Not long ago, the best business calendar in the world was a simple spreadsheet. It might’ve had larger cells and a fancier font than its peers, but it was still the same basic tool – with perks. You want to choose the best online calendar for your business to keep up with the pace of change in 2023.
Today’s online calendars are closer to digital assistants than spreadsheets.
They can share events, schedule meetings, issue reminders, check for conflicts, and even suggest time slots for unscheduled tasks. Without them, most of us would miss appointments, overbook ourselves, and generally get less done.
Chances are, your phone and computer already come with calendar apps — but you are choosing the best online calendar for your business.
Why would you switch calendars or calendar apps? Because every person — and every company — works a bit differently. Some want a plain, streamlined grid system; others are looking for a robust, feature-packed tool that issues reminders and tracks tasks.
Don’t default to a business calendar that’s not right for you or your company. To help you choose the perfect one, we’ve taken the top contenders for a test drive.
Our Criteria for Best Online Calendar for your Business
On our journey, we looked at popular online calendars across three key areas for 2023:
- User interface: A business calendar is a commitment. Before migrating hundreds of events and contacts from your old system, ask yourself: Will I want to use this tool day in and day out?
- Integrations and sharing: Business doesn’t happen in a vacuum. Consider the calendar and productivity apps your team already uses. You don’t necessarily have to choose the same calendar they do, but be sure whichever you pick plays well with their software selections.
- Features and recommendations: There are some features every business calendar should have, like the ability to send event invitations. But each option in this section has some unique features that, depending on your situation, might just sell you on it.
For all categories, we considered the “big three” business calendars — Google Calendar, Microsoft Outlook, and Apple Calendar. We have also given the top up-and-comers their just dues. Within each category, we ranked them according to how we think they stack up against one another.
So which is the best online scheduling option for you? You’re about to find out.
User Interface: Crisp and Clear Wins the Race
There are many ways to do a user interface well, and our options run the gamut:
1. Google Calendar
Free for the web, Android, and iOS.
Stylistically speaking, Google’s calendar offering aligns well with its other tools.
Thanks to an October 2017 refresh, the platform balances design with functionality in a number of ways. Its modern, bright color palette looks good to our eyes, with just enough variance between colors of different event types for an “at a glance” tool. Google also does a nice job of arranging information hierarchically. Important details like dates appear in significantly larger font than nearby text.
Google clearly has its users in mind in other ways as well. Users can see the contact details of meeting participants by simply hovering their cursor over attendees’ names. They can also browse and reserve conference rooms, including capacity and equipment details, directly from the event interface.
One weak point in Google Calendar’s interface? The “week” and “month” toggles. Not only are they listed in two separate locations in the main dashboard, but they’re in a rather small font. What’s more, the drop-down menu in the top right obscures part of the calendar as it’s opened. Then it includes two options — “show weekends” and “show declined events.” These seem out of place on the menu.
2. Microsoft Outlook Calendar
Starts at $6.99 per month for web, Windows, Mac, Android, and iOS.
Of the big three, Microsoft’s online calendar, Office 365 Outlook, might be the least sexy but most visually useful for business people.
Although the main spread looks awfully similar to that of Google Calendar, and the colors are a bit more muted and the fonts tougher to read.
So what do we like about Outlook? In addition to overlaying group schedules, which can also be done in Apple and Google’s calendars, Outlook can display calendars side-by-side. This can come in handy when, for example, you want to compare two coworkers’ calendars without creating a crowded mess on your page. Plus, the side-by-side feature makes it easy to move appointments between displayed calendars.
3. Apple iCloud Calendar
Free for the web, Mac, and iOS.
Apple’s designers clearly chose bare-bones efficiency over design — a reasonable choice for a business calendar. Unfortunately, they seem to have sacrificed some ease of use in the process.
On one hand, we like that the iCloud calendar displays events across multiple calendars, including those offered by competitors. Apple converts whoever uses Google Calendar as a family calendar, for instance. You don’t have to convince the whole family to switch to a new platform.
On the other hand, the iCloud calendar looks downright bland. Compared to Google’s offering, the colors are fainter and the text smaller. All told, it would be much easier to overlook something or double-book yourself in Apple’s calendar.
The other trouble with Apple’s calendar is its notification settings. Although it offers many of the same options as Google Calendar, it doesn’t let users change their default settings across multiple calendars. In other words, iCloud users have to tweak their notification preferences for each and every event. This can be time-consuming and easy to forget about, thinking you’ll do it later.
4. 30 Boxes
Free for the web.
As its name implies, 30 Boxes isn’t much to look at other than a month’s worth of boxes. But the tool has developed something of a cult following for its simplistic design and standout features.
As with the other calendars on this list, 30 Boxes offers daily, weekly, and monthly views. Additionally, however, it displays events in a list called “agenda view.” For events with attached locations, it even plots them on a map.
30 Boxes also make adding events a snap. Neither Google, Apple, nor Microsoft’s options make it possible to add the same event to multiple days by simply picking dates on the calendar. Plus, 30 Books supports natural language entry, which can come in handy in hands-off situations like driving.
Free for the web.
We’d be lying if we said we liked how Zoho looks. Its main spread looks straight out of 2012, and it’s far too grey for our tastes.
Why, then, would Zoho make our list?
Because users who are willing to put in the setup time can customize the interface in any number of ways. Work three-day weeks as a part-time consultant? Zoho can be set for custom work weeks. Work odd hours? Zoho can be set to show only those times on your dashboard.
Like other options on this list, Zoho allows users to subscribe to custom calendars, such as office birthdays. But unlike some others, Zoho makes it easy to share calendars with non-users. Users can export their calendar as a webpage or an ICS document. ICS files work with calendar clients ranging from standards like Google Calendar to smaller players like Mozilla’s Lightning calendar.
Integrations and Sharing: The More, the Better
The look of an online business calendar is, at best, half the story. A calendar software’s functionality depends heavily on which other tools — and how vigorously — it works with other preferences. So how do our options stack up?
Free for the web; paid plans range from $8 to more than $80 per month.
Believe it or not, the best calendar for integrations is the newest contender of the five.
Unlike the other four, Teamup was designed for groups rather than individuals. Used by NASA, Teamup doesn’t require users to create accounts or register whatsoever.
How does Teamup work? When someone creates a Teamup calendar, they’re provided with a unique URL that they can share it with their team. Depending on the creator’s access rules, users can then update the shared calendar as needed. The system works well for everything from scheduling shift workers to managing deliveries.
Although users can create calendars anonymously, those who sign up can import events from Microsoft Outlook, Google Calendar, Yahoo calendar, and more. The tool also integrates with Facebook and Twitter, where users can post calendars in groups or on their own profile pages. Best of all — and unique to this list — Teamup integrates with Slack, allowing users to share calendars quickly in group channels.
2. Microsoft Outlook Calendar
Surprisingly, Microsoft’s calendar might be the best of the big three in terms of integrations.
In late 2016, Microsoft rolled out a set of “add-in” tools. Using them in its own departments and external firms, they have developed a slew of Outlook integrations.
As a result, Outlook integrates cleanly with other Microsoft services like Bing, which it taps into when suggesting meeting locations. It also works with Azure to update associated contacts with chain-of-command information and predictions about which other team members they work with most often.
In addition to its in-house integrations, Outlook boasts a wide range of third-party integrations. Using the Trello add-in, for example, users can import events directly into Outlook. Or, with PayPal’s outlook integrations, they can split checks from dinners scheduled through Outlook.
Free for the web, Android, and iOS; paid plans range from $1.99 to $2.99 per month.
Originally developed for the Japanese market, Jorte’s strengths are its mobile-friendliness and integrations. Although Jorte integrates with Microsoft Outlook and Google Calendar, it’s intended to be a standalone tool.
Aside from other calendar software, Jorte’s best native integration is Evernote. Users can attach photos and notes to calendar events, which works well for brainstorms or similar “team” events.
Even better than its Evernote integration, though, is Jorte’s series of quasi-integrations it calls “event calendars.” Provided by partners like The New York Times, Eater, Apple, and Amazon, these calendars display top stories, events, or songs atop the user’s own schedule. Although many are meant for personal use rather than for business, they can come in handy when a lead wants to talk about tonight’s NFL game or eat at a top-rated restaurant.
4. Google Calender
Although Google Calendar does have some native integrations, it’s not quite the plug-and-play platform we’d hoped it would be. It’s also known for syncing problems with Google’s own Android platform.
Some business users will be satisfied with “table stakes” integrations like Calendar’s Gmail hookup, which automatically lists events mentioned in confirmation emails like flights and meetings. Google Calendar also plays nicely with Asana, allowing users of both tools to sync tasks with due dates to their calendar.
But what if you want to save Salesforce events to Google Calendar? Maybe you want to receive a Slack when calendar events approach, or perhaps you don’t want to have to update Airtable with every new event. For those integrations and more, you’ll have to set them up yourself via Zapier or another third-party service.
5. Apple iCloud Calendar
Apple’s calendar offering isn’t the integration powerhouse we’d hoped it would be. Although it works with other services under the iCloud umbrella, even those integrations leave a lot to be desired.
Take iMessage. Although iCloud will scan iMessages and emails for appointments, it takes an extra step or two to get them into the calendar. When it finds a possible match, iCloud merely highlights a section of text that could be relevant to a calendar event and asks what you want to do next.
Then there’s Apple’s frustrating Mac Mail and iPhone contact integration. For some reason, Apple’s calendar won’t send an invite to anyone whose email isn’t already saved to a contact list. Although users can sync contacts from services like Gmail to their iCloud — there’s not an easy answer for people who like to keep their work and business contacts separate.
For pretty much anything out of Apple’s ecosystem, expect to either use a service like Cronify, which works pretty well or create a custom integration.
Features and Recommendations: Creativity Counts
Every online calendar that’s gained a following has something that it does better than its peers. But these five calendars offer at least one feature that their peers don’t have at all:
Free for the web, $4.99 for Android, iPhone, and iPad; $9.99 for Mac.
Developed by Seattle-based software startup Left Coast Logic, SmartDay doesn’t have a particularly strong interface or unique integrations. It does, however, have one incredibly useful feature: automatic task scheduling.
How does it work? Create a master list of tasks, organize them using pre-set filters, and let SmartDay slot them in between your existing appointments. If you get side-tracked by a long conversation with a coworker, for instance, SmartDay adapts by bumping other tasks down. Then, as you check tasks off, it adds those lower on the list into your schedule. If you need more time, you can extend your workday, which gives SmartDay more slots to fill with tasks.
What if you want to pass a task to someone else on your team? Tag him or her on a shared event, and SmartDay will automatically schedule it on his or her calendar. For volunteer-type events, SmartDay integrates with social media for public sharing.
2. Apple iCloud Calendar
In contrast to Google, Apple seems to be more concerned with unique features. Although some of them strike us as novelties, others have obvious business applications.
The first — automated event intelligence — is actually a better iteration of something Outlook also offers. When a user adds an event location, like the name of a restaurant, Apple’s calendar fills in the rest. Not only does it scavenge a street address, but it displays a map and the weather forecast. Best of all, it provides a “time to leave” alert that predicts, given how heavy the traffic is, how long the user’s travel time might be.
Another way Apple’s calendar comes out on top? Data security. Unlike the other online calendars on this list, Apple’s includes end-to-end encryption and promises not to gather any personal data from the user’s computer.
3. Microsoft Outlook
In terms of unique features, Outlook ranks somewhere in between Apple and Google’s offerings. Entrepreneurs and executives will immediately appreciate the first of its two standout features; as for the second — they may need it more than they realize.
The first, bill pay and package delivery reminders, appear on the user’s Outlook calendar automatically when he or she receives a related email. Outlook adds an event for the day the bill or delivery is due, and it provides an email reminder when the event is one or two days away.
The second, SOCKS proxy support, shores up a persistent weakness in business infrastructure: mobile access. Outlook allows administrators to block channels that smartphones and certain tablets use to access the internet. In short, this feature can block hackers from access points that aren’t protected by the company’s own antivirus or firewall systems.
Free for the web, iOS, and Android; paid tiers range from $9.99 to $20.83 per user per month.
If you’ve heard of Trello, you probably know it as a board-based task management tool.
But increasingly, teams are treating it like a calendar with best-in-class task-management features. Content marketing and sales lead tracking are two use cases Trello itself suggests.
Trello’s best calendar feature? Automatic color-coding of cards by their completion status. Green cards are those that are on track. Yellow ones are due within 24 hours. Red ones are past due. Users can override the color coding at any time, however, by checking a box next to the due date.
Within Trello, users can also leave comments on tasks and send one another to-dos. Although Trello might not have the interface or integrations of some of the larger players on this list, its teamwork tools are the best of the bunch.
5. Google Calendar
Although Google Calendar’s interface is arguably the best of the bunch, its integrations and feature set are frankly uninspiring. With that said, it does offer a couple of exclusive features that appeal to the business crowd.
First, Google Calendar invites support rich formatting. Users can link to relevant websites, documents, or presentations within the invite, and recipients can open them directly from the “Event Details” screen. Second, just as Gmail gives users a second or two to retract a sent email, Google Calendar lets users view and restore accidentally deleted invites.
Choosing Your Next Calendar
Although you might have made your decision based on the features above, chances are that you’ve got a hard choice ahead of you. Simplify it by asking yourself whether usability, integrations, or certain features matter most to you.
If, for example, you want a stellar interface and are willing to accept middling integrations, then Google Calendar might be your best bet. What if you need an intra-team calendar above all? You might narrow your choices to SmartDay, Teamup, Trello. Or, say you work somewhere where data security is critical. You might opt for Apple’s calendar or Outlook.
Whichever option you’re leaning toward, don’t forget to talk to your team about the choices. Even CEOs, who arguably have the most autonomy of anyone at a given company, acknowledge that decisions are more effective when they involve more stakeholders. Your colleagues may think of requirements or options you hadn’t considered. You don’t want to force a decision on them, and you certainly don’t want to be the only one using a tool that nobody else will touch.
Even if your team can’t reach a consensus, at least it can agree on one thing: Any online calendar is better than spreadsheet scheduling. Consider the pros and cons of each calendar, and consider which online calendar would be best for your needs. Start using it in 2023.
Updated February 3, 2023
John’s goal in life is to make people’s lives much more productive. Upping productivity allows us to spend more time doing the things we enjoy most. John was recently recognized by Entrepreneur Magazine as being one of the top marketers in the World. John is co-founder and CEO of Calendar.