the time. It also doesn’t have an AI-powered import function (yet) or work with as many calendar services.

Another more direct competitor to the Skylight Calendar is the Hearth display, which I haven’t tested. It’s the same size as the Skylight, but at $699, it’s more expensive. It does have Hearth Helper, an AI assistant that can import events from flyers and such if you send a photo of it via text. This costs $9 a month ($86.40 a year), almost double Skylight’s fee.

Sidekick brings another level of utility to the Skylight Calendar’s already good hardware. Yes, it’s a big screen running Android, and yes, Gemini and ChatGPT et al. could surpass Sidekick’s schedule parsing abilities one day soon. Yes, it is dependent on Wi-Fi, and if the company goes out of business, you may be left with a big, defunct screen. Skylight tells me if this happened, it “would find a creative way to support all existing products out in the wild.”

But the Skylight team has created a compelling product for corralling the chaos of family schedules. If that’s something you need, and you don’t want to spend time creating a DIY version with a monitor powered by a Raspberry Pi and running DAKboard (as one Verge commenter suggested), this is an out-of-the-box solution that works very well.

Photos by Jennifer Pattison Tuohy / The Verge

(Note: some entries on the calendar images have been blurred for privacy.)